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

Cross Path, Whip Hill, Crystal Spring Path/Road (Middlesex Fells Reservation)

Cross Path, Whip Hill, Crystal Spring Path/Road (Middlesex Fells Reservation)

Hike Type: Spaghetti Loop

Distance: 3.71 miles

Elevation: 427 feet

Time: 1 hour, 15 minutes

Parking: Ample parking at Greenwood Park in Stoneham.
Hiking Challenges: Middlesex Fells Reservation

The Hike 

I take back every complaint I've made about heat in 2026 (that's a lie), because it was officially HOT. I was getting an after-school hike in at the Fells on a STEAMY 94-degree day. Ouch. To make things worse, the porta potty at Greenwood Park was gone! My goal was to connect the final dots in this area of the Fells, but acknowledged that it was miserable out and wasn't going to push myself too hard. I got suited up and off I went!

I was sweating 50 feet away from my car, and then passed a massive group of hikers (looked like a guided hike) before turning onto Whip Hill Road, which donned a bunch of wonderful flowers! The humidity cranked up whenever the trails paralleled wetlands, which felt... unpleasant.

I continued onto Cross Path, hiked the triangle at F2-8, and then worked my way onto the other Whip Hill trails that don't go over the top. I heard a barred owl through the trees, but sadly didn't see it. There was an interesting man (or alien)-made fence made of fallen limbs going up Whip Hill, and once I was over the other side I had a sip of hot Nuun, which is never pleasant. I meandered around, eventually landing back on the giant split rock at F2-15 before hitting some more new trails.

Whip Hill Park was FULL of blooming mountain laurel, which was just a delight to see. There were also a couple turkeys on the trail that descends to Gate 47 - one was gobbling up a storm and was HUGE. The trail passed a few back yards before hitting the gate, where I turned around to continue my wander.

I passed some robins baithing in a little drainage stream and worked my way on the littles uphill on the Crystal Spring Path, where my nose started to bleed! Yikes. I did a little loop, went uphill again, and then descended to Crystal Spring Road, which was mostly paved and lined with flowers - kind of lovely!

After bouncing around at the parking area off the Lynn Fells Parkway, I landed at Gate 41 and walked along Pond Street to hit my final stretch of trail, which was blazed for the Crystal Spring Trail, which didn't match the map (annoying). I also noticed a wooden rectangular post that said Saddleback Path on it at the road - I wonder if there's more of these throughout the park like at the Blue Hills?

I hiked uphill to the green blazes and to my delight was just about done! I was COOKED. I'm so not ready for summer summer (I AM ready for summer vacation, though). I made it to Christien's and immedaitely took my first cold shower of the season!

Step-by-Step

- Park at Greenwood Park

- Start hike on red-blazed Crystal Springs Trail northbound.

- At E2-1, turn right onto Whip Hill Road (green).

- At F2-3, continue onto Cross Path.

- At F2-8, hike triangle, and then turn left onto Crystal Spring Path.

- At F2-9, turn left onto path.

- At F2-10, hike triangle and then turn right (green).

- At F2-14, turn left.

- At F2-13, turn left.

- At F2-1, continue straight.

- At E2-9, turn left onto Whip Hill Path (green).

- At F2-2, turn left.

- At F2-10, turn left (green).

- At F2-14, turn left.

- At F2-15, turn right (green).

- At F2-16, turn left.

- At F2-17, stay straight (do not enter Whip Hill Path, follow path along homes).

- At Gate 47, turn around.

- At jct., turn left onto Crystal Spring Path.

- Hike spur between F2-20 and F2-19, then continue on Crystal Spring Path.

- At F2-18, turn right.

- At F2-17, turn right.

- At jct., veer right.

- At F2-19, turn right onto Crystal Spring Path.

- At F2-6, turn left onto Crystal Spring Road.

- At Lynn Fells Parkway, turn around.

- At Gate 41, turn right onto Pond Street.

- At jct., turn right onto Saddleback Path.

- At E2-6, turn left (green).

- Follow green blazes back to car.

Middlesex Fells Reservation Map

Photo Album

Crystal Spring Loop, Doleful Pond, Healthy Heart Loop (Middlesex Fells Reservation)

Crystal Spring Loop, Doleful Pond, Healthy Heart Loop (Middlesex Fells Reservation)

Hike Type: Loop w/ spur, Loop, Little Loop

Distance: 5.09 miles

Elevation: 361 feet

Time: 1 hour, 43 minutes

Parking: Ample parking at Greenwood Park in Stoneham.
Hiking Challenges: 52 Hike Challenge 2026; Middlesex Fells Reservation

The Hike 

I foolishly thought yesterday was hot. Today was HOT. 80 degrees! I was killing time while Christien was at work, so I fugred I'd get the trails in the Crystal Spring/Doleful Pond area of the Fells for the first time. Plan was loosely a double loop, first following the red Crystal Spring blazes and second following the green Healthy Heart trail.

The hike started through a really cute loosely zoo-themed playground and then I started to follow the red loop around! The trail passed a meadow restoration area and then followed a small little boardwalk around a swampy area that's drying up. I then broke my plan of following red blazes and hit the spur trail to Doleful Pond, since it was a one-way trail anyway. I was loving how green everything was, but not obsessed with the bugs or being able to feel the pollen. 

At Gate 46, there was a backyard with dozens and dozens of birdhouses. I turned around and hiked to Gate 45, and enjoyed my time along the pond, which was more or less a murky pond that was 50% tall reeds. I did see a great blue heron flying away! There was a viewpoint that had two old stadium seats, which I found interesting. 

Dolefiul Pond Road paralled a stone wall, turned right, and then followed people's back yard fences to the gate. This was a nice side trip! Now, back on task.

There was a nice breeze and I was SWEATY from the hot sun. Back on the Crystal Spring Trail, I climbed up Whip Hill on a more trail-like trail as the treetops were clanking in the breeze. Near the top of the hill, there was a sign discussing rogue trails and what students at Stoneham High School are doing to help, which was cool. I passed a few people, but soon remembered that hikers are NOT nearly as friendly here as they are in the Blue Hills. Thinking about it, I think it's partly because this side of the city runs more metropolitan, and also more people are here for "walking" versus "hiking."

After Whip Hill, the Crystal Spring trail descended slowly all the way to Crystal Spring, which had some cool stone structures and many flowers, including the common blue violet. There was no water flowing, but still cool to see! The trail climbed after this and turns right near the height of land. The forest floor here is dotted with common mayflowers pre-budding, which was really pretty. 

Afterwards, the trail began to gradually climb up Saddleback Hill, which soon had a nice view over the road and to Spot Pond Reservoir. The wind was whipping! Afterwards, there were a couple more partial viewpoints, and then I was back at the playground!

I walked through the playground, which was more full of children this time around, probably because school was out. I started to follow the green blazes for Loop #2, but did hit the extra spur of Whip Hill Road before continuing on. The green blazes brought me around a wetland area and later made a few crossings with the Crystal Spring Trail. It circled an impressive boulder on the far side of the loop, and once near Saddleback Hill I checked the map and managed to get a stick in the eye... ugh...

Anyway, I soon finished that loop, and now it was time to just wander! I turned right at E2-2, hiked in towards some trails I hadn't hiked yet, past a wildly unphased deer, and then got the text that Christien was heading out, so it was time for me to head out, too!

Step-by-Step

Loop #1

- Park at Greenwood Park

- Start hike on red-blazed Crystal Springs Trail, clockwise.

- At E1-2, turn left. 

- At E1-1, turn right onto Doleful Pond Road.

- At Gate 46, turn around.

- At Gate 45, turn around.

- At E1-1, turn right.

- At E1-2, turn left onto Crystal Springs Trail.

- Follow Crystal Springs Trail clockwise, hiking spur to Pond Street, then continuing.

- At E2-3, turn left onto trail.

- At Woodland Road, turn around.

- At E2-3, turn left onto trail.

Loop #2

- Back at Greenwood Park, start hike at same spot, following green Healthy Heart blazes.

- At E2-1, turn left onto Whip Hill Road

- At "NO TRESPASSING," turn around and follow green blazes clockwise. 

- At E2-6, turn left.

- At E2-5, turn around.

- At E2-5, turn left.

Loop #3

- At E2-2, turn right.

- At E2-7, turn right.

- At E2-8, turn left.

- At F2-2, turn around.

- At E2-8, turn right onto Whip Hill Road.

- At E2-1, turn left and return to car.

Middlesex Fells Reservation Map

Photo Album

Northern Fells Reservoir & Virginia Wood Trails (Middlesex Fells Reservation)

Northern Fells Reservoir & Virginia Wood Trails (Middlesex Fells Reservation)

Hike Type: Spaghetti

Distance: 6.73 miles

Elevation: 778 feet

Time: 2 hours, 8 minutes
Hiking Challenges: Middlesex Fells Reservation Redlining

Parking: Pulloff on Pond Street at Gate 42

The Hike 

Now we're really back at work, because I was back at the Fells killing time while Christien finished up work. It was a beautiful 60-degree afternoon with no clouds and a light breeze. My goal was to hike through the Virginia Wood section of trail and possibly finish up the area around the Fells Reservoir. Parking was unpleasant, as it was a small pull-off on a busy road, but ultimately fine. I wish I brought my long sleeve since I was chilly to start, but was soon completely fine. 

In the woods, the undergrowth was starting to sprout! I crossed a neat old bridge on the Crystal Spring Trail, which was blazed in red, and partially coincided with a Historical Trail, which was blazed in yellow. I had to carefully and safely cross Ravine Road, which was busy, and then hiked up a Pipe Line, which was expectedly underwhelming. My windbreaker finally came off since the Pipe Line was on a slight incline, and I didn't realize that I had dropped my phone taking it off! Thankfully, it was only about 50 feet down the trail from when I noticed, but yikes!

There were a few nice woodpeckers near the reservoir as I followed the Wyoming Path, which eventually split and I joined the reservoir, which is really a lovely walk. It reminded me of a mini Quabbin. Some parts of the reservoir were lined with a tarp, which was interesting, but I guess made sense? Maybe those were areas where water was leaking out?

There were a couple of ducks swimming about as I hiked around, high above the land down below. There were a medium amount of unmapped trails around the reservoir, but I was really just planning to stick to what's mapped. I exited the reservoir area eventually and found myself behind a women walking TWELVE dogs?! It looked like a scene out of a movie. Thankfully, she pulled over to let me pass. 

I hiked a hanging chad trail that I needed and met a white bird that I hadn't seen before (a white-breasted nuthatch - thank you, Seek!). I managed to cut my arm on a pricker bush and hiked past a little meadow while on the Rock Circuit Connector, which then zig-zagged around some rogue trails that led back to the reservoir.

I needed a few trails around the Fellsway East and Ravine Road, which unfortunately led to a road walk to save miles. It was sketchy, but thankfully I had enough of a shoulder where itw as mostly fine. I wrapped up the Wyoming Path area and then made my way to the Melrose Path/Pine Grove Path area, which involved a lot of wiggling and zig-zagging and one unpleasant road walk. The Pine Grove was my favorite area around here, as it was true to it's name!

My return trip started back on the Rock Circuit Path to the terminus of the Crystal Spring Path. The sun felt amazing on the open slabs, but it was getting chillier in the woods. I realized I was going to finish the Fells Reservoir area, which was exciting! I followed Crystal Spring Path back to Melrose Path, hopped a few blowdowns, hit a few spurs, and voila! I did it!

Now I had to cross Ravine Road again and decided to go for one last road walk uphill to the Virginia Wood road. I had just enough time to hike the network of trails in this small area of the park, the coolest being the Historic Trail. The only information on this area on the DCR map reads: "Virginia Wood, the site of a vanished mill village called “Haywardville,” is now a hemlock enclave featuring a self-guided interpretive history trail."

Wikipedia's "Spot Pond Archeological District" page reads: "The Spot Pond Archeological District is a historic archaeological site near Spot Pond in Stoneham, Massachusetts. It is located in the Virginia Woods section of the Middlesex Fells Reservation, a state park. The district encompasses sites along Spot Pond Brook that were mill sites dating from the 17th to the 19th centuries. At its height, in the mid-19th century the Hayward Rubber Works was located in the area, giving it the name "Haywardville". One of the park's trails runs through the area, and a park pamphlet provide a self-guided tour joining the major remnants of the industries that once flourished there." I also found a lackluster map here.

I'm sure there's a DCR map somewhere, but I have been unable to find it. The trails got a little confusing, but were fun to explore. I ended my hike with my first gnat in my eye of the year! I finished up this stretch of the park also, which felt good, leaving just the main Crystal Spring area, the Spot Pond Reservoir area, the area around Sheepsfold, and the area northwest of the big reservoir. Almost there!

UPDATE FROM THE FUTURE: I found the brochure I wanted about the guided tour in the Virginia Wood - here.

Step-by-Step

- From parking at Gate 42, follow the middle trail.

- At F3-2, continue straight over bridge, following red/yellow blazes.

- At F3-4, continue straight on Crystal Spring Trail (red).

- Cross Ravine Road, continue on Pipe Line Road after Gate 39.

- At terminus, turn left onto Wyoming Road.

- At jct., turn right to loop Fells Reservoir.

- At jct., turn left.

- At jct., turn left.

- At F5-1, continue straight on Hemlock Pool Road.

- At F5-4, turn left.

- At F5-6, continue straight on Jerry Jingle Road.

- At F5-9, turn sharply right onto road.

- At F5-5, turn right onto Rock Circuit Connector (orange).

- At F4-10, turn left onto trail.

- At F4-11, turn right onto Rock Circuit Trail.

- At jct., turn right onto Rock Circuit Connector (orange).

- At jct., turn left.

- At Fellsway East, turn left onto Fellsway East.

- At Gate 50, turn left onto Wyoming Path.

- After F4-7, turn around.

- At F4-7, turn left onto path.

- At terminus, turn sharply left onto Melrose Path.

- At F4-2, turn left onto Rock Circuit Trail (white).

- At jct., turn left.

- At terminus, turn right onto Melrose Path.

- At jct., turn right.

- At F3-10, continue straight.

- At terminus, turn right onto Ravine Road/Fellsway East.

- At jct., turn right onto Pine Grove Path.

- At F3-8, turn left onto Crystal Spring Trail (red).

- At jct. after F3-9, turn left.

- At terminus, turn right onto Wyoming Path.

- At F4-8, turn right onto Rock Circuit Trail (white).

- At F4-4, turn right onto Crystal Spring Trail (red).

- At F4-3, turn left.

- At terminus, turn right onto Melrose Path.

- At F3-7, turn right onto Pine Grove Path.

- At F3-8, turn around.

- At F3-8, turn right onto Melrose Path.

- At Gate 40, turn around.

- At F3-8, turn right onto Crystal Spring Trail (red).

- At Gate 39, turn left onto Ravine Road.

- At Gate 38, turn right (signed: Virginia Wood).

- At F3-3, turn right onto Crystal Spring Path (red/yellow).

- At F3-4, turn left onto Historic Trail (yellow).

- Hike spur, then turn right at F3-5.

- At F3-6, turn right.

- At terminus, turn around and retrace steps past F3-5.

- At F3-3, turn right.

- At F3-2, turn left to follow red/yellow blazes.

- At F3-1, turn right to parking lot.

- At parking lot, turn around.

- At F3-1, turn right to conitnue loop, following yellow blazes.

- At F3-2, continue straight toward Gate 42.

- At Gate 42, complete hike.

Middlesex Fells Reservation Map

Photo Album

Bellevue Pond, Wright's Tower, Panther Caves, Cross-Fells, Skyline Trail Loop (Middlesex Fells Reservation)

Bellevue Pond, Wright's Tower, Panther Caves, Cross-Fells, Skyline Trail Loop (Middlesex Fells Reservation)

Hike Type: Loopty Loop

Distance: 3.63 miles

Elevation: 554 feet

Time: 2 hours, 1 minute (1 hour, 41 minutes moving)
Hiking Challenges: 52 Hike Challenge 2026

The Hike 

Back to Wright's Tower for the first time in a while! I was meeting up with Kerri, who I hadn't seen in a few weeks (and hadn't hiked with in a couple years!). I was running 15 minutes ahead of her, so I hiked up the tower and around Bellevue Pond first without her, and then we had our grand reunion back in the parking lot (perfect timing!). It was a beautiful afternoon with abundant sunshine and temperatures in the mid-50s and we had no plan besides the tower. I only carried my water bottle with me and we took Wright's Tower Road up to the top and had a nice long sit to catch up - I missed her!

After our sit (aka when I started to get chilly), we started to hike around. She mentioned wanting to visit the Panther Caves and I THOUGHT I knew how to get there (spoiler alert, I guess and I was correct!), so we wiggled there via Mud Road and Red Cross Path. We did a little exploring and then continued onto the Skyline, Cross-Fells, and Skyline Trails again. It was nice to pair the easy old road walking with some more rugged trails. The frogs were doing their jobs nicely, too!

We worked our way back to the tower for one last bit of "ooo"s and "ahhh"s before hiking back to the cars and parting ways - such a nice afternoon!

Step-by-Step

- Park at Bellevue Pond.

- Start hike at Gate 5/Quarry Road.

- After D6-5, turn right onto Wright's Tower Trail.

- At tower, continue onto Wright's Tower Road.

- At terminus, turn left onto Quarry Road.

- At D6-3, turn right.

- At C6-9, turn left.

- Hike along parking lot back to Gate 5.

- Continue onto Quarry Road.

- At jct., turn right onto Wright's Tower Road.

- At tower, turn around. 

- At D6-2, turn right onto Mud Road.

- At C6-3, turn left onto Red Cross Path.

- Explore Panther Cave, then continue northwest on Skyline Trail.

- At C5-16, turn right onto Cross-Fells Trail.

- At C5-18, turn right onto Skyline Trail.

- Follow Skyline Trail back to tower.

- At tower, turn around and follow Wright's Tower Road.

- At terminus, turn left onto Quarry Road.

- Follow Quarry Road back to car.

Middlesex Fells Reservation Map

Photo Album

Jerry Jingle, Cross Fells, & Far Eastern Fells Loop (Middlesex Fells Reservation)

Jerry Jingle, Cross Fells, & Far Eastern Fells Loop (Middlesex Fells Reservation)

Hike Type: Tracing Loop

Distance: 5.31 miles

Elevation: 715 feet

Time: 1 hour, 56 minutes
Hiking Challenges: 52 Hike Challenge 2026, Operation Alaska Benchmark Challenge

The Hike 

The sun was out, I was spending the night in Cambridge, so back to the Fells I went! It was chilly with temperatures in the low 40's, but with a brisk pace a long sleeve and shorts is all I needed. I was hoping to finish up the area south of the Fells Reservoir and then, who knows! I started my hike near F5-3 and hiked towards the delightfully named Jerry Jingle Road, which was a classic old road in the Fells. There were some gravelly spots that I didn't care for, but overall it was smooth sailing. 

I worked my way near Gate 55 and noticed a large piece of granite off in the woods (like the trailhead markers in the Blue Hills), but I don't think I was near a town line, so who knows! I was noticing many more people than I had been recently, which I guess is just another sign of the changing seasons. 

I made my way over to the Cross Fells Trail, which was back to a footpath, passed a weird cage-like thing (maybe to trap a problem animal?) and climbed to the height-of-land, which had an old USGS disc and an obstructed view towards Boston. I THINK this is the last disc in the Fells I hadn't yet found (three near Wright's Tower and one here). 

I crossed the Fellsway East and decided I'd start connecting the dots on this isolated section of the Reservation - I immediately was enjoying seeing the spots I'd hiked on the Rock Circuit Trail from new perspectives! I got a little turned-around at the confusing white blazes (the actual blazes and the marked trail on the map for the Rock Circuit do not fully match around Pinnacle Rock), but I made it around just fine. I found an unmapped spur to a view near Pinnacle/Ziggy's Rock which had a view towards the Back Bay and Great Blue Hill, which was fun. I was also just enjoying how rugged this area is - the glaciers really worked hard here! I could even hear the occasional Wood Frog and Peeper!

I made a little loop around East Path, where I found a couple more unmapped off-trail views toward Melrose and Boston. One view had a collapsed tent and a memorial rock to "Miss Kitty," so I did not stay there long. My nose was feeling a little stuffy, which I think was a sign of allergy season beginning.

I DID find another slab of granite that WAS marking the Melrose/Malden town line, which was fun. I worked my way over towards White Rock Path and all the way towards Fellsway East at Gate 49, which was a quiet, lovely walk. I did smell some smoke on my return trip and heard sirens, but I couldn't see anything from the viewpoints. 

I eventually made it onto the yellow blazes for The Cascade, and the water was flowing beautifully! I'd never seen this area with actual flowing water, so this was a treat! I had a rough descent down the yellow-blazed trail, but the view was worth it. I followed the trail around back towards the Cross-Fells Trail, passed the only person I'd see on this side, climbed up the steep hill, and then made my way back to the car. I was HUNGRY, and happy to be finishing up! I was also just delighted to officially complete this Far Eastern section of the Fells - I didn't think I would, yay! I did leave one hanging chad south of the Fells Reservoir, but that's a problem for another day.

Step-by-Step

- Park near F5-3.

- Start hike on Cross-Fells Trails towards F5-3. 

- At Gate 53, turn around onto Jerry Jingle Road.

- At F5-6, turn right.

- At F5-4, turn left

- Before F5-9, turn right.

- At F5-9, turn right onto Jerry Jingle Road.

- At Gate 55, turn around.

- At F5-9, turn left.

- At F5-1, turn right onto Cross-Fells Trail.

- At Gate 53, cross Fellsway East.

- Continue past Gate 52 onto Cross-Fells Trail.

- At F5-10, turn right.

- At jct., turn left.

- At G5-8, turn around.

- At F5-12, turn right.

- At F5-11, turn right.

- At Fellsway east, turn around.

- At F5-11, turn right onto Pinnacle Path.

- At Gate 56, turn around.

- At F5-11, turn right.

- At F5-12, turn right.

- At G5-9, hike triangle and continue north.

- At G5-6, turn left onto Cross-Fells Trail.

- At G5-4, turn around.

- At G5-7, hike triangle and hike south on East Path.

- At G5-9, turn right.

- At G5-6, turn left on Cross-Fells Trail.

- At G5-7, turn left.

- At G5-3, turn left.

- At G5-1, turn right onto Black Rock Path.

- At G4-3, continue onto White Rock Path.

- At Gate 49, turn around.

- At G4-3, turn right.

- At Gate 51, turn around.

- At G4-3, continue straight.

- At G4-4, follow yellow blazes to The Cascade.

- At Goodyear Ave., continue onto Cross-Fells Trail.

- At G5-3, turn right.

- At G5-1, turn left onto Black Rock Path.

- At G5-4, turn right.

- At Gate 52, cross Fellsway East and return to car.

Middlesex Fells Reservation Map

Photo Album

Hemlock Pool & Middlesex Fells Reservoir Area (Middlesex Fells Reservation)

Hemlock Pool & Middlesex Fells Reservoir Area (Middlesex Fells Reservation)

Hike Type: Tracing Loop

Distance: 4.75 miles

Elevation: 377 feet

Time: 1 hour, 39 minutes
Hiking Challenges: 52 Hike Challenge 2026

The Hike 

Happy St. Patrick's Day! I am convinced that all children are evil leprechauns becuase work was BAD today. I scooted over to the Fells before going to Christien's for a little stomp around. I landed around 3:15pm and temps were in the mid-40s with a chilly breeze but bright sunshine. Plan was to romp around the Rock Circuit Trail corridor hitting as many new trails as I could. I had shorts on with a long sleeve and fleece to start - it was feeling like a fall day!

I crossed Woodland Road and continued onto Woodland Path, which was expectedly wet. I was wishing I had a pair of gloves and my buff, but oh well! I maneuvered around a decent amount of sticks, twigs, branches, and the works after last night's wind storm, and there was a little flooded stretch near the Rock Circuit/E5-2 area, but nothing outrageous. I hiked the Hemlock Pool Path, first to Hemlock Pool, where I heard the beautiful call of Wood Frogs! Two guys were skipping rocks on the pool, which like, fine, but let the frogs croak in peace!

I took off my fleece and hiked towards Gate 53 and a little spur trail along a stream which REALLY smelled like spring (which I concluded is simply the smell of wet, formerly frozen, dirt). There was a little unmapped trail in this area that I followed for fun which passed a vernal pool and a very stoic female mallard.

I walked briefly along East Border Road and then went back into the woods for some more wandering, slowly making my way towards E4-4, which had a pond that was still slightly frozen! I also passed a group of about 13 preteen boys with 13 shih tzus? It was mystifying and terrifying, I got OUT of there fast!

I hiked the network of roads around Gate 35 and eventually made my way to the Fells Reservoir, passing at least 70 robins on the way and some animal that seems to have exploded (fur EVERYWHERE). I always thought the Fells Reservoir was like the ones on the Winchester/Medford side - closed to the public, but it was very clearly open to hiking as long as you stayed on the trails, and it was STUNNING. 

I hiked along the reservoir for a little and then circled around the restricted area which had something burred underground, I'm guessing pumps and water storage and the works. I'm really looking forward to coming back! I made my way to F5-1, hit a few hanging chads around there, and then followed the Cross-Fells Trail all the way back to the car!

Step-by-Step

- Park at Flynn Rink.

- Start hike by crossing Woodland Road and entering Gate 33 onto Woodland Path.

- At E4-7, turn right.

- At E5-1, turn left onto Rock Circuit Trail.

- At E5-2, turn left onto Hemlock Pool Path.

- At E4-13, turn around.

- At E5-3, turn right.

- At Highland Ave, turn around.

- At E5-3, turn left onto Hemlock Pool Path.

- At Gate 54, turn left onto East Border Road.

- At jct., turn left onto path.

- Hike triangle around E4-14, then continue on Hemlock Pool Road toward Gate 35.

- At Gate 35, turn around.

- At E4-3, turn left.

- At E4-1, turn left onto Reservation Path.

- At Woodland Road, turn around.

- At E4-2, turn right.

- At E4-4, turn around.

- At E4-2, turn right onto Reservation Path.

- At F4-5, turn right to circle Fells Reservoir.

- Hike the circle around the restricted area, and then hike towards F5-1.

- From F5-1, turn right onto Hemlock Pool Road.

- At nearest point to Rock Circuit Trail, turn around.

- At F5-1, turn sharply left onto Cross-Fells Trail.

- Follow Cross-Fells Trail back to car.

Middlesex Fells Reservation Map

Photo Album

Southern Lawrence Woods Tracing Loop (Middlesex Fells Reservation)

Southern Lawrence Woods Tracing Loop (Middlesex Fells Reservation)

Hike Type: Tracing Loop

Distance: 5.67 miles

Elevation: 427 feet

Time: 2 hours, 13 minutes
Hiking Challenges: 52 Hike Challenge 2026

The Hike 

It's officially Fool's Spring! Super warm (60s) temperatures in early March. I drove over to the Fells after school and was hoping to finish up the Lawrence Woods section of the reservation, with the liklihood of dreadful rotting snow keeping me grounded. It felt absolutely crazy and wonderful to be hiking in a t-shirt and shorts. I left the snowshoes in the car but brought the spikes - I wouldn't need either of them, but man, I wish I brought the gaiters! 

In the first two minutes of my hike I think I hit every possible trail condition (I was wrong, there were going to be more and worse conditions later on) with rotting monorail, dry ground, and mud. The air felt amazing, though! I'd get warm and cold pockets of air, which was very fun. The stream was flowing wonderfully toward Lincoln Road as I crossed a couple of bridges and observed many spur trails that led to private property. There was also a significant amount of dog poop - I'm guessing partially due to the access to private property but also some has likely been in the snow for months now. Every now and then I'd hit patches of dirt and it was WONDERFUL. 

I had to really pay attention at points because of how many unmapped trails there were. The trail to South Border Road from C6-5 was entirely unbroken, which made for some slow, squishy trail breaking in bare boots (this was the only spot where snowshoes could have been helpful). 

I continued to connect dots, working my way towards the Gate 3/Medford High School corner, and noticed that someone was MAD about the dog poop. So mad that they wrote notes on little orange flags and stabbed them into the piles of poop with a poop bag attached... Wild! Even funnier is that this added to the litter on the ground. The flags read: "I AM A DOG OWNER. THIS IS EMBARASSING. PLEASE PICK UP AFTER YOUR DOG." I saw at least 10 of them throughout my hike, with the highest concentration being around Gate 3.

The trail was exceptionally sneakily wet between B6-16 and B6-10. Both of my shoes plunged through what seemed to be a semi-stable monorail, through ice, though slush, and into inches of water. My feet were SOAKED. There was some more of this trail condition in the B6-15/B7-1/B7-2 corner of my hike. In fairness, I expected this condition for the whole hike, and I was only getting it for a fraction of my time, so I guess I'll be grateful? 

That same corner of my hike was interesting. Three trail branches led to the Medford High School parking lot that did not seem over-welcoming, while two others led to athletic fields that were basically flooded and got wildly close to peoples' back yards. Either way, I was happy to have them done! I also found an Iron Rung at B7-2, which was fun to see.

With some more cerative maneuvering, I accidentally ended up on an unmapped trail and basically started to bushwahck to finish up my map for the day. I passed a human-less dog (the human was like 0.25 miles away, which was crazy to me), a mountain biker (why??), and more angry poop flags. I followed another series of unmapped trails to get back to the easternmost woods road (passed a little knot-swing, which was fun to see!), and eventually made my way back to the car. 

This hike absolutely wiped me out, but I was feeling super satisified that I finished this corner of the park. Speaking from a few days in the future, I am also happy to report that I have ZERO hanging chads in this area, so I'm officially done with it!

Step-by-Step

- Park across from Gate 7 on South Border Road.

- Start hike at Gate 7.

- At C6-7, turn right and hike road.

- At C6-6, turn around.

- At C6-7, turn right.

- Hike Triangle at C7-2/1, then hike to Gate 4.

- At Gate 4, turn around and veer left.

- At C7-1, continue straight/left.

- At C6-5, turn right onto trail.

- At South Border Road, turn around.

- At C6-5, turn right.

- At B6-14, turn right.

- At B6-8, turn around.

- At B6-13, turn right.

- At B6-12, turn around.

- At B6-13, turn right.

- At B7-6, turn left onto trail.

- At Keith Road, turn around.

- At B7-6, turn left onto road.

- At B7-5, turn right onto trail.

- At terminus, turn right.

- At B6-10, turn around.

- At B6-16, turn right.

- At B6-15, turn left.

- At B7-1, turn right and follow loop.

- At B6-15 again, turn right.

- At B7-1, turn left. 

- At B7-2, turn right and hike trails.

- Return to B7-2, turn right.

- At B7-3, turn left.

- At B6-16, turn around.

- At B7-3, turn left.

- At B6-17, turn right onto trail.

- At B7-5, turn right.

- At B7-4, turn left.

- At Gate 3, turn around.

- At B7-4, turn left.

- At B7-3, turn right.

- At B6-11, turn around.

- At B6-12, turn left.

- At B6-13, turn right.

- Soon after, turn left onto unmarked trail.

- Follow unmarked trail to easternmost road, then turn left to return to car.

Middlesex Fells Reservation Map

Photo Album

Skyline, Reservoir, Molly's Spring Loop via Long Pond Parking (Middlesex Fells Reservation)

Skyline, Reservoir, Molly's Spring Loop via Long Pond Parking (Middlesex Fells Reservation)

Hike Type: -Oo- Loop

Distance: 2.24 miles

Elevation: 220 feet

Time: 45 minutes
Hiking Challenges: 52 Hike Challenge 2026

The Hike 

It's concert day! Whenever I have a day where I need to be at school at night, I try to get at least a little bit of time in in the Fells to get out of the building and get outside. It was 26 degrees out with a nice little snowpack (I probably should have brought spikes with me) and I didn't have much of a plan at all! I started on Molly's Spring Road and turned onto the Skyline Trail, mostly because I needed to pee! The Skyline Trail was less packed down, but still fine for bare boots. I accidentally got off of the Skyline Trail at one point and landed on the possible closed to public use West Dam Road, but it was pretty! I jumped onto the Reservoir Trail/Mountain Bike Loop for a bit and continued to hike out, and then I found out a plumber came to my apartment and made an absolute mess AND the pianist for my chours got sick... The stress had arrived! I turned around and made my return trip on the Reservoir Trail to Molly's Spring so I could get back to school and start solving problems. Thankfully, I heard an owl hoo-ing to cheer me on, which did lift my spirits!

Step-by-Step

- Park at Long Pond Parking Area.

- Start hike on Molly's Spring Road.

- At B4-4, turn right onto Skyline Trail.

- At B4-13, accidentally turn left and follow mapped, and then unmapped path to West Dam Road.

- At West Dam Road, turn right.

- Realize you are on West Dam Road, and then merge right onto Reservoir Trail.

- At Gate 12, turn around.

- At B5-4, continue on Mountain Bike Trail.

- At next jct., continue straight onto Reservoir Trail.

- At B4-6, turn left onto Molly's Spring Road.

- Return to car.

Middlesex Fells Reservation Map

Photo Album

Wright's Tower Loop (4x) (Middlesex Fells Reservation)

Wright's Tower Loop (4x) (Middlesex Fells Reservation)

Hike Type: Lollipop Loop-Loop-Loop-Loop

Distance: 2.34 miles

Elevation: 479 feet

Time: 49 minutes
Hiking Challenges: 52 Hike Challenge 2026

The Hike 

It took 9 days, but time for the first hike of 2026! I had my work holiday party at 4pm and got out of work at 2:45pm, so I drove over to the fells to lap Wright's Tower, which was actually a perfect way to kill an hour! It was a warm 46 degrees out, all I had were jeans and my waterproof boots, and I was off! I first did the loop clockwise, but did counter-clockwise for the second, third, and fourth loops so I could ascend the yellow trail. Trails were WET. Like bad mud season wet - a combination from snowmelt and rain. There was just a little bit of ice at the junction of Quarry Road and Wright's Tower Road, but not a problem at all. The yellow Wright's Tower Trail was pretty dreadful with the slippery mud, but I made it work! Before I knew it, four laps were done, and it was time to get over to the Great American Beer Hall (only five minutes away!).

Step-by-Step

- Park at Bellevue Pond parking area.

- Start hike at Gate 5/Quarry Road.

- Before D6-1, turn right onto Wright's Tower Road.

- At Wright's Tower, continue on Wright's Tower Trail (yellow).

- At D6-5/Wright's Tower Road, turn around.

- At Wright's Tower, descend along Wright's Tower Road.

- At terminus, turn left onto Quarry Road.

- Repeat loop two more times.

- After hitting the tower four times, follow Quarry Road back to car.

Middlesex Fells Reservation Map

Photo Album

Mid-Northern Lawrence Woods Tracing (Middlesex Fells Reservation)

Mid-Northern Lawrence Woods Tracing (Middlesex Fells Reservation)

Hike Type: Tracing Loop

Distance: 3.65 miles

Elevation: 322 feet

Time: 1 hour, 7 minutes
Hiking Challenges: Middlesex Fells Reservation Tracing, 52 Hike Challenge 2025

The Hike 

Another day in the Fells! I'm chipping away at the Lawrence Woods section of the reservation, mostly becuase it's the closest section to school and it's the dark times. I was feeling proud of myself for getting out for a second day in a row! It was a WARM 47 degrees with sunny skies and almost no breeze. Trails were a bit muddy at times, but mostly fine. I started my hike by getting a small loop on the main side of the reservation before crossing South Border Road and digging back into the middle portion of the northern Lawrence Woods!

It felt so good to be outside (per usual), so good that I wasn't even annoyed at the wildly unfriendly hikers this park seems to attract. I followed the Cross-Fells Trail up Ram's Head Hill, which was 80% crushed needle ice (pretty satisfying to walk on). This stretch of trail had some old communication wires overhead for a portion - I guess to that pole or old foundation? 

I meandered my way over to the Mustang Trail/Whitmore Brook Road area and heard some commotion through the woods, it almost sounded like sports, which was confusing considering it was December 18th. I made it onto Whitmore Brook Road and followed it to the busy MA-38. The trail proper was nice! Kind of like a Burma Road in the Blue Hills, but less wild. I backtracked for a bit, following more old communication lines, and then continued up toward B5-5, which passed a narrow strip of wetlands.

Now I made my way over to the Mustang Trail, which brought me to Medford High School (the commotion WAS sports!). I walked along the back parking lot before dipping back into the woods (unsigned) and then hit another stretch of the Mustang Tram before making my return trip back on Ram's Head Road. I even passed a super chunky bunny!

My drive home reminded me (unfortunately) of why I'm medium-adverse to the Fells - it was LONG. Well over an hour. It hurt. Still glad I got out, though!

Step-by-Step

- Park at Cross-Fells Trail on South Border Road.

- Start hike on Cross-Fells Trail toward B5-15 and C5-13.

- At C5-13, turn right.

- At C5-14, turn right.

- At terminus, turn right.

- Cross South Border Road.

- Follow Cross-Fells Trail to Ram's Head Hill.

- At B5-13, turn right.

- At B5-12, turn right.

- At B5-11, turn left.

- At B6-2, turn right onto Cross-Fells trail..

- At B6-1, turn right, continuing on Cross-Fells Trail.

- At terminus, turn left onto Whitmore Brook Road/Cross-Fells Trail.

- At terminus, turn around.

- At previous junction, continue straight on Whitmore Brook Road.

- At B5-5, turn right.

- At B5-11, continue right.

- At B6-2, turn right onto Cross-Fells Trail.

- At B6-1, continue straight onto Mustang Loop Trail.

- At Medford High, follow parking lot left and reenter woods.

- Follow path back to B6-1.

- At B6-1, turn right onto Cross-Fells Trail.

- At B6-2, turn right to continue on Cross-Fells Trail.

- At B6-3, turn right onto Mustang Loop Trail.

- At B6-10, continue straight, leaving Mustang Loop Trail.

- At B6-11, turn left onto Ram's Head Road.

- Follow Ram's Head Road back to car.

Middlesex Fells Reservation Map

Photo Album

Northern Lawrence Woods Tracing (Middlesex Fells Reservation)

Northern Lawrence Woods Tracing (Middlesex Fells Reservation)

Hike Type: Tracing Loop

Distance: 3.21 miles

Elevation: 282 feet

Time: 1 hour, 3 minutes
Hiking Challenges: Middlesex Fells Reservation Tracing, 52 Hike Challenge 2025

The Hike 

Time for some more redlining/tracing in the Fells! I had to mentally hype myself up, but I'm glad I did! The mental block of short afternoons and driving home afterwards is always tough. I got to the trailhead with just under an hour until sunset, so I got moving right away! I parked at the trailhead opposite Gate 9, hiked a few spurs on the main side before crossing South Border Road (carefully) to hit the Lawrence Woods area for the first time. I had no plan besides explore!

The trails were a little wet from snowmelt and the treetops were golden with the setting sun. There were occasional sunset views through the trees, which was nice. I hiked mostly along the old roads, making sure to hit the spurs of triangles littered about. I wiggled my way up to Ram's Head Hill, which had a tall pole of sorts up top and the foundations of an old structure at the true summit (naturally I looked for a survey disc, no luck!).

I continued my wiggle over to the "90mm Site," and was first greeted by a large concrete disc with rebar sticking out of the top, almost as if they used the rebar to unscrew the circle from the ground? The trail turned to moss-covered pavement as it passed old foundations and concrete structures - it was a really interesting area! I eventually found an informational kiosk that detailed what exactly I was walking around...

From Missles to Monarchs: Restoring a Pollinator Meadow

Where you are now standing was selected as an anti-aircraft defense site for the United States during the Cold War to house a 90mm battery, though the Nike missiles themselves were never installed. After this site was closed, the state park continued to mow the field, preserving an area "rich in butterflies, with 67 species recorded between the late 1960s and early 1980s." Mowing soon after ceased and invasive plants took over. The butterflies disappeared.

In the spirit of environmental sustainability, Medford Girl Scout Tripp 75198 took on the challenge of reestablishing the pollinator meadow in 2018.

Pollinators (animals, mainly insects that pollinate plants) are crucial to the health of the entire environment; its grasses and flowers, our fruits and vegetables. With cooperation from DCR and the Friends of the Fells, the Girl Scouts planned, researched, planted, and weeded to restore the pollinator meadow over the course of a year.

There were MANY unmapped trails between Ram's Head Hill and the 90mm Site, so I had to check AllTrails a few times to make sure I was on a mapped trail still. My return trip involved Whitemore Brook Road, a few spurs off of that, and then a little wiggling around B6-5/4/9/3/6, before returning back to the car and carefully crossing South Border Road again!

Step-by-Step

- Park at Gate 9.

- Start hike on access road.

- At "No Trespassing" sign, turn around.

- At B5-8, turn left onto Skyline/Reservoir/Bike.

- At next jct., turn right onto path.

- At Gate 9, turn left onto South Border Road.

- At Gate 8, carefully cross the street and hike in on Ram's Head Road.

- Hike network of triangles at B6-7/B6-8, then follow path towards Ram's Head Hill.

- At B6-6, turn right.

- At B6-5, continue straight.

- At B5-12, continue right.

- At B5-13, turn right onto Cross-Fells Path.

- At B6-5, turn right back onto road.

- At B5-12, turn left onto road.

- Just after, turn right onto trail.

- Hike network of trails at 90mm Site, then turn left onto Whitmore Brook Road.

- At Gate 11, turn around.

- Hike spur to Southfield Road, continue on Whitmore Brook Road.

- At B5-5, turn sharply right onto spur to Clearwater Road, then retrace steps.

- Continue straight through B5-5 toward B5-11.

- Hike triangle at B5-11, turn continue left.

- Before B6-5, turn right onto Cross-Fells Path.

- At B6-4, turn left.

- At B6-9, turn right.

- At B6-3, turn right.

- At B6-4, continue right/straight.

- At B6-6, turn right.

- At B6-7, turn left.

- At B5-14, turn right onto Cross-Fells Path.

- Carefully cross South Border Road, follow road to car.

Middlesex Fells Reservation Map

Photo Album

Wright's Tower, Red Cross Path, Cross-Fells Path, Middle Road (Middlesex Fells Reservation)

Wright's Tower, Red Cross Path, Cross-Fells Path, Middle Road (Middlesex Fells Reservation)

Hike Type: Tracing Loop

Distance: 3.81 miles

Elevation: 417 feet

Time: 1 hour, 12 minutes
Hiking Challenges: Middlesex Fells Reservation Tracing, 52 Hike Challenge 2025

The Hike 

Okay, with my first few ski days behind me and squeeking in another 4000 footer, it's time to get back on-track with hiking. I always struggle this time of year with motivation since the only place I can realistically hike for more than an hour is the Fells which doesn't always excite me, only hiking for an hour isn't exciting, and getting minimal elevation also isn't exciting. That being said, everytime I go I think "I should do this more!" Thankfully, motivation came in the form of returning tubas to the high school and seeing their production of Cindarella, so I had some time to kill (plus, as per tradition, I'm comically behind on my 52 Hike Challenge hikes for Nov/Dec.

It was a windy afternoon and a chilly 30 degrees. My only goal was to see the view from the tower and then meander on trails that I had not yet meandered - off I go! The yellow trail up to the tower was made up of frozen mud (and two unleashed dogs) and I immediately found myself wishing I had a buff, gloves, and a fleece (instead of the hoodie I wore to school). The view was wonderful, as always, though. I passed some needle ice on the descent via Skyline Trail, and followed the Skyline Trail over to the Red Cross Path, avoiding some confusing criss-crossing unmapped trails and frozen swamps.

I hit a triangle along the Red Cross Path and maneuvered around some more unmapped paths around C5-25 before turning onto the more-rugged Cross-Fells Path. I followed the Cross-Fells for a while, and then eventually made a sharp turn onto the Reservoir Path, which had nice tree views to the Reservoir, which was not yet frozen. I still am wondering about the practicing legality of hiking the paths around the reservoir...

I hiked the network of loopty loop mini-trails around C5-4, which were mostly grown-in, and then made my way over to East Dam Road and the Bike Loop, which had a nice long series of NEMBA bridges. I was starting to work up an appetite! 

Now on Middle Road, the sky was illuminated with wonderful pastels as the sun barely poked through the sun. I made my down some unnamed paths, eventually returning to Bellevue Pond! It was a really nice afternoon in the woods, and now that it was dark at 4:20pm, I made my way over to Sweetgreen in Burlington and then schlepped up to the high school for some theater!

Step-by-Step

- Park at Bellevue Pond.

- Start hike on Quarry Road.

- After D6-5, turn right onto Wright's Tower Path.

- At D6-4, turn left onto Skyline Trail.

- At C6-3, turn right onto Red Cross Path.

- Hike triangle at C6-4, continue on Red Cross Path.

- At C5-25, turn left.

- At C5-17, turn right onto Cross-Fells Path.

- At C5-11, turn left to continue on Cross-Fells Path.

- Hit spur at C5-10, continue on Cross-Fells Path.

- At C5-5, turn right.

- At C5-6, turn left to continue on Cross-Fells Path.

- At C4-9, turn left onto path.

- At C4-8, turn left onto Reservoir Trail.

- Hike network of spurs around C5-4, then continue left on East Dam Road.

- At C5-8, turn sharply right onto Bike Loop.

- At C5-7, turn left onto Middle Road.

- Hike Triangle around C5-14/C5-15, continue on Middle Road.

- At C5-14, continue straight/veering slightly right onto continuation of road grade.

- At terminus, turn left onto road.

- At C6-2, merge and continue onto Middle Road.

- At unmarked junction, turn left and return to car.

Middlesex Fells Reservation Map

Photo Album

Bellevue Pond, Wright's Tower, and Others Loop (Middlesex Fells Reservation)

Bellevue Pond, Wright's Tower, and Others Loop (Middlesex Fells Reservation)

Hike Type: Tracing Loop

Distance: 4.04 miles

Elevation: 427 feet

Time: 1 hour, 23 minutes (1 hour, 18 minutes moving)
Hiking Challenges: Middlesex Fells Reservation Tracing, 52 Hike Challenge 2025

The Hike 

A tell-tale sign that it's officially the "dark times" (i.e., after daylight savings time) is that I'm hiking in the Middlesex Fells again! My only goal was to see the view from Wright's Tower and meander on trails that I think I haven't hit before. It was 49 degrees, windy, and mostly cloudy, but overall pretty pleasant. I started my hike from Bellevue Pond, per usual, and hit St. Denis Road and the spur path off of it to get started. It was nice and quiet in the woods.

I was here in between school getting out and parent-teacher conferences - I didn't realize how badly I needed this time in the woods! I had really lost the after-school hiking this year (which happens every year, in fairness) due to dating, marching band, and overall exhaustion. Bellevue Pond was essentially a marsh, which I'm guessing is due to overall low water levels plus summer? I passed a bunch of massive squirrels and one well-behaved off-leash dog as I climbed to Wright's Tower, which per usual had just a wonderful view. 

I ended up doing my best to connect unblazed paths that I thought I still needed - only tough part was that there were MANY criss-crossing unmapped paths I had to navigate around, too. I did my best to stay on-track with moderate success!

Once back at Bellevue Pond, I went back up to the tower and enjoyed a beautiful sunset. The clouds parted just enough for the sun to shine through, and it made my body feel very happy. I really needed this!

Step-by-Step

- Park at Bellevue Pond.

- Start hike on Quarry Road.

- At D6-5 turn right onto St. Denis Road.

- At terminus, turn around.

- At unsigned jct., turn left onto spur.

- At South Border Road, turn around.

- At St. Denis Road, turn left.

- At D6-5, turn right onto Quarry Road.

- Near Wright's Tower Road, hike short trails there and then climb to Wright's Tower.

- At Wright's Tower, follow Skyline Trail toward D6-1.

- At D6-1, turn right onto Quarry Road.

- At D5-7, turn left onto trail.

- At D5-6, turn right onto Skyline Trail.

- Before C5-21, turn left onto trail.

- At terminus, turn left onto Red Cross Path.

- At C5-25, turn right onto trail.

- At C5-17, turn left onto Cross-Fells Path.

- At C5-16, turn left onto Skyline Trail.

- At C5-24, turn right onto trail.

- At C5-23, continue on trail.

- At C5-22, turn left onto road.

- At C6-1, turn right onto trail.

- At South Border Road, follow trail on left, accidentally following a northern unmapped trail.

- At Middle Road, continue onto trail to Bellevue Pond.

- At Bellevue Pond, turn left.

- At C6-9, continue around Bellevue Pond.

- At D6-3, turn right onto Quarry Road.

- Before D6-5, turn left to climb to Wright's Tower.

- Enjoy the sunset.

- Descend via Skyline Trail to D6-2.

- At D6-2, turn left onto Quarry Road.

- At D6-3, turn right onto road.

- At C6-9, turn left onto road to car.

Middlesex Fells Reservation Map

Photo Album

Rock Circuit Trail Loop (Mostly) (Middlesex Fells Reservation)

Rock Circuit Trail Loop (Mostly) (Middlesex Fells Reservation)

Hike Type: Lollipop Loop

Distance: 4.68 miles

Elevation: 558 feet

Time: 2 hours, 4 minutes
Hiking Challenges: Middlesex Fells Reservation, 52 Hike Challenge 2025

The Hike

As it is apparently now a springtime tradition, I had a school musical to see in the evening, so I went for a hike to kill some time! The show was Six! Teen Edition at the high school I teach marching band. The hike in question was the Rock Circuit Trail at the Middlesex Fells, one of my favorites! It was a chillier 60 degrees out with a breeze and plentiful sunshine. I suited up, carefully crossed Woodland Road, and I was off!

The hike began on the Cross-Fells Trail/Woodland Path, which featured a wonderufl early spring green tunnel. The trail circled a pond on the left and then I turned onto the Rock Circuit Trail just after, which passed another pond on the right, and later a larger one near E4-4. 

I had done this and variations on this loop numerous times, and I really didn't remember this stretch, which made it exciting! I passed a young shagbark hickory (thank you, Seek app) that had some really unique spring leafing/budding, and then the Rock Circuit Trail turned onto a road grade at the Fells Reservoir fence.

I realized I accidentally cut a corner when I turned onto the Melrose Path, which offically turned this into a tracing hike. Some men ran past me in sandals, and I worked my way up to the first open rock slab, which was delightfully warm with many singing birds all around.

Continuing on, I passed a baby garter snake in the leaves and worked my way to the crossing of the Fellsway. I scrambled up the next rocky knob after crossing the road and met some really neat harlequin flowers. 

I noticed a large fire ring on the left of trail just before it climbed up White Road, which had a brand new sign! I LOVE the sign, and I noticed Melrose Rock had one just in the distance, too! I also notice that someone's been kissing the white blazes with pink lipstick, which was a choice... I enjoyed the views from White and Melrose Rocks and continued my way over to the top of the Cascade, which was more of a dribble at this point, but still lovely from up high.

It was so nice to have leaves on the trees again. I caught up to a weridly silent duo as I climbed up the next nameless rock, followed by a few more nameless rocks with more harlequin flowers. There was a sign on view-less Black Rock, with many tent catepillars as well. From here until the next Fellsway crossing, the blazing became challenging to follow, and didn't always match up with the map. 

I wiggled my way over to Pinnacle Rock, which had a fantastic view and many survey holes. I kind of free-wandered off of Pinnacle, eventually following more white blazes (official-looking ones!) that weren't on the map. These blazes brought me to the communication towers and unmapped Ziggy's Rock, which had an excellent view of Boston and Great Blue Hill.

Eventually, the blazes brought me to Pinnacle Path, and then back onto the mapped stretch of the Rock Circuit Trail, which paralleled the Fellsway before crossing. The blazing and footbed were much easier to follow, now, too, and a kind driver stopped on the Fellsway to let me cross!

The Rock Circuit Trail continued through some wetlands before climbing again, passing some DCR "be kind" signs that I'd never seen before. The sun felt heavenly on a nameless rock, and I got a great view to Boston again from Boojum Rock. The new sign for Boojum was placed in a spot that had Boston directly behind the sign, which was a great touch.

From Boojum, I continued onto the MIT Observatory and then followed the Rock Circuit Trail almost all the way back to the Cross-Fells Trail, but I took a path I hadn't hiked before to cut a corner and get back to the car. I easily crossed Woodland Road, and made my way to Panera for some dinner before the show (the show was fantastic!).

Step-by-Step

- Park at Flynn Rink.

- Cross Woodland Road.

- Begin hike on Cross-Fells Trail/Woodland Path.

- At E4-8, turn left onto white-blazed Rock Circuit Loop.

- At F4-6, accidentally turn right onto Melrose Path.

- At F4-2, turn right back onto Rock Circuit Trail.

- After Pinnacle Rock, continue to follow white blazes to unmapped Ziggy's Rock, Pinnacle Path, and rejoin mapped section at F5-11.

- At F5-11, turn left onto Rock Circuit Trail.

- At E4-18, turn continue right onto path.

- At E4-7, turn left onto Cross-Fells Trail/Woodland Path.

- Cross Woodland Road, return to car.

Map of Middlesex Fells Reservation

Photo Album