Pico Mountain via Deer Leap Overlook, Long Trail, & Sherburne Pass Trail (Green Mountain National Forest)

Pico Mountain via Deer Leap Overlook, Long Trail, & Sherburne Pass Trail (Green Mountain National Forest)

Hike Type: Loop

Distance: 10.82 miles

Elevation: 3,120 feet

My Time: 4 hours, 49 minutes (4 hours, 42 minutes moving)

Book Time: 6 hours, 58 minutes

Parking: Parking for plenty of cars at Sherburne Pass/Deer Leap trailhead.
Hiking Challenges: New England 50 Finest, Long Trail Side-to-Side

The Hike 

First Day of Summer!

I didn't realize it was the first day of summer until I got here and thought "huh the sun sure is up?" Emma, Sarah, and I got lunch at Martells at The Red Fox near Smuggs, and then I had a scenic (but painfully slow) drive (behind a confused Tesla) through Smuggler's Notch. I wasn't sure what my hiking plans would be, but after scouring the weather I ultimately decided on Pico - a mountain I grew to love this past ski season and one I'd been interested in hiking since I had so much fun skiing it (and it's on the New England Hundred Highest list!). 

I drove past a fox near Stowe and had a shockingly easy drive on I-89. There were some moody skies between Exits 6 and 3 with showers clearly in the distance, but they all seemed to be north of Pico, so I should be fine? I wasn't going to let myself talk myself out of it regardless. Once I was near I drove through a veil of rain that slowly revealed Pico in it's sunny, green glory! I parked at the Sherburne Pass trailhead right at the height of land on Sherburne Pass. It took exactly two episodes of "Love Trapped," the podcast to arrive (I am HOOKED). There were a few other cars (and a van) at the trailhead. It was breezy out with temperatures in the low 70s - I was manifesting dry skies, but I was also accepting that I'd likely get rained on. I got suited up, read the historical marker right at the trailhead, and got my hike started!

"LONG TRAIL LODGE

Long Trail Lodge was built on the south side of Sherburne Pass in 1923 as a gift to the Green Mountain Club by Mortimer Proctor, former club president and later governor of Vermont. The rustic-style clubhouse, built of timber and stone from the site, privided overnight accommodation for members and guests. Managed by Treadway Inns since 1933, it first welcomed skiers for the 1938-39 season and added Deer Leap Chalet as a winter annex in 1938. The lodge remained a popular destination until destroyed by fire in 1968. The Long Trail, conceived by the Green Mountain Club in 1910 and completed in 1930, follows the spine o fthe Green Mountains from Massachusetts to the Canadian broder. The original route of the trail passed dthrough the lodge.

Vermont Division for Historic Preservation - 2024" from Historical Sign on US-4

[2:48pm - Start of Hike]

[2:49pm - Sherburne Pass Trail]

I started by RUNNING across US-4 towards the Long Trail Lodge and entered the woods on the right toward the Sherburne Pass Trail and Deer Leap. There was a split in the trail, with a climber's route on the left and the hiking trail on the right. I entered the woods, relieved myself, realized I hadn't started my watch, and almost followed an old section of abandoned trail - doing great! The Sherbune Pass Trail was pretty rugged without gaining much elevation with super steep cliffs up on the left. I hiked past a bunch of really cool looking rocks and descended slightly. US-4 was super loud even from the trail.

The recent storms had dome some damage to the woods in central Vermont, and there were some VERY recent blowdowns here to show for it! I passed a sign at a low point that encouraged hikers to stay on the trail and to avoid cutting switchbacks. The trail was wet but not nearly as wet as it could have been with recently storms. I crossed paths with a friendly hiking family as I climbed up a steeper and more rugged section, which led to the junction with the Appalachian Trail!

[3:02pm - Appalachian Trail]

[3:03pm - Deer Leap Trail]

I was only on the Appalachian Trail for a minute on a flat stretch and then the Deer Leap Trail started just after. I turned onto the Deer Leap Trail, listening to what I assume was a sportsmen's club in the distance (or at least I hope it was!), and smiled as the sun came out from behind the clouds. I could feel the humidity in the air, but overall it was pretty comfortable. On my journey, I heard what MUST have been a loud truck on US-4... or...

I did check my weather app and it did say that there were storms in the area, but it was looking okay near me? Onward!

The trail climbed a bit more and then leveled out in a wet, but not muddy, section. I heard the mysterious booming truck again, but also an airplane? Strange things were happening in Sherburne Pass! The trail slightly descended to cross some muddy boards before easily climbing again to the junction with the Overlook Spur.

[3:12pm - Deer Leap Overlook Spur]

[3:16pm - Deer Leap Overlook]

I crossed paths with a woman and her puppy at the junction, said my hello, and then continued hiking through some beautiful woods with tree views to Deer Leap Mountain on the right. The trail started to descend, and then descended more (I was being dramatic, it wasn't that much), crossed a couple of bridges, and then opened up to the overlook with truly a spectacular view of Pico! There was a blue "X" on the highet point and I couldn't help but notice a DARK cloud looming behind Pico... The dark cloud started to rumble, so I got myself right back into the woods. I thought I MIGHT get spared based on the wind direction... We'll see...

I had a nice and easy return to the Deer Leap Trail, which would lead 0.9 miles to Willard Gap, per the sign.

[3:21pm - Deer Leap Trail]

The Deer Leap Trail STEEPLY descended from here, and it was clear that most people hike the overlook as an out-and-back. There was a steep, slimy scramble that was a little confusing to follow. I was just happy that I decided to the hike in this direction, so I'll end with an easier descent off of Pico versus having to haul my tired body up this mess. The trail became narrower and buggier, traversing a super wet area and climbing up a little stream. I crossed paths with two... casual hikers, and gave death glares at some screaming blue jays that were yelling at me. 

[3:35pm - Deer Leap Mountain summit area]

I worked my way over a few blowdowns as the trail steepened. I wrote in my notes "this little side quest of mine packs a punch!" The trail skirted the summit cone and left the National Forest Boundary. There were clouds overhead again, but it wasn't like, dark? I was feeling less worried. There WAS a lovely breeze, though!

There were some tree views on the left and cool rocks on the right before the descent really began, and I managed to accidentally follow a steep needly herd path which was NOT the trail. Thankfully, I noticed quickly and soon got back on the real trail. I entered a sea of hip-high ferns, but the footpath was clear. The trail became a muddy stream in a flatter spot, which provided me my first real boot-sucking mud experience of the year!

[3:49pm - Appalachian Trail]

I descended a little bit more and soon came to the Appalachian Trail, which I thought was still both the LT/AT, but nope! I turned left onto the AT right as my watch pinged two miles. Naturally, the trail was much wider now. I walked over a stream through this wonderuflly flat strech of trail, which was a nice break from the down.

[3:53pm - Willard Gap, Maine Junction, & Long Trail/Appalachian Trail]

Soon after, I came to "Maine Junction," which took me too long to realize why it was called that. This is the spot where the Long Trail and Appalachian Trail split! I continued straight onto the LT/AT, the Long Trail Northbound turned right, and there was a closed/abandoned trail on the right. This was also Willard Gap... I think. I noticed there was some construction going on at the junction, too. A gravel foundation bed with two boxes? Maybe a kiosk was going in? I also thought it would be a fun spot for a dual-privy, but probably not that. 

The LT/AT began to descend at very easy grades from this point before gently rising to cross some wet spots and streams. The forest here was really pretty with lush, low undergrowth filling in the space between trees. The trail crossed some form of property boundary before descending again, providing a glimpse through the trees to US-4. I almost stepped on an eft as I was trying to figure out what kind of undergrowth was surrounding me - turns out it was the wood nettle! I've only experienced nettle stings once before, and I do not want to deal with it again! Thankfully I escaped unscathed. 

I was sad that I forgot to bring chapstick with me, but I was happy that the knot in my hip belt was holding strong. I passed some form of a backpacker with an external frame pack in a super wet spot as I continued on into a shadier forest which featured the ROARS of US-4 as a soundtrack.

I passed a few signs (bear country warning, road crossing warning, and a trail relocation warning, even though the trail was relocated in 1999), a few slugs, and another backapcker as I prepared to cross US-4!

"YOU ARE ENTERING BEAR COUNTRY

This area has an active bear population. Bears have approached tents and shelters, eaten hikers' food, and destroyed hikers' equipment.

Observe these guidelines to keep your party safe: 

- Follow all food-storage procedures if staying at designated overnight sites

- Use bear boxes where provided to store food and scented items

- If primitive camping, prepare food and hang bear-bags at least 100 feet from campsites

- Pack out all garbage and food scraps

- Do not feed bears or approach bears

-  If you encounter a bear, do not corner it. Make noise to scare the bear away. Back away slowly.

Please report any bear encounters to the Green Mountain Club by calling (802) 244-7037."

"Caution: road crossing.

Cars on route 4 drive fast.

Wait for a break in traffic.

Walk across the road straight (not on a diagonal)."

"Notice of trail relocation

- The Long Trail and the Appalachian Trail hav ebeen relocated in this area. 

- This relocation puts trails on public land in a permanently proected corridor.

- The former route of the LT/AT remains open and will always be available to the hiking public. It is now called the Sherburne Pass Trail.

- The new LT/AT trailhead is on US 4 one mile west of Sherburne Pass."

[4:14pm - LT/AT crosses US-4]

I, again, SPRINTED across US-4 and got right back onto a trail, which first walked through a wildflower roadside area before turning right to pass more wildflowers (turning left led to a large parking area). I noticed I was also on the Catamount Ski Trail right here as I went back into the woods, passing a kiosk and crossing a bridge over a nice brook.

[4:18pm - LT/AT/Catamount Ski Trail Departs]

The Catamount Trail continued straight ahead as the LT/AT turned left, passing a porcupine warning!

"Dog Danger: Pico is operpopulated with prickly porcupines!

A local ceterinarian reports that he has de-quilled many dogs that were off leash and encountered porcupines on Pico. Apparently the porcupine population population has surged. If you aren't sure your dog knows to avoid porcupines and don't want your hike ruined by an encounter, please leash your dog."

I remembered seeing the same sign when I hiked up Killington last year! The LT/AT continued on flat ground, traversing some boards, and then began to easily gain elevation again. The trail had been really nicely graded at this point. I was back in a similar woods as the other side of US-4, but instead of nettles, it was filled with ferns. There was a nice breeze with many birds singing all around. The humidity was a lot, but thankfully it wasn't too hot out.

I started to catch some afternoon spiderwebs as I maneuvered some more wet spots, eventually crossing with a duo. One of the hikers was manhandling a blowdown off of the trail - thank you, stranger! I began to climb again, still at a reasonable grade. The trail turned with the contour of the mountain, zigging and zagging along. I passed another eft around a section of small streams before rambling through an area full of boulders. There was one spooky cave with room for a couple of folks laying down!

I hurt my own feelings when I checked my progress - I had SO MUCH more to climb! Oh well. I began to climb with steeper switchbacks in a wild area. I could hear running water off to the right as I zig zagged up the mountain, but never actually saw it. There was a nice walking break after a few minutes of climbing and I heard... an airplane? I think it actually was an airplane this time! I eventually crossed the stream that I had been hearing - a wobbly rock almost took me out! I wiggled around some more new blowdowns and then came up to the shelter that I had completely forgotten about!

[5:02pm - Churchill Scott Shelter spur]

I followed the blue blaze to the shelter, but I heard people at the shelter so I just swapped my water bottles at a tentside near the privy and then continued on my merry way! I didn't prepare any water for this hike, so I had to buy a gallon as I drove through Stowe, which was all fine, but I missed my Nuun!

[5:07pm - LT/AT]

Continuing on, I lamented about my climb not even being halfway done, but I think the problem was less that I was tired or bored, but more than my internal hiking clock is not used to hikingin the late afternoon. I did find myself enjoying drinking actual water versus electrolytes... The LT/AT continued to zig zag up the mountain, passing a sunny, overgrown spot with the occasional peek-a-view to who knows what. It was still very hazy outside, but significantly less cloudy. Will I make it out dry? The answer is no, but because I'm sweaty. Rain? We'll see!

I said hello to my third eft of the day as I climbed more consistently toward a false peak-ish area that provided views to the sky through the trees, but I still had a ways to go. The trail passed an overgrown viewpoint and a downy woodpecker before rambling through an area of overgrowth. I was growing impatient/tired as I continued climbing via zig-zags with occasional walking breaks. My watch pinged six miles and I entered a more mixed forest that smelled simply wonderful. The trail leveled out for a bit here - the flat dirt felt amazing on my tired feet. 

I could just barely make out Killington through the trees as the trail began to undulate. I heard either a crow or raven absolutely screaming through the trees. I scraped my way through an area of thin pines with scratchy undergworth (fir wave??) before flattening, descending, flattening again... I was REALLY getting tired of the endlessness! I had to physically crawl under a blowdown and just as I complained about another flat/down, I hit the junction with the Sherburne Pass Trail! Thank goodness.

[5:57pm - Sherburne Pass Trail]

This junction gave me a whole lot of information on a bunch of different signs! It was 0.3 miles to the Pico Camp, 0.7 miles to the Pico Summit, and 3.2 to Sherburne Pass - the three bits I cared about! I could just barely see the top of Pico through the trees and I accepted that I might have to race the sun down the mountain. 

The Sherburne Pass Trail was a narrower blue-blazed trail. To my dismay, I continued to descend through what felt like a wild jungle. 

[6:03pm - Sherbune Pass Trail/Killington-Pico Interconnect]

After a few minutes of descending, the Sherburne Pass Trail crossed the Killington-Pico Interconnect, which was really cool! It's just a wide gravel road, but it felt like I was somewhere where I shouldn't have been, even though it was totally okay! The trail went back into the woods, which were exceptionally moody. I soon passed a "water source down trail" sign, and then I arrived at Pico Camp!

[6:08pm - Pico Camp & Pico Link]

Pico Camp was a small cabin with a closed door, but it didn't looked locked. I was not going to f- around and find out, so I left it alone! There was a privy out in the woods a bit on the same contour. From here, it would be 0.4 miles to the summit!

[6:12pm - Pico Link/Killington-Pico Interconnect]

I climbed up through a rocky stream and then a short, steeper push to cross the Interconnect for a second time, providing a view to Killington through the trees. Back in the woods, the trail continued to be steeper and wet. This push felt like the final push up Killington, even though it was less steep (still steep, to be clear, but the push to Killington was STEEP steep). I crossed paths with a human - the first in a while - and I wrote in my notes that "this climb is a Grade-A doozy."

[6:20pm - Pico Link/Ski Area]

After some questioning of my life choices, I popped out onto the Fourty-Niner ski trail, which I had skied before! I briefly hiked through the woods again before opening up onto the other fork of Fourty-Niner. It was fun to be somewhere I had been before! I worked my way up on the footpath between the tall grasses, which led right to the top of the Sherburne Express Quad, providing a magnificent view. 

[6:24pm - Pico Mountain Summit]

Behind the patrol shack, I spooked a snowshoe hare and found the true summit, marked by a grassy cairn. On a nearby communications tower, some ravens were having a wild conversation. The bugs slowly moved in, surrounding my head in a way that made me feel like I was being swallowed by the air around me. Unpleasant! I throught about skiing the old Poma line and worked my way back to the lift. I loved seeing Abraham, Ellen, Camel's Hump, and Mansfield, and I could see Killington behind me!

[6:36pm - Pico Link]

[6:37pm - Pico Link enters woods]

[6:42pm - Pico Link/Killington-Pico Interconnect]

The bugs quickly went from bad to worse, so I BOOKED it back into the woods. I almost died on some wet spots of the Pico Link, but soon I was running through the Interconnect and back safe at the Pico Camp. I turned left to finish the last bit of the Sherburne Pass Trail.

[6:45pm - Sherburne Pass Trail]

[6:54pm - Sherburne Pass Trail/Summit Glades View]

I passed the water source from a previous trail sign and then the Sherburne Pass Trail began a lovely ramble around the contour. This ramble brought me to one of my favorite trails on Pico - Summit Glades! The view from here was just delightful, especially in the late afternoon sun. The trail actually started descending at this point, and I was thrilled to remember that becuase of how I did this loop, I would be descending significantly less than what I climbed. 

I was feeling an immense sense of joy and gratitude when I realized that not only did I not get struck by lightning on this hike, but I didn't get rained on, AND it turned out to be a stunning afternoon! I hiked down a series of long switchbacks at a reasonable grade and per tradition, the trail then flattened out and crossed 50 streams (more like 5-6). I hiked over a big, bright eft and hurt my own feelings (again) by checking the map (again).

Thankfully a breeze brought me back to life. I was having truly a wonderful time, but I was so upset that it was 7:15pm on a Sunday and I was dreadfully far from home. I then said to myself "don't Monday my Sunday," and I felt better! I crossed a little spur onto the Bushwhacker ski trail, but I didn't bother with it and kept my sights set on the car. 

The trail got wet and slippery afterwards, and after some more hiking turned a corner and I could hear US-4! Naturally, this was the worst section of trail I had hiked all day. I wondered if the upper bit had been relocated, because this was a wet, eroded mess (and I'd later learn that this used to be the Appalachian Trail!). 

[7:35pm - Sherburne Pass Trail/Trail Register]

I arrived at a trail register at a junction with an old, grassy road. I turned left and basically ran out of the woods to the parking area. This was a FANTASTIC hike!

[7:38pm - End of Hike]

As I packed up the car, I noticed someone rock climbing onto Deer Leap! That was fun to see.

I worked my way home, and noticed a lot of damage in the Woodstock area, and then I realized I was driving right through the tornado path! I got a few pictures along the river - the damage was intense. 

I eventually got home just before 11pm. I was TIRED, but what a great day.

Step-by-Step

- Park at Sherbune Pass/Deer Leap trailhead.

- Cross US-4 and start hike on Sherburne Pass Trail (N).

- At terminus, turn left onto Appalachian Trail.

- At jct. just after, turn left onto Deer Leap Trail.

- At jct., turn left onto Deer Leap Overlook.

- At overlook, turn around.

- At terminus, turn left onto Deer Leap Trail.

- At terminus, turn left onto Appalachian Trail.

- At Maine Junction, continue onto Long Trail/Appalachian Trail.

- Cross US-4, continue on LT/AT.

- At jct., turn left onto Sherburne Pass Trail.

- At jct., turn left onto Pico Link.

- Summit Pico Mountain, turn around.

- At terminus of Pico Link, turn left onto Sherburne Pass Trail.

- Follow Sherburne Pass Trail to car.

Map of Coolidge Range

Photo Album

Mt. Ascutney via Futures Trail & Mt. Ascutney Parkway (Mt. Ascutney State Park)

Mt. Ascutney via Futures Trail & Mt. Ascutney Parkway (Mt. Ascutney State Park)

Hike Type: Figure-8-ish Loop

Distance: 10.38 miles

Elevation: 3,051 feet

My Time: 4 hours, 40 minutes (4 hours, 33 minutes moving)

Book Time: 6 hours, 42 minutes

Parking: Parking after first building on right of campground loop (turn left before Mt. Ascutney Parkway and then turn right to start one-way loop, sign for parking on grass, limited parking, $5 fee).
Hiking Challenges: Mt. Ascutney State Park, Operation Alaska Benchmark Challenge, New England 50 Finest

The Hike 

Juneteenth Weekend! I was heading up to Emma's to help her move and do a bucket list hike of mine - hiking from VT-242, over Jay Peak, and all the way to the Canadian Border at Journey's End! Naturally, I planned to sneak a hike in on the way up. I had a late Thursday night followed by an EARLY Friday morning. I had a fever dream of making it to Pitcher Mountain in NH to see the sunrise, but that simply did not work out. My alarm went off at 2:45am and I ended up snoozing until around 3:20am and I was out the door at 3:40am. 

The extra little sleep was beneficial to me - my drive to Hooksett was delightfully not-too-sleepy (minus the last 10 minutes). I apparenly hadn't been to the Hooksett Northbound rest area in a while, because they finished renovating! It looks great and is much more open, now. The bathrooms were closed for cleaning, leaving only the single-stall family restroom open and a line of people. I had to pee, but was going to try to wait. I got gas, started to leave, and turned right around, NEEDING to use the bathroom. Naturally, as I left the bathroom, the main bathrooms opened on up!

My drive along I-89 was mostly on auto-pilot, causing me to miss my exit... twice! I made it to Mt. Ascutney State Park at 6:20am, but spent around 10 minutes trying to understand the parking situation. When you enter the state park and pay your fee, turn left at the Mt. Ascutney Parkway (the auto road). You'll come to the start of a one-way loop, turn right. There will be a building on your right and a small parking sign, park just after the building on the grass. At least that's what I ended up doing and didn't get in trouble (also don't tell them but I only had $2 to throw into the Iron Ranger). 

[6:36am - Start of Hike]

My hike began on the gravel loop road around the campsites. Many folks were waking up and doing their morning camp chores. I happily walked along the road, turning right when the loop turned left. There were a couple of signs for "Futures Trail" that guided me along with my AllTrails. It was beautiful out! It was partly cloudy and just 60 degrees. I continued walking toward a "Dead End" sign, enjoying the smell of morning campfires, and soon came to the actual trailhead of the Futures Trail at the end of the gravel road.

[6:38am - Futures Trail]

I began to follow the Futures Trail, which was blazed with blue rectangles with red dots underneath at first. The trail entered the woods and scooted back behind a couple campsities and passed an old, collapsed chimney before turning away from the campground and pivoting to only blue rectangle blazes.

I worked my way along the trail, which had easy grades, over a few blowdowns and past a rather unhappy turkey. There were a few stone walls covered in moss. I was super proud of myself because I had finally fixed the hip belt on my 32-liter pack, but naturally I put the new buckle on the wrong end of the strap, so now it kept slipping. 

The Futures Trail crossed a logging road and a formerly cleared area on the left with deer prints underneath. There was some sun beginning to poke through the clouds and the tiniest little grey bird with a unique call/sound/song, but I didn't get a photo clear enough to identify it - oh well! The trail crossed another stone wall followed by a swithback that appeared to turn off of an older route. Mentally, I was thinking of this hike as a Pumpelly day on Monadnock - same mountain I've done before, but a longer route and I should focus on the journey.

I hiked past a BIG deer higher up in the woods on the left. It wasn't alerted, but it was watching me intently. The trailbed was delightfully soft and the footing narrowed slightly, but it was nowhere near as bad as Fahenstock (which will be my new comparison point for a while). There was another swtichback at 0.55 miles and then the trail began to steepen with leafy tree views outward that would be nice in winter!

I hit a third and fourth switchback that continued to steepen - this was calf-steep, and in fairness it was more of a wiggle up than a proper series of switchbacks. I did eventually hit a grassy area that was nice a flat before rising again and then crossing another grassy patch that WAS up to my thigh, but nowhere near as dense as Fahnestock. 

I conitnued to alternate between moderate climbs and flat grassy spots. I did eventually put bug spray on just out of caution. The trail slowly got a little rocky and then a little slabby, which I didn't fully trust due to it being just a little wet. At the height-of-land, a spur to the Bare Rock Vista turned left!

[7:08am - Bare Rock Vista]

The spur trail was short and pretty, and the vista was... grown in! I could see out to the valley below through a few trees, and from the right angle I could make out the south and main peaks of Mt. Ascutney, both of which looked far away! I snapped a few photos and then turned around to return to the Futures Trail.

[7:11am - Futures Trail]

While long, I appreciated how the Futures Trail was broken up nicely in different segments. A sign once back on the trail told me that the road crossing was in 1.1 miles, the Steam Donkey was in 2.4, and the Windsor Trail in 3.1 - wonderful pacing if you ask me! From here, the trail descended back into the woods, and descended, and then steeply, and descended... I could hear a train blaring it's horn somewhere not-too-far away, and later a breeze graced my presence and felt absolutely divine.

I had bought two breakfast sandwiches at Hooksett, had one in the car and was going to bring the other one on the hike with me, but I had just realized that I left it in the car! It was literally fine - I also had eaten a loaded hash brown and a TON of cheerios this morning, but I was still a little bummed! I hopped over some deer poop and another blowdown before descending via more switchbacks. The footing continued to be wonderfully soft as I entered a really pretty flat, mossy area. 

The trail began to rise again, passing two sharp pointed rocks. It could have been just two coincidentally placed rocks, or maybe a town line? It looks like the Futures Trail comes near the Windsor/Weathersfield town line in spots? Who knows! I continued to ramble through more easy forest with soft dirt, roots, and rocks, passing singing birds and squirrels doing their morning chores. The trail got a little wet once near a stream, and then the bugs started to act up, too! I passed an eft, and then another! I noticed through the woods I was nearing some form of clearing, maybe the road?

I worked my way around some more wet, mossy rocks, and then confirmed that it was not the road, but a power cut! I came up to a stream, which bordered the power cut, and then climbed alongside both of them. In the process, I spooked two baby ruffed grouses (I saw them fly away and heard their "chirping," which was unfortunately a familiar sound to me. Then, I saw the mother, fully puffed up, charging at me, and hissing! I SCREAMED at it and ran, hopping across the stream and the surrounding wet area, entering the power cut, but soon coming to another screeching hault...

[7:40am - Futures Trail/Power Cut]

...because there was a porcupine right in the middle of the trail! Thankfully, the grouse had ceased it's attack and the porcupine could have not been more unbothered. It munched away at some undergrowth for a minute, and only started to move when I went off-trail to get around it. It casually scooted up a nearby tree - it was a joy to watch! After a few minutes I thanked him for his time and continued on my way.

A sign at the upper parking lot read:

"PORCUPINES IN THE PARK

The North American porcupine is abundant in Mt. Ascutney State Park. Porcupines are rodents, and their hollow quills are modified hairs. They can't throw their quills, but they can lose a few (so be sure to keep your dog safe by following park rules and using a leash at all times). Porcupines eat a large variety of types (and parts) of plants and some insects. You may come across them at night or during the day. We love our porcupines. Please enjoy watching them from a distance." from Trailhead Kiosk

[7:45am - Futures Trail/Parking Area]

Soon after my wildlife debacle, I came to what I thought was the road - not yet! The Futures Trail skirted the edge of a gravel parking area for a picnic area. It passed some sort of shed (maybe a pump house for the water fountain and bathroom across the street?) and then reentered the woods, passing a single pink flower. The clouds had fully rolled in by this point, but it still wasn't supposed to rain. The trail back in the woods was wet, but dried up once I began to climb again.

[8:00am - Futures Trail/Power Cut]

The trail steeply climbed up to cross the power cut again and then continued up for a few minutes before another walking break. This trail was good about alternating climbs with walking breaks! I crossed the power cut one more time during the walking break, catching a little view and wondered if people ski this? From the power cut, the trail easily descended on a wider trail to a wet area, and then officially crossed the paved road, the Mt. Ascutney Parkway!

[8:04am - Futures Trails/Mt. Ascutney Parkway]

Knowing the hardest part of the hike hadn't happened yet, I cautiously thought to myself "ya know this hasn't been too bad!" After crossing the Mt. Ascutney Parkway the trail remained flat for a bit as it side-hilled a ravine/bowl/cirque situation. I caught glimpses over the trees to the summit ridge, which still looked plenty high up! At this point, I decided I'd make a semi-loop of this hike and follow the road down. I passed a toat, and started to steeply climb (calf steep).

I appreciated the wide trail and consequently the lack of spider webs as I suffered my way up. I crossed a couple streams and continued to suffer uphill with some muddy footing, which made sense considering the massive amounts of rain Vermont has gotten recently (plus a tornado?!) - it could have been much worse! Even if the road was longer, it would take me significantly less time because I'd be able to cruise on down.

The Futures Trail climbed again, flattened again, and crossed some streams again in a cool little box canyon-esc spot (followed by more streams, naturally). To my delight, the Steam Donkey spur trail was just after!

[8:25am - Steam Donkey Spur]

The Steam Donkey spur path was less-traveled, but super clear and easy to follow. After just a minute, I landed at the Steam Donkey in question! A sign at the upper parking lot read:

"The STEAM DONKEY is part of our history

Mount Ascutney was logged in the early 1900s. How were the trees removed on such a steep hillside? A STEAM DONKEY is a wooden sled with a steam-enging powered winch and cable system. You can visit the remains of this one, which was abandoned here."

It was a massive piece of rusted machinery with gears and the works. You can tell it's been there for a while, too, because of the plants growing around and inside of it. It also felt very much in the middle of nowhere. I'm sure 100 years ago there were a lot more logging roads, though. Okay, back to exercising.

[8:33am - Futures Trail]

I got back onto the Futures Trail and conitnued onward. The trail was now more wet and rugged, almost feeling like people hike to the Steam Donkey and turn around, which seems silly. My legs were feeling it on this next climb! I think part of it is because my 32-liter pack fits me better than the 40 I'd been weating so the pack weight was now being correctly distributed. I followed a nice walking break and then climbed again to the junction with Futures Link.

[8:45am - Futures Trail/Futures Link]

Here, I decided to continue on the Futures Trail just to satisfy hitting the whole trail in one shot - I'll revisit Futures Link when I hike the Windsor Trail in the future. The trail after the Futures Link junction remained relatively flat, but even less traveled than before. It traversed a few areas of dense ferns, which was fun to see. I did feel myself missing the flowers of early spring, though!

The trail eventually did become more rugged as it climbed up to it's terminus. I also forgot about my new cartiladge piercing and swiped some sweat off of my ear... ouch!

[8:56am - Windsor Trail]

I soon landed on the Windsor Trail, only 0.5 from the top! This trail was MUCH wider and more traveled. The forest in this area was also super pretty with basically everything covered in moss. The Windsor Trail wiggled up the shoulder of Mt. Ascutney, passing some flowering bunchberry, soon arriving at the Castle Rock Trial junction.

[9:03am - Windsor Trail/Castle Rock Trail]

[9:03am - Windsor Trail & Brownsville Trail]

The Castle Rock Trail junction is in such a cool stretch of forest, I think I described it as "primeval" the last time I hiked here, and I maintain! Just after was the junction with the Brownsville Trail, and then the Windsor Trail and Brownsville Trail turned left to finish the climb up the mountain. There were some wonderful boards to walk over. The sky was cloudy, but the mountain was not in the clouds, which was a win!

[9:08am - Brownsville Rock Spur]

I took photos of all three discs at the stone hut remains and hiked along the very wet Brownsville Rock Spur, revealing a beautiful view. Killington and Pico were deep into a cloud, but the valley and Okemo were looking sunny and wonderful! I also found a summit bolt, kind of like the ones in the Northern Presidentials. 

[9:13am - Windsor Trail & Brownsville Trail]

I returned to the Windsor Trail and my way slightly uphill on the comically wet trail. At the junction with the Slab/Slot Trails, there was an adorable red squirrel who was just a bit camera shy. 

[9:18am - Observation Tower]

I climbed up the tower, which had some whipping winds! It felt cold on my soaked shirt. The view from the tower underwhelms me for some reason. I did enjoy seeing Monadnock (in hindsight, it was likely Kearsarge) from the top! The communication towers at the main summit sounded like airplanes from the wind!

[9:23am - Mt. Ascutney Summit]

I made my way over to the main summit, found the two discs, and poked around just in case there was anything more to see, but nope! I did see what I think was a vole scurry around, though! It moved too quickly for a photo.

[9:29am - Observation Tower/Windsor & Brownsville Trail]

Once I was satisfied (and chilly), I hiked back towards the Observation Tower and then the Windsor & Brownsville Trails, hiking past some well-tempered squirrels in the process. At the next junction, I was excited to turn right to check out a new one!

[9:31am - Slot/Slab Trail]

[9:33am - Slot Trail]

I followed the signs for the Slot/Slab Trails (blazed in yellow), which coincided for a minute over flat, wet ground. Soon, the Slot trail diverged left, which I followed (slab sounded too slippery for my liking with how wet everything was). The trail was short, but cool! It skirted the bottom of a large rock wall, almost as if I was traversing in a... slot!

[9:35am - Castle Rock Trail]

[9:39am - Castle Rock Trail/Futures Link]

This terminated at the Castle Rock Trail, with I turned right onto and descended along wet, well-constructed stone stairs. I was finally catching spider webs and the sun was starting to come out! After a few minutes, the trail continued straight while the Futures Link started on the left and the Slab Trail joined on the right. There were two people heading up the Slab Trail - I just missed them! Does this still count as a no-people hike?

[9:44am - Parking Lot Spur]

I found myself really not wanting to do the road walk, but I wanted to think about footing even less, so I continued onward, soon crossing a power cut and then turning left onto the Parking Lot Spur trail. I then crossed paths with a couple and their unleashed dog lear the parking lot. 

[9:47am - Parking Lot]

There were three cars at the parking lot, which explained the people I ran into. There was a big display about bats at the parking lot kiosk:

"MOUNTAIN BATS

TRUE OR FALSE: MOST BATS DRINK BLOOD

     FALSE: Only 3 out of 1,400+ species of bats drink blood, and none of them live in the US.

TRUE OR FALSE: BATS CARRY RABIES

     FALSE: Less than 1% of bats carry rabies.

TRUE OR FALSE: BATS ARE BLIND

     FALSE: Bats have eyesight about as good as humans do, and they can echolocate (use sound to find food).

TRUE OR FALSE: BATS MAKE NESTS

     FALSE: Bats live in trees, caves, bridges, or buildings, but do not build nests.

TRUE OR FALSE: BATS HELP PROTECT WALNUTS, TOMATOES, PEPPERS, COTTON, CORN AND STRAWBERRIES FROM INSECT PESTS

     TRUE: Believe it or not, many of the foods found on grocery store shelves and in kitchen pantries are protected by our bats.

BATS CAN EAT ROUGHLY 1000 MOSQUITO-SIZED INSECTS IN AN HOUR. They can fly up to 60 miles per hour, or more!

A NURSING MOTHER BAT CAN EAT UP TO 4,500 INSECTS IN A NIGHT. Bats can live 30 years!

WHY DO BATS HANG UPSIDE DOWN? Bats cannot take off from the ground, they need to drop from being flying (like a hang glider!). Hanging also helps keep them safe from predators.

THERE ARE NINE SPECIES OF BATS THAT LIVE IN VERMONY. EIGHT OF THEM LIVE ON MOUNT ASCUTNEY. Three are migratory tree bats that raise their babies in trees and migrate south in the winter. The remaining six species are cave bats that hibernate in caves during the winter. Five of these six cave bats are either threatened or endangered in Vermont and federally."

I get they're important, but no bats for me! I stopped for a Nalgene swap and a protein bar at a picnic table overlooking Kearsarge, and then began my descent!

[9:52am - South Summit road]

Just kidding! I saw the access road to the South Summit and decided "it doesn't say not to... so why not!" The road was gravel, lined with flowers, and short. The communication towers were HOWLING in the wind, just like the ones on the main summit. Soon enough, I was there!

[9:54am - Mount Ascutney South Summit]

It really felt like I wasn't supposed to be there, but there were no signs saying otherwise! The main tower was the Vermont Public Television tower, which was fun to see. I wandered around, noticing three distinct straight-line cuts radiating away from the towers, but all were grown-in and did not seem worth exploring. 

[9:58am - South Summit road]

[9:59am - Mt. Ascutney Parkway]

I started my walk back to the parkway, enjoying the tree-view to Mt. Ascutney proper. Soon enough I was back on the Mt. Ascutney Parkway, and down I went! I wouldn't call the trip to the south summit a worthwhile trip, but I'm glad I did it once!

A car passed me heading up and it smelled like it was having a heck of a time. I couldn't help but wonder if people ski the road? There was a decently long flat section after the first descent that might not be too much fun, but the rest of the road seemed like it could be fun! I got catcalled by a red squirrel just before the seven mile mark. I passed time by playing Pokemon Go, which was actually made for a wonderful downhill walk, even if it got steep at times (particularly around curves). 

A Porsche SUV drove up past me a while later and also had quite a smell, and a Tesla soon after, which did not have a smell (tragic). The road descended back into the land of taller, deciduous trees, crossing a bunch of small streams on culverts before crossing the Futures Trail and a larger stream just after. Two more cars drove up the road and one drove down past me as I hiked past a series of cute cabins before I landed at the gravel area from before, which was a parking area for these spooky restrooms and a cool picnic area!

[10:34am - Picnic Spur]

I first checked out the restroom area, which was unlocked but spider-webbed shut, so I peed behind the building. Just a bit further down the road was a mossy sput to a picnic area, which was absolutely lovely. There were seemingly endless CCC-style grills, a medium sized pavillion with a slightly grown-in view. There were more grills and picnic benches seemingly hidden in the woods throughout the area. I took over the Pokemon Go gym at the picnic area (my Gyrados is still there 11 days later), and made my way back to the Mt. Ascutney Parkway.

[10:39am - Mt. Ascutney Parkway]

The rest of my walk down the parkway was pretty uneventful, which was nice. Car #4 was heading upward at a glacial pace. The bugs were starting to become more annoying down low, but nothing a few swats couldn't help. I could soon hear a stream, and soon the stream was down on the right. It was super pretty!

A truck from Florida ZOOMED past me and then a large van was working it's way up. I noticed some logging on the left, and soon after was the gate! I really did enjoy the mindlessness and ease of the road walk, but my feet were barking. I turned right, and soon made it back to my car!

[11:16am - End of Hike]

After my hike I continued my drive up to Vermont and to see Emma's new place! We were supposed to go to soccer game that night, but the rain deterred us. We were planning on hiking the Long Trail from VT-242 to Canada, but it's going to rain all day tomorrow. Ugh. 

Step-by-Step

- Park at campground at Mt. Ascutney State Park.

- Start hike following campground road toward Futures Trail.

- Enter woods at Futures Trail trailhead.

- At jct., turn left onto Bare Rock Vista, then turn around and continue on Futures Trail.

- At road, cross Mt. Ascutney Parkway and continue on Futures Trail.

- At jct., turn right onto Steam Donkey Spur, then turn around and continue on Futures Trail.

- At terminus, turn left onto Windsor Trail.

- Follow Windsor Trail to summit of Mt. Ascutney.

- Follow yellow blazes and Slot Trail down.

- At terminus of Slot Trail, turn right and hike to parking lot.

- Follow Mt. Ascutney Parkway Down, hiking the Picnic Spur on the way.

Map of Mt. Ascutney State Park

Photo Album

Eliot Path, Skyline to Hancock, Jeffries, Dalton, Raccoon Hollow (Blue Hills Reservation)

Eliot Path, Skyline to Hancock, Jeffries, Dalton, Raccoon Hollow (Blue Hills Reservation)

Hike Type: Criss-crossing Loop

Distance: 5.79 miles

Elevation: 1,145 feet

My Time: 2 hours

Book Time: 3 hours, 28 minutes

Parking: Ample parking at Trailside Museum
Hiking Challenges: Great Blue Hill Summits, Trail Trace the Blue Hills 2

The Hike 

I was feeling absolutely desperate for a redemption after yesterday's unpleasant hike. I decided to head down to the Blue Hills after my second to last Monday of the school year to hopefully get what I needed! The drive, naturally, had "heavier than usual traffic," and I was at the trailhead just before 3:40pm. I wasn't feeling like doing a Skyline Loop, so I figured I'd start on the Eliot Path and see where the wind took me. It was 81 and partly cloudy with an intermittent breeze, but the humidity was low and it was NICE. I guess summer can be okay?

The rocks on Eliot Path had a solid dusting of pollen on them, which made them slippery. I made my way up, visiting the ski spur before crossing the Summit Road. The ski trails were grown-in, so I cut through the woods to get both forks of the spur, hiking over many, MANY deer prints all around! I crossed the road and heard the first cicada of summer!

Just before Eliot Circle, I passed a woman in floral skinny jeans with a vastly different floral blouse on. She was actually super friendly, and told me about a family of deer she saw up here a few days ago, implying this floral-on-floral hiking fit was 100% on purpose - spectaular!

I played a little bit of Pokemon Go on Eliot Circle, and followed it all the way to the gravel path to the summit (counter clockwise). The area closest to the ski area was growing in, but by no means overgrown (yet). I worked my way up to the summit, potentially seeing a new gray bird (Update Pending)?

From the summit, I crossed the road and noticed a little path to a parking area, and then another path with a "no bike" plackard by DCR, so I decided to follow it! It was actually a wide, well-beaten path to the backside of the Eliot Tower pavillion - fun! I decided I'd hike the Skyline North to Hancock Hill, hit the Circle Trail, and then see what would happen after that. It was a beautiful day, and I was feeling good!

I made my way down to Wildcat Notch and found a DCR officer in an ATV looking lost or stuck on Puddle Path? She was on the phone with someone holding a map, and then slowly backed out... I wonder where she was heading? I crossed paths with a a family on Wolcott Hill that looked dressed for Houghton's Pond. 

The berries of all sorts were starting to grow in on Wolcott and there was more of that wonderful breeze. I was sweaty for sure, but I did NOT want to die, which was huge! As I descended into Downtown Crossing, I heard the ATV driving away again...

I worked my way up Hemenway, passing a cool snake shed on some of the rocks. I continued along, climbing up after Breakneck Ledge Path and then snaking my way through another family that was coming down towards Circle Trail. 

Up on Hancock's ridge, I noticed some of the blueberriers were starting to turn purple, and some even blue!! I hit the circle of the Circle Trail, which was a little grown-in, but I had my first handful of ripe blueberries of the season! Maybe summer isn't as awful after all...

I continued back into the woods on Circle Trail, enjoying more of a breeze as I made my way down towrads JeffriesTrail. I noticed some horse poop, which must have been a mistake becuase Circle Trail is a horse dead-end. The stream to Jeffries was absolutely bone dry, and higher up, the blueberries were still green. Good to know - Hancock's will be ripe by next week, but Jeffries' are probbaly another week behind. 

I made my way back up Hemenway Hill, and then I descended again on Hemenway Hill Path before hiking on the absolutely delightful Five Corners Path back to Downtown Crossing. I think I traditionally hike this stretch in spring during the melting season, so I've only ever been miserable on this stretch, so this was a win!

I hiked on the Skyline Trail back up Wolcott, trying to pick up the pace because the family was right behind me, and then I went down Dalton Path to get some more new trails. There are some bore holes on rocks near a swamp on Dalton, I wonder what that's all about? I guess either science or an old settlement, but this just feels like a strange place for it.

I hiked up Raccon Hollow, swatting away the only relentless bugs of the day, and then hiked the rest of Eliot Circle to finish out my second summit! I followed the road for a bit to play a little more pokemon, and then made my final descend on Eliot Path back to the car. This was the hike I absolutely needed!

Step-by-Step

- Park at Trailside Museum.

- Start hike on Eliot Path.

- Before road, turn right to ski area spurs.

- Return to Eliot Path at 1051.

- At 1055, turn right onto Eliot Circle.

- After 1030, turn left onto gravel path to summit.

- From summit, continue onto Summit Road.

- At path, turn right.

- Walk across parking lot, continuing onto unmapped path in woods (marked by a no-bike DCR plackard).

- At terminus, walk through Eliot Tower towards 1063.

- At 1063, turn left onto Skyline Trail North.

- After summiting Hancock Hill, hike the circle of Circle Trail clockwise, then continue on Cirlce Trail towards 1180.

- At 1180, continue onto Breakneck Ledge Path.

- At 1185, turn left onto Base Path.

- At 1182, turn left onto Jeffries trail.

- At 1150, turn around.

- At 1154, turn left onto Hemenway Hill Path.

- At 1140, turn left onto Five Corners Path (green).

- At 1141, turn right onot Skyline Trail.

- At 1117, turn right onto Dalton Path.

- At terminus, turn left onto Wildcat Notch Path.

- At 1092, turn right onto Raccoon Hollow Path.

- At terminus, turn left onto Eliot Circle.

- Before 1030, turn right onto gravel path to summit.

- From summit, continue onto Summit Road.

- Follow Summit Road.

- At 1051, turn left onto Eliot Path.

- Return to car.

Blue Hills Reservation Map

Photo Album

Round Hill via School Mountain Road (Fahnestock State Park)

Round Hill via School Mountain Road (Fahnestock State Park)

Hike Type: Lollipop Loop

Distance: 4.61 miles

Elevation: 712 feet

My Time: 1 hour, 39 minutes

Book Time: 2 hours, 39 minutes

Parking: Plenty roadside parking at School Mountain Trail trailhead.
Hiking Challenges: 52 Hike Challenge 2026, Downstate 28er

The Hike 

I was in New Jersey/PA for the weekend to celebrate my cousin's wedding and I wanted to find a stopping point on the way home to break up the drive. I could have done a Catskill High Peak, but I didn't want to go that far out of the way on a Sunday, and then I remembered the Downstate 28er list (which appears to be by the same folks who made the Taconic 12er!). I looked at the hikes that were furthest from Mom's house and landed on two in Fahnestock State Park. The plan was do to hike Round Hill and Candlewood Hill before launching myself back to Boston. I had a nice drive, a little over an hour long from our breakfast spot in Towaco to the School Mountain Road trailhead, which was a long dirt road with plenty of pull-offs and a parking lot (with a porta potty!) a bit further down. It was a humid, sunny 82 degrees when I arrived. I put on my new hiking clothes from Target (underwear that I feared was too short for my thighs, new 7" inseam shorts that I feared would be too soft and absorbent, and a new "active" shirt that I feared would be too heavy and absorbent. Starting off strong!

I started my hike on School Mountain Road, which was an old gated gravel road that was delightfully flat. I was planning to avoid bug spray for as long as possible, if that would be possible. I was excited to see that the trail markers were the Taconic Region ones, for no reason besides a little teehee. 

A minute or so into the hike, there was a kiosk with a map for the Hubbard Perkins Trail, which partly coincides with this and other trails in the park. There was a wonderful floral smell in this area. I soon caught up to a man and his off-leash dog at a sign that specifically detailed why it is important to leash your dogs... I passed him, gave a "how's it going," and got zero response. Yikes!

The School Mountain Road trail crossed over a couple lovely bridges and then I crossed paths with another duo. They were both friendly, and the one ahead shouted "oh shit John! Hurry! You can see a bass!" which made me giggle. The trail continued into the woods with a very easy gain, passing old stone walls and eventually crossing a larger bridge. Just after the bridge was the turn I would take for the blue-blazed Fahnestock Trail up to Round Hill!

Right around here, specifically at the 0.4 mile mark, 9 minutes into my hike, my camera battery died! I was incredibly displeased with this. I hate doing phone-photo hikes. I also just don't like being on my phone more than I need to on hikes, besides taking notes. And I only like taking notes becuase it helps me relive my hikes with more detail when I journal them, like this! Either way, I continued onto the Fahnestock Trail, turning sharply to follow the stream back toward the meadow and the bridges from before. There were a large number of dragonflies that had a teal/metallic thin body and black wings (a very specific google search looks like they were ebony jewelwings, also known as black winged damselflies).

The bugs started to increase, but I just kept my pace up, really avoiding the Deet. The trail stayed flat for a bit, eventually turning away from the water at another old stone wall. After the turn, the trail began to easily rise around the base of Round Hill.

As the vegetation increased, I eventually gave up and coated myself in bug spray, and it was a good thing I did! The trail became pretty overgrown and generally unpleasant to hike through. After rounding the corner, the trail began to start a moderate climb up the spine of the hill, switchbacking here and there with an overwhelming floral smell (which would have been lovely any other day, but not in the humid huff-and-puff). 

I hiked over what I'm pretty sure was a wild cockroach (?) as I was actively dripping pollen-soaked sweat. The baby blubes were taking shape, at least! There was a slightly overgrown view towards Bear Mountain, which was nice to see! I also passed a neat orchid-looking flower (a Goat's Rue, thank's Seek!). As the grassy climb continued, I found myself feeling less excited about getting in the car to get another hike in, so maybe I'll just extend this one? We'll see.

After rounding the shoulder of the hill, the trail worked through a pretty open-ish area that was ridiculously grassly (a la Harriman State Park's Long Path). I had to bug spray my upper thighs becuase the grass was so high. There were some tree views to the left as the trail crossed another old stone wall, and then I had to fight my way through a few thickets of raspberries (or blackberries, or wineberries... either way, thorns!). The grass got so thick at points that I couldn't even see my feet. I was not emotionally prepped for this hike.

I was quickly losing steam to extend the hike along the ridge, especially if this grass kept up. Naturally, after I had that thought, I crossed another stone wall and the grass became waist high. The trail slightly descended before the final climb up. I wrote: "I rarely actively hate a hike but this is really trying for it."

There was a short steep climb before hitting some more grass. Thankfully, the trail flattened at some blueberry bushes before turning for the final push. There were some obstructed views before a wonderful view, where I encountered my first person in a while, going in the opposite direction. 

The Fahnestock Trail rounded the height of land. I took a spur/herd path to the true summit, which was marked by a fire ring and a makeshift cairn. Back on the main trail, I noticed a view out to a nearby hill with a massive observation tower-looking thing. There was a WONDERFUL breeze here as I entered more and more grasslands. There were at least nice pink flowers (carolina roses, thank you, Seek!). 

The trail descended into a low point and then rose just a few feet to the junction with the green-blazed Round Hill Bypass, which I HAPPILY took. At this point, I was pretty sure I was just going to do this hike as-planned and call it a day. I was NOT in the mood and I was already overheated - I'm not ready for full summer. 

This trail was MUCH more enjoyable. It easily descended with rocky footing into a fern-filled wonderland, and I could see my feet the whole time! Further down, I crossed a stream with an adorable frog swimming about and then hiked over another stone wall.

The trail then entered a really pretty open forest with stone walls in every which direction and a vast carpet of green undergrowth (only a few inches tall, which was so much nicer than the multi-foot tall grasses from before. I could tell this used to be farmland clearly, but curious how long ago? The park was opened about 100 years ago. I was missing my camera - it was so pretty!

The trail then turned and rose above a mossy stream that would be absolutely stunning after a rainfall. There was a parent and child playing in the water. The Round Mountain Bypass trail terminated just a couple minutes later at another nice bridge!

The bridge was designed by the West Point Cadets Civil Engineering Class of 2021. I thought about adding a loop over East Mountain, but the trail looked similarly horribly grassy - no thanks! I was back on School Mountain Road and happily hiking back to the car.

I crossed another bridge, this time designed by the West Point Cadets Civil Engineering Class of 2020. I spooked a snake that I thankfully did not see and continued my romp along the beautiful road. I unfortunately was in a slightly negative headspace, so I was not able to fully enjoy the back end of this hike, but it really was lovely. There were seemingly endless stone walls throughout. 

The next bridge was a longer one with wooden steps to reach it, and it was also designed by the West Point Cadets Civil Engineering, this time the Class of 2019. I passed another sightless snake and enjoyed the tall trees lining this trail. After a bit of walking, I officially closed the lollipop and hiked over the final three bridges (I forgot to check if the design pattern continued, but the styles of the bridges sure did match!).

I soon made it back to my car and started to wipe the sweat (and pollen) off and change my clothes. Comically, I realized my backpack had been open the whole time! I did not have the energy in me to squeeze another possibly unpleasant hike in, so it was now time for a long drive back to Boston, naturally with a stop at Stewarts on the way!

Step-by-Step

- Start hike on School Mountain Road (white).

- At jct., turn sharply right onto Fahnestock Trail (blue).

- At jct., turn left onto Round Hill Bypass (green).

- At terminus, turn left onto School Mountain Road (white).

- Return to car.

Fahnestock State Park Map

Photo Album

Skyline Trail Loop via Wright's Hill Trail (Middlesex Fells Reservation)

Skyline Trail Loop via Wright's Hill Trail (Middlesex Fells Reservation)

Hike Type: Lollipop Loop

Distance: 8.18 miles

Elevation: 1,089 feet

My Time: 2 hours, 48 minutes

Book Time: 4 hours, 38 minutes

Parking: Parking for ~15 cars at Bellevue Pond.
Hiking Challenges: 52 Hike Challenge 2026, Middlesex Fells Skyline Trail, Operation Alaska Benchmark Challenge

The Hike 

The end of the school year has been mentally beating the life out of me, so I decided it was time to physically beat myself up too and revist the Middlesex Fells Skyline Trail. I hiked the loop once before, but I did missed the final segment coming down from Wright's Tower, so I guess I had never officially hiked it all. Plus, I found a patch for it on Ebay! It seems to be an older Boy Scout patch, but it still counts! It was warm out in the low 80s.

Bellevue Pond had become mostly a grassy meadow now with just a very small pool of water in the back. I hiked in and decided to take the Wright's Tower Trail first to access the Skyline Trail for views and a little bonus elevation. This was also the pollen-iest day of the year - I was already coated in the yellow toxins. The sunny part of the trail was HOT. The shade was okay. I made my way up and ran into a bunch of teens, so I took my picture at the view and blasted off! I liked seeing the view of Boston in it's new green foliage.

Now officially on my loop, I admired how shaded the woods were. As I climbed up and over the first little knob after D6-2, I passed some baby blueberries. I had to really pay attention to blazes since there are so many criss-crossing paths in the Fells, many of which are not even on thge map. I passed a very stinky duo, which was crazy, because usually I'm the stinky one!

I worked my way up and over the Panther Caves and then passed a bone-dry swamp just after. I took a swig of my warm Nalgene and hit the junction with the Cross-Fells Trail right at the first mile marker. It was fun to hike in this area, it felt a bit like Memory Lane! There was a little swamp before C5-1 and the first of many confusing junctions - which is always my beef with the Middlesex Fells - blazing is either aggressively abundant or severely lacking, and there is simply no in-between.

The Skyline Trail paralleled the Mountain Bike Loop in a swampy area and then joined on a gravel path, then passing a concrete water tank(?) and a stone block in the ground that might mark the town line btween Winchester and Medford, even though it didn't exactly match the map. I descended to West Dam Road, which had a small wetland with a very shy turtle. There were a few annoying bugs buzzing about, but not enough to warrant bug spray.

The trifecta of the Skyline Trail, Reservoir Trail, and Mountain Bike Loop coincided and rose steadily on a gravel path after crossing West Dam Road, and later Skyline and Reservoir veered left away from a metal water tower, splitting from each other a minute or so later. I could feel the pollen granules in my eyes and a large amount of spider webs on my skin. 

I was enjoying this western portion of the loop becuase I had hiked most of it previously in winter, so I really wasn't recognizing most of it! I was also atonished how in the right lighting I could see how thick the pollen was in the air. I climbed up and down another knob to cross Molly Spring Road, and I could hear an owl when I was working my way up and over Nanepashimet Hill, which was SUPER sunny.

There was an old metal beam and rock harlqeuin flowers on the knob after B3-12, and then I had to maneuver a few blowdowns before B3-6. I passed a big cloud of what smelled to be the Devil's Lettuce, but the source was unknown. I could start to see the reservoir though the trees, which was exciting!

I've always been confused about the roads around the reservoir. It seems the roads circling the North Reservoir are open, and were signed as such, even though they're resitricted on the map. I crossed paths with a wild amount of shirtless trail runners in running vests in this stretch, which had really pretty flat pine-y woods.

As I hiked along Hillcrest Parkway, I admired some of the massive hydrangeas in peoples' yards. There is also a good amount of roadside parking here, which was good to know. I hiked past the North Reservoir's dam, which is closed to the public, and I eavesdropped on a duo's gossip session about a friend who inherited a bunch of money recently, it was a very fun 10 seconds!

The Skyline Trail goes back into the woods and zig-zags down to the reservoir's outflow stream, which was just a trickle. I crossed the creek on a NEMBA bridge, enjoyed a nice breeze, and began to make my way towards the Bear Hill Area, which was still pretty foreign to me. 

I almost got lost at C1-4 due to an unsigned and unblazed turn, but thankfully my brain thought "this feels wrong." The trail hit a low point just after with some rotting bog bridges just before rising to the Dike Road.

I climbed up the side of Bear Hill, passing an older hiker and his well-behaved and possibly overheating golden retriever and after the height-of-land, the trail became full of a wonderful, floral scent with no flowers to be seen!

As I approached the Sheepfold area, the Skyline Trail became more of an open trail, crossing knob after knob, many of which were open, and they were HOT. Winthrop Hill had a sunny bench overlooking some grasses at the top, and I almost got lost again at D3-1.

I maneuvered around an impressive blowdown just after C2-8 and then skimmed the outside perimeter of the Sheepfold area next to a swamp. There seemed to be a good amount of folks out at the main Sheepfold area, but the Skyline Trail was still full of spiderwebs! I was happy to be in the shade, though.

The Skyline Trail briefly followed a paved path as I-93 roared in the distance. The trail cut through a parking area, crossing a couple of paved single-land roads, and then turned left onto a nice boardwalk. I noticed a bit of a hot spot on both of my big toes and right heel, but naturally decided to avoid it. I felt myself finally starting to tire out around the six-mile park, but I kept on moving!

I joined the Cross-Fells Trail again and almost got lost... again soon after. The Cross-Fells left soon after joining and I officially finished all my water (only 1L, oops) on Silver Mine Hill. It was hotter than I was ready for! I joined the Cross-Fells yet again at C5-18 and crossed paths with a trail running trio I saw over by the North Reservoir - only this time they were power hiking. The two guys were leading and the woman was suffering behind, I felt kind of bad for her.

I finally made it to my final push up to Pine Hill and I was tired! Eight miles after school in the heat took more out of me than I was ready for! I decided to look for all three discs again: I found the northernmost one, an arrow, and it was pointing to a summit disc. But... I don't think I'd seen this one before? On a higher rock to the east was another arrow, which I think I had seen before. Wait this is three? I already knew about the magnetic station, so there's four up here? I worked my way over, and found ANOTHER arrow?! Five discs?! This was beyond exhillerating to me and fully brought me back to life. 

Riding the high of discovery, I continued onto the tower and was SHOCKED to see how insane the pollen haze had become - it was so thick I couldn't even see the Blue Hills! 

From here, I descended back along the yellow trail and made it back to the car, dusting myself off before driving back home. Another patch "earned"!

Step-by-Step

- Start hike on Quarry Road.

- At jct., turn right onto Wright's Tower Trail (yellow).

- At tower, turn left onto Skyline Trail (white).

- Follow Skyline Trail clockwise around, back to tower.

- At tower, descent via Wright's Tower Trail (yellow).

- At terminus, turn left onto Quarry Road and return to car.

Middlesex Fells Reservation Map

Photo Album

Chickatawbut Hill, Bouncing Brook Path, Skyline Trail Loop (Blue Hills Reservation)

Chickatawbut Hill, Bouncing Brook Path, Skyline Trail Loop (Blue Hills Reservation)

Hike Type: Mostly Lollipop Loop

Distance: 4.54 miles

Elevation: 640 feet

My Time: 1 hour, 39 minutes

Book Time: 2 hour, 35 minutes

Parking: Room for 20-30 cars at Chickatawbut Overlook.
Hiking Challenges: 52 Hike Challenge 2026, Trail Trace the Blue Hills 2, Blue Hills Grid

The Hike 

I made my way back to the Blue Hills after school, suffering through another afternoon of "unusually heavy traffic." The inspiration for this hike was the Blue Hills Grid that I've been "working" on for years now, plus my second Trail Trace map. I had field day today, so I had been outside for a lot of the afternoon, but I was excited to keep the momentum going! It was 78 degrees out and overall pretty pleasant!

I made my way into the woods and up to the tower before following the yellow blazes counter-clockwise. I stopped for a quick potty break and managed to pee on my hip belt strap... Ugh. I worked my way up Thayer Path, which was grassy up around the summit fence (I had tick anxiety). I went down Carve Path, which had it's trademark giant rock piles that I've always been wildly curious about. 

I then made my way down onto the Bouncing Brook Path, which I'd be following for a while. It was darker and more humid down there, and I was following horse prints for most of the walk. I passed some lovely purple flowers, which were lesser periwinkle, not violets. I passed a really nice stone wall I hadn't noticed before just before the junction with Lee Path, and then a lady slipper just before the junction with Sassaman! Just kidding! At the junction with Curve Path! I missed a turn! That's fine, my hike was going to be a bit longer.

Everytime I'm hiking these interior Chickatawbut trails I'm reminded of how long they feel - it must be because there's a thinner density of trails in this area, or something. The bugs were present but not much of a bother as long as I kept on moving. I worked up Wampatuck Path and then the Pocapawmet Path to join the Skyline Trail!

I don't think I have traveled this direction on the Skyline Trail since a hike with Gen and Wylie in the winter of 2021 or 2022 - it's been a minute! I passed a super cute eastern towhee on my way up Broken Hill #4 and then maneuvered the rockiness that surrounds #3 - there were baby blueberries! A deer magically lept across the trail as I was climbing up #2 and there were some young rock harlequin flowers at the top. 

The climb up #1.5 was also rockier than I had realized traveling in the other direction, and I found myself wondering how different the forest would be on #1 in 10, 20, 50 years since the last fire. It looked like most of the pines were dead/dying and the undergrowth was growing in strong! I passed more pink lady slippers and rock harlqeuins as I descended #1, and then I started my climb up Nahanton.

The climb up the Chickatawbut Ridge was actually more gradual than I was emotionally ready for. I climbed on up Nahanton, past some more baby blubes, and found myself wondering yet again about the old foundation-like things. I admired the stone steps up Kitchamakin and suffered through the brush to reach the true top of Fenno Hill before making my way up to Chickatawut Hill. I descended via Stowe Path and made it back to the car - this was officially a zero-person hike! I dusted the pollen off of myself (literally) and heard a barrel owl calling somewhere on the other side of the road.

Step-by-Step

- Park at Chickatawbut Overlook.

- Start hike on Tower Path (yellow).

- At 3075, turn left onto Sassaman Notch Path (yellow).

- At second jct., turn right onto Thayer Path.

- At fence, turn left.

- At second jct., continue right onto Skyline Trail (blue).

- At 3065, turn left onto Carve Path.

- At 3051, turn left onto Bouncing Brook Path (red). 

- At 3152, turn left onto Wampatuck Path.

- At 3171, turn around and turn right onto Pocapawmet Path (unmapped).

- At terminus, turn left onto Skyline Trail (blue).

- At Chickatawbut Hill, turn right onto Thayer Path, then turn right again onto Stowe Path.

- At jct., turn left to stay on Stowe Path.

- At terminus, turn left onto Sassaman Notch Path (yellow).

- At 3075, turn right onto Tower Path (yellow).

- Follow Tower Path back to car.

Blue Hills Reservation Map

Photo Album

Red Dot and Skyline Loops via Trailside Museum (Blue Hills Reservation)

Red Dot and Skyline Loops via Trailside Museum (Blue Hills Reservation)

Hike Type: o-O Loop

Distance: 4.97 miles

Elevation: 1,220 feet

My Time: 1 hour, 46 minutes

Book Time: 3 hours, 5 minutes

Parking: Ample room at Trailside Museum
Hiking Challenges: 52 Hike Challenge 2026, Trail Trace the Blue Hills 2, Great Blue Hill Summits

The Hike 

Happy Pride Month! It was time to officially begin my second Trail Trace the Blue Hills Map! I had a dreadfully sleep drive with "heavier than usual traffic," landing at the Trailside Museum at 3:35. There were very few cars, which brought me joy! I was planning on just doing a fitness hike with a possible detour to get the full red-circle route for my new map, we'll see! It was sunny, 62 degrees, and there was a light breeze. It was lovely!

Somebody unfortuantely got started right before me, but I had to pull off to pee anyway. I eventually caught up and passed him and continued my way up. There were a bunch of leaves on the ground after Saturday's storm. My legs were in a weird mood, feeling a bit like a baby deer learning to walk. I couldn't really get a rhythm together on my climb. Thankfully, I could hear a bunch of eastern towhees, which made it feel better!

I passed a bunch of white daisies after summiting the first time. The work on the summit area has been continuing, with another widening of the Eliot Circle for trucks (I assume). I made my way onto the Skyline Trail North, admiring how shaded it is this time of year. Naturally, I was gassy on this hike, and at one point I made three stomps, farting on each stomp, and the pitches of each fart were different and accurately mimiced the final three notes of the University of Massachusetts Minuteman Marching Band's rendition of Frank Sinatra's My Way - it was remarkable.

I worked my way up and over Wolcott, Hemenway, and then Hancock. My body was just feeling tired and heavy, maybe because I had wine before bed last night? I passed some beautiful blue jays coming down Hancock Hill and I was simply not emotionally ready for the climb up Houghton. Thankfully, the climb did not humble me as badly as I thought it would. I did gas me out, but I was not passing away.

The leaves made the Skyline Trail super dark at the first stream crossing, and to my absolute delight I found some lady slippers between 1123 and the Five Corners Path!! This is where I usually find them this time of year, so I was just elated.

The second stream crossing was fully dried up and I noticed a path straight ahead before the crossing to what looks like a cave? I had never noticed it before... interesting! I made a note of it, being too lazy to investigate. I zig-zagged up to the final headwall, suffered on up, and then continued up along the shoulder for the final push, which always feels longer than I am ready for!

I listened to the northern house wrens at the summit (thank you, Merlin!) and decided to follow the other half of the red loop for my trip down, which was lovely. The swamp along the trail was mostly dry, and it looked like DCR is working on formally closing a few of the abandoned trails in that area. My final stretch of trail was cheered on by a friendly Robin, which was just lovely.

Step-by-Step

- Park at Trailside Museum.

- Start hike on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle.

- At summit road, turn left.

- At jct., turn right.

- At summit, hike around observatory clockwise, following gravel path.

- At terminus of gravel path, turn left onto Skyline Trail (blue).

- At 1063, turn right onto Skyline Trail North.

- At Hillside St., turn right onto Hillside Street.

- At jct.,. turn right onto Skyline Trail South.

- At 1066, turn left onto Eliot Circle/Skyline Trail.

- At gravel path, turn right onto Gravel Path.

- At summit, continue straight and hike spur towards ski trail.

- At jct., turn right onto Eliot Cirlce.

- After 1055, turn left onto Raccoon Hollow Path (red).

- At 1082, turn left onto Cliff Trail (red).

- Cross Summit Road, continue onto Trailside Path (red).

- Follow red dots back to car.

Blue Hills Reservation Map

Photo Album