Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: o-o Loop

Distance: 4.52 miles

Elevation: 1,201 feet

Time: 1 hour, 43 minutes
Hiking Challenges: 52 Hike Challenge 2025; Great Blue Hill Summits

The Hike 

I really wanted to drive up to the Whites to hike Mt. Wolf, but a late night compounded with another day of high anxiety, I opted to sleep in a bit and revisit the Blue Hills, which I was not mad about! I was only mad that I was still feeling anxious, but alas... I made it to the Trailside Museum parking area around 8:00am, which was a little busier than yesterday, but by no means full. The weather was yet again wonderful at 67 degrees with relatively dry air and a nice intermittent breeze. My body was feeling tired after yesterday's hike so I was planning to take things slower.

That plan did not last - once I got moving I truly sailed up the Eliot Path - my legs were feeling good! I made it up to the summit and looped around toward Eliot Tower, where I noticed a stone on the ground that read "BMB Take this with you. Do not leave it behind!" - I am incredibly curious what that could be about!

Descending along the Skyline Trail, I got stuck behind a bunch of guys in golf attire, but eventually got to pass them and made my way into Wildcat Notch, which smelled wonderfully floral. My watch had been misbehaving again, showing low heart rates when it should have read 160+, but it fixed itself once I was climbing up Hemenway Hill.

There was a slight traffic jam at the headwall at the Breakneck Ledge junction, but I scrambled up the side no problem. At the top of the scramble, I ran into a woman with three dogs who I saw yesterday - she recognized me! I got stuck behind another duo that wouldn't let me pass on Hancock, but soon I got past them and made it down. At the bottom, I took a swig of water and saw a family of three deer staring at me! They moved before I could get a good photo, but when I was getting water at the water fountain, there was a hummingbird at the headquarter's hummingbird feeder! That made up for the deer.

I was much sweatier than yesterday at this point, and I drank too much water before my Houghton climb, because I was feeling ROUGH. I also saw god, again. My heart rate got up to 187, which is high for me. I did survive, though, and then I got to zone out for the next bit of time. There were some bugs near the stream crossing between Houghton and Great Blue Hills, but nothing too bad.

Up next was the final push up Shadow Cliff back to the summit of Great Blue Hill. I think I did almost pass away, but I stopped right after the scramble to question my life choices and catch my breath. I opted to not take a victory lap today as I was nearing death, and instead to just enjoy my second summit and a nice walk down Sonya. I passed a guy peeing into the bushes on my descent, and when I got to my car, realized I, yet again, did not lock it. Oh well!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Hike around observatory building clockwise.

- Follow gravel path to Skyline Trail.

- At terminus, turn left onto Skyline Trail.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At Eliot Circle, turn left.

- At gravel path (same as before), turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to parking lot.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya + Victory Lap) (Blue Hills Reservation)

Skyline Loop via Trailside Museum (w/ Sonya + Victory Lap) (Blue Hills Reservation)

Hike Type: Lollipop Loop-Loop

Distance: 5.79 miles

Elevation: 1,539 feet

Time: 2 hours, 10 minutes
Hiking Challenges: 52 Hike Challenge 2025; Great Blue Hill Summits

The Hike 

I am officially back in New England! I am sad to say goodbye to my Jersey Summer, but it is nice to be back and beginning to put my life back together. My body woke me up at 6:45am on my first morning back, so I decided to go to the Blue Hills. It was BEAUTIFUL out. 56 degrees (!!), blue skies, and not many people. I was going to breaking in a new pair of Merrel Moab 3s (the hiking shoes) and a new pair of Darn Tough socks. I put band-aids on my nipples after the pain from the past two hikes, I put my weighted water bottles back in my pack (just two out of the three), and off I went!

The new shoes were delightfully grippy on the usually slippery rocks along Eliot Path, and soon enough I was back on my favorite local hill! It was nice to be hiking on a trail-trail again, instead of the Tourne's gravel path. There was some new construction around the observatory which in turned closed the spur path to the Eliot Circle/Skyline Trail, so I had to follow the gravel path past the buildings to catch Eliot Circle further down, which I was not upset about.

The construction looks like they're redoing the sandy area at the base of the tallest communication tower and possibly doing some erosion control along the Eliot Circle. Closer to the tower, the Eliot Circle has been widened to a dirt road, I'm guessing for construction vehicles (and maybe to match the path on the other side of the circle). 

The view from the tower was delightful and I only shared it with a few others before descending along the Skyline Trail North. There were a suprising amount of rattling red squirrels in the trees as I crossed paths with a surprising amount of people. I also tightened my shoes, as they had gotten loose (the beauty of breaking in new ones!). 

This hike is definitely harder than the Tourne, but I am also grateful to have had the Tourne while in Jersey. I made it up and over Wolcott, Hemenway, and Hancock Hills and down to HQ, where I topped off my water bottle. I played some Pokemon while walking along Hillside Street and then shoved my way past a bunch of people standing and chatting on the Skyline South Entrance(??). I got Humbled By Houghton yet again (I came close to death, I fear), and began to cross paths with many folks I had already seen.

Somewhere in the sag between Big Blue and Houghton I realized that I, yet again, left my keys in my car! Why do I do this! Thankfully it was still just beautiful out. I also was lamenting that the nice weather was not here to stay - next week is Band Camp and highs are mid-90s all week. It will NOT be nice.

I eventually made it to the final climb up Great Blue Hill, and I think I truly saw god I came so close to death. I summited again and descended along Patriots and Sonya - both of which seem to have been patrially mowed in the past month. There were a suprising amount of people out on the ski slopes, which was kind of nice to see. I did have one dog charge at me, which was annoying, but it recalled once it started sprinting.

At the bottom, I was feeling strong and brave and decided to take a victory lap! There were a lot of people on Eliot Path now, but I wanted to get a third summit in, so I was a big boy and turned around at the parking lot. I was much more tired this time, but still moving strong (doing this also helped cool the anxiety I've been dealing with recently). I made it to the top and then descended along the ski trails again, where I was surprised to see a dad had set up a tent with his two toddlers and his dog? He was taking them on a nature scavenger hunt, which was actually really cool. I think the kids might have been a little young for any of it to have any impact, but good effort!

Soon enough I was back at the car and doing a stressful grocery shop before continuing to unpack my life from 6ish weeks in New Jersey!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Hike around observatory building clockwise.

- Follow gravel path to Skyline Trail.

- At terminus, turn left onto Skyline Trail.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At Eliot Circle, turn left.

- At gravel path (same as before), turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to parking lot.

- Repeat Eliot Path - Eliot Circle - Patriots - Sonya loop for extra credit.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya; CCW)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.23 miles

Elevation: 1,181 feet

Time: 1 hours, 45 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

Same thing, different direction! I was feeling CRAZY and decided to hike my usual loop in the opposite direction! I had a sleepy drive and it was another hot, hazy, humid day at 85 degrees. To really make things exciting, I knocked my Nalgene off the top of my car and it EXPLODED. I swear, I am truly the only person capable of shattering Nalgenes. I decided I'd still go for the hike and bail if I got too hot/dehydrated, knowing that there is a water fountain at the halfway point.

I made it one minute into my hike before I was pouring sweat. I crossed paths with a trail runner who I had seen dozens of times before and soon enough I was up top at the summit. There was a guy working on the big antenna, which was fun to see. Descending Skyline South, I saw another one of those large spiders I saw yesterday! I could just make out the top of Buck Hill from a standing view before the steepest descent. It was kind of fun to be going in reverse - it felt like a whole new route!

The intermittent breeze truly saved my life throughout this hike. The water crossing near the cool rocks was basically dry and the other one was down to a trickle. Climbing up Houghton Hill, I noticed a really pretty red hue on many of the trees that isn't as noticeable from the other direction. There was an unfortunate amount of dog poo bags on Houghton, but also a pile of what I believe to be coyote poop, so that was exciting?

While descending Houghton, one of those big spiders LANDED on my arm, I smacked it, and it POPPED. Made a complete mess. It was horrible. I made my way down to Hillside Street and awkwardly walked past the line cars, ready to fully camel up at the water fountain. I also got to enjoy watching a groundhog investigate the stables!

I climbed up Hancock Hill, up and over Hemenway, and found myself missing the owl on Wolcott. The final climb up Big Blue was buggy and slow, but overall much easier than climbing up the other side. I think overall this was a much easier loop on the muscles, heart, and lungs, but the steeper descents killed my knees!

An EXCELLENT gust of wind hit me on Eliot Circle as I worked my way back to the top, again wishing they had a water fountain up top! My descent was wonderfully windy and I decided this would be my last Sonya until the fall when the grass begins to die - it has officially gotten too long for my liking (and for my phobia of ticks).

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.21 miles

Elevation: 1,171 feet

Time: 1 hours, 42 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

After a few days of getting caught up on sleep after my Californian bender, I was finally feeling back to normal. I made it to the Trailside Museum parking area after work in 82 degree, humid-but-breezy weather. The drive was slow, but I was excited to get some hiking in! I cruised up the Eliot Path, passing a couple sharing a joint on the way (I would see them later near the tower and one of them was NOT having fun). 

I continued from Great Blue Hill over to Hancock Hill on tired-feeling legs. I'm unsure if my legs have been feeling more tired becuase I have just been more tired, if the humidity is just taking its toll, or the third water bottle I added to my pack is just enough extra weight that I really feel it... Who knows!

I descended Hancock and climbed Houghton in one tank of gas, but it did NOT feel good! I also noticed an absurd amount of LARGE spiders on this hike (quarter-sized), and they were all the same type of spider but like a mile away from each other, hmmm. I noticed some dried out lady slippers as I hiked from Houghton to Great Blue Hill, where I also noticed the baby blueberries beginning to transition to blue! There was a wind after Shadow Cliff that I think saved my life since I was SOAKED. 

I noticed some daisies near the summit as I descended down to the ski area, which was surprisingly hazy. I played some pokemon as I descended and saw a red-tailed hawk fly away from a tree and let out its trademark "CAAAAAAWHHHHHHHH," which was pretty sweet.

Near the end of my descent, I noticed some foam-like substance on some of the grass at my feet. According to Seek, it was caused by a type of spittlebug. According to Wikipedia:

"The larvae are well known for the self-generated foam nests which can be observed during spring in meadows (especially on cuckoo flowers, Cardamine pratensis, and broom, Genista, species). The larvae in the foam nests are largely protected from predators and also get the necessary moisture for the appropriate development and temperature, so their mortaility remains low even in bad weather. The larval stage lasts about 50 days. The adults leave the foam nest only when it is completely dried. This takes about ten days. The females mate soon after.

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.24 miles

Elevation: 1,175 feet

Time: 1 hours, 45 minutes
Hiking Challenges: 52 Hike Challenge, Great Blue Hill Summits

The Hike 

As is unfortunately a theme this spring, I had yet another angry, sleepy drive after school and simply needed to blow off some steam in the woods. It was a warm 83 degrees out with wildfire smoke in the air. The sky was white and the sun was orange, which was hauntingly pretty. There were an annoying amount of cars in the parking lot and I was already sweating while putting my shoes on - oof!

The climb up Eliot Path was buggy but visually beautiful due to the faux golden hour. The shade felt significantly cooler than the sun, which was helpful. There were unique, hazy views from Eliot Tower and I trailed a group of four women loudly talking about toenail health in front of me before finally letting me pass near Wildcat Notch. My legs felt wobbly as I climbed up Wolcott Hill and I finally caved and put on bug spray, which unfortunately did help.

I didn't see the famous owl, but I did hear some bullfrogs in the first col, and I soon made it up and over Hemenway and Hancock, too. My hips were still chafing slightly from my trip to Hibbard, Square Ledge, and Passaconaway, and I did stop to relieve my bladder on Hancocok.

At the reservation headquarters, I made use of the water fountain, which provided me with some wonderful, chilly water - thank goodness! I watched bugs drown in my sweat as I was getting humbled by Houghton Hill, and as per usual I zoned out from Houghton to the final climb up Big Blue. My legs were TIRED going up Shadow Cliff, and I found myself wishing for a water fountain up top after this climb. I ran into a bunch of bikers at the summit, which was also annoying (a theme today), but I had a wonderful descent down Patriots & Sonya. I also got to watch the ski area management setting up their new ice cream stand! I was not in the best headspace for this hike, but I am glad to have done it nonetheless.

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Eliot Circle & Sonya)

Skyline Loop via Trailside Museum (w/ Eliot Circle & Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.83 miles

Elevation: 1,194 feet

Time: 2 hours, 24 minutes (2 hours, 13 minutes moving)
Hiking Challenges: Great Blue Hill Summits

The Hike 

AAAANNNNDNDDDD we're back! I had another brutal drive down, but any time in woods is better than no time in woods! It was 76 and a little hazy with a few clouds in the sky. Sarah and I planned to meet, but she was running 20ish minutes behind me and I had to PEE, so I decided I would get started before her, take care of my business, and then meet her at the top. I had to hike with no straps buckled on my pack my bladder was so full. I took care of business partyway up the Eliot Path and then continued to struggle my way up - I did my first "leg day" in about 6 weeks this morning, so my legs were FEELING it. 

I passed someone hiking down while smoking a cigarette, which was... interesting. Once on Eliot Circle, I took a "victory lap" around the loop to kill time before Sarah made it up. On the Eliot Circle, after the ski area spur trail, the black oaks were growing in quickly, making the trail a bit of a gentle car wash. Once I rounded the corner near the Skyline Trail I was gifted with a wonderous breeze. I then crossed paths with a guy in a full sweatsuit that was fully soaked, and then I climbed the tower and interruped a... happy couple?

I made my way around and to the summit, where I played some Pokemon Go while I waited for Sarah. Once she arrived, we were off! I told her I was going to be slow, and boy, was I correct!

We took turns ranting about our bosses from Big Blue to Hancock - made the time go super fast! We admired the pink lady slippers on the route, and then the harlequin flowers and blue toadflax on Hancock. We continued on Hillside Street and struggled up Houghton Hill (I think she was just pretending to be tired, she's so nice), and made our way back up Gerat Blue Hill. Mile 3 took 38 minutes, which might be a new slow record!

From the top, we descended along Patriots and Sonya to wrap up a slow, but rewarding hike.

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- Hike full Eliot Circle loop.

- At jct. with Eliot Path, continue on Eliot Circle.

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.23 miles

Elevation: 1,178 feet

Time: 1 hours, 36 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

Back to school after Memorial Day Weekend and I had a HORRIBLE drive down to the Blue Hills (took over an hour and 10 minutes, which is ridiculous). There were many cars at the trailhead, but I was determined to persevere! It was a hot, but not opressive 83 degrees out with some bugs flying about, but I got right to work!

I was moving slower than usual but still at a good pace up Eliot Path. It was hazy overhead with some clouds, and I was blessed with catching a shiny Zigzagoon on Pokemon Go once at Eliot Circle! I summited Great Blue Hill and began my descent, where I passed a vibrant, massive Blue Jay. I wiggled through an unnaturally large amount of people in Wildcat Notch and climbed up Wolcott, which had a pretty juxtaposition of burned understory and new growth at the summit.

In the col, I sadly did not see the owl from a couple weeks ago, but I did see some harlequin flowers up on Hancock Hill! The blueberry bushes are starting to bloom, too. I descended to the sounds of many tweets and chirps and noticed a chunk of rock broke off at the bottom slab of the Hancock descent - I wonder if weather or human casued?

Hillside Street was wonderfully breezy but dreadfully stinky - a weird combination of swamp, horse, and cars. The flowers of the lesser periwinkle at the base of Skyline South were all gone, and the lower stretch of this climb was surprisingly muddy. I had added another water bottle to my pack just for some extra weight and my legs definitely were feeling it on the Houghton Climb, but I was greeted with another wonderful breeze once at the top.

I zoned out for a while until I was back on the summit of Great Blue Hill, where I descended the much narrower ski area spur path. The Summit-to-Circle stretch was pretty grown in but the Circle-to-Ski was still in good condition. I passed a brown bird with a red head and a pointed beak at the Patriots headwall (might have been a male Yellow-shafted Northern Flicker, but I'm not 100%). 

I was blessed with one more wonderful breeze once on Sonya, which had taller grass than last time, but was still manageable without getting any ticks. Overall, a nice afternoon! Now off to Costco for my weekly chicken!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.16 miles

Elevation: 1,165 feet

Time: 1 hours, 23 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

I didn't plan on hiking on this Friday, but my school day ended POORLY and I desperately needed to blow off some steam, so back to the Blue Hills I went! It was a hot 81 degrees out, humid, and I left my water at home - solid start! I opted to do yet another lap of the Skyline Trail loop in hopes of taking the local legend status from Sarah (sadly, I did not succeed). I did blast up Eliot Path up to the summit and enjoyed a breeze as I flew down Skyline North to Wildcat Notch, where were were bullfrogs cheering me on! I passed a familiar trail runner and familiar bugs climbing up Wolcott, which smelled smokier than usual - probably because of recent rain?

Speaking of familiar, the owl was there again - third day this week! I wonder if it's next is nearby or something. I conitnued onto Hemenway and Hancock, crossing paths with more people than I cared for. There were lots of catepillars crawling around Hancock Hill and I made use of the water fountain at the park headquarters for the first time, hoping I wouldn't fully perish from dehydration.

I was cooled off by a wonderful breeze on Hillside Street and the Skyline Trail South smelled like a unique combination of burned trees and fresh flowers. I nearly passed away climbing up Houghton Hill, getting my heart rate up to 189 (which is RARE for me). The only thing that brought me back to life was seeing my first pink lady slipper of the season near Five Corners Path! I audibly gasped in excitement, I was so happy!

I continued my rage hike back up to the summit, dreamed of drinking water, and began to descend via the ski trails. It was hot on Patriots and Sonya, but there was an amazing breeze back at the parking lot, which felt like a reward. I was DRENCHED in sweat - I made sure to hydrate once home, but even still I cramped up on the couch. Tragic! I did get three PRs on Strava, so that's another win!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.18 miles

Elevation: 1,175 feet

Time: 1 hours, 33 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

Happy Wednesday! I had a brutal drive down to the Blue Hills after my department meeting (3 seperate accidents!). The original plan was to Skyline Loop again with Sarah, but she got there a half hour ahead of me so I gave her my blessing to go on without me. She counter-challenged me to try to catch up to her, and I do love a challenge... To my dismay, the parking lot had at least 20 cars in it (thankfully the trail was fine). Temps were in the mid-70s and I was hiking by 4:11!

Starting up Eliot Path, I was still in awe with how green everything has recently become. There was a wonderful breeze accompanying me while I gunned it up the hill. I didn't think I would catch up, but I did want to give it a try! I hiked through a sea of gnats at the road crossing as I continued to blast off - this was a zone 4/5 hike. 

Near the summit, Sarah texted me that the owl was still there in the Wolcott col! She was about 15 minutes ahead of me at that point. Just after summiting, I realized I left my car unlocked and left my keys IN my car... ugh. I thought about aborting mission, but the thought of seeing the owl again and catching up to Sarah weighed too heavily to give up - onward!

I flew down Great Blue Hill and found the owl in the Wolcott col, now on a different limb right up on a tree trunk. I got nervous when he wasn't in the exact same spot, but it does make sense that he moved at some point in the past 24 hours. I got passed by a trail runner who I always see who runs while on the phone (and with the phone on speaker phone...) and fought muscle fatigue as I shot up Hemenway and Hancock. Legs were JIGGLY. 

There were lots of chirping bugs in Hancock Hill and the Skyline South entrance at Houghton smelled like flowers. I was yet again humbled by Houghton (I got my 2nd fastest time on Strava), but then a miracle happened! I caught up to Sarah on the Houghton descent! I gave a loud ca-caw and then we chatted up and over Great Blue Hill and down Sonya yet again. What a fun way to end the hike!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.28 miles

Elevation: 1,181 feet

Time: 2 hours, 6 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

Back with Sarah for a Skyline Loop! We met after a SLEEPY drive after work and got right to it! Eliot Path was straightforward and we passed a few groups of hikers, and a garter snake! We had a wonderful breeze from the top of Great Blue Hill and continued onto the Skyline Trail North. When we made it to the col between the two high points of Wolcott Hill, we crossed paths with two girls who couldn't have been older than 18. We crossed paths, but they quickly turned around and said "do you guys want to see an owl?" Sarah and I obviously said "YES." They led us probably 50 feet down the trail and there it was - a big barred owl just chilling in a tree! It was so cool, and we thanked the girls profusely for showing it to us. They said "yeah we saw your camera and figured you'd like it!" It looked around and scratched its head. We were OBSESSED.

After watching the owl for five-ish minutes, we continued on and over Hemenway and Hancock. The climb up Houghton was humbling as always, and soon enough we were climbing up Great Blue Hill again for round two. We opted to descend on Sonya while the grass was still low. The view to Boston from Patriots was growing in with all the leaves, and we found a tick further down (on the grass, thank goodness). Soon enough we were back at our cars and on the way home!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Great Blue to Hancock Hills; Border & Wolcott Paths (Blue Hills Reservation)

Great Blue to Hancock Hills; Border & Wolcott Paths (Blue Hills Reservation)

Hike Type: Loop

Distance: 4.17 miles

Elevation: 794 feet

Time: 1 hour, 53 minutes
Hiking Challenges: Great Blue Hill Summits; Trail Trace the Blue Hills

The Hike 

It's Tuesday and I was hiking with Sarah again! We met after school and did our usual zoom up Eliot Path. It was 78 degrees out, which felt HOT hot. The sun was shining strong and there was a nice breeze. There was also the classic yellow hue of springtime pollen in the air which was... fine. Sarah was feeling a bit gassed, so we decided we'd make our way over to Hancock Hill via the Skyline Trail and then assess if we wanted to continue on Skyline or pivot to something else!

Great Blue to Hancok was nice. Sarah and I yapped about skiing and weddings, and we were soon greeted with a wonderful breeze to dry off our sweat-soaked shirts on Hancock Hill. We decided to skip the second half of Skyline and head down Hancock Trail, which has my favorite views in the reservation. Someone had recently gone in and spray-painted new yellow blazes to mark the correct footpath, which was appreciated. There were some tent catepillars around and just wonderful views to Boston, the ocean, the islands, and other Blue Hills. We descended down, making our way to Base Path Connector (I told her if we're ditching the Skyline Trail we gotta get a few trail segments I needed for my map), where Sarah tragically stepped in dog poop! She washed it off in a brook with a stick, and then we continued on.

The return trip was along Border and Wolcott Paths, keeping it nice and easy. Only hinderance was the bugs! They were officially back out with a vengeance - mostly zooming into our ears, noses, and eyes. Brutal. We picked up the pace and soon made it back to the car! We ended the hike as any good friends would, with a limp-wrist handshake, since we were both wet with sweat, but a firm handshake was too formal.

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

- At Hancock Hill, continue left onto Hancock Trail.

- At terminus, turn left onto Hancock Hill Path.

- At terminus, turn left onto Base Path.

- At 1183, turn left onto Base Path Connector.

- At 1165, turn left onto Border Path.

- At 1100, turn right onto Wolcott Path.

- Follow Wolcott Path to north parking area. 

- Follow sidewalk on left back to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Skyline Loop via Trailside Museum (w/ Sonya) (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 3.97 miles

Elevation: 1,145 feet

Time: 1 hour, 28 minutes
Hiking Challenges: Great Blue Hill Summits

The Hike 

After a wonderful April break, it was back to the real world. I headed down to the Trailside Museum south parking area after school for a classic Skyline Loop. The trailhead was busy, and a dog ran out of its car at me, but at least it was a warm 76 degree, sunny day! I got started right away, accidentally forgetting my camera in the car. I blasted up Eliot Path, was drenched in sweat once at Eliot Circle, and made it to the summit of Great Blue Hill in no time! The fencing had been removed around the flagpole, allowing access to the highest point outside of the observatory again!

I took a big swig of my warm Nalgene and continued along, passing a couple hiking up Wolcott Hill with a Trader Joe's pag, implying they were hoping for a picnic? They wandered into the burnt woods before noticing me continuing on the trail, which I think got them back on. 

I passed and crossed paths with many more people and a couple of off-leash dogs (side-eye...) and enjoyed how the trail was noticeably more green than the last time I wandered here. From the viewpoints on Hemenway and Hancock, I especially enjoyed seeing the springtime greens (even if they're the color of vomit) coming in all around. The tent catepillars were also hard at work on Hancock.

Down at Hillside Street, I was horrified to find out that the porta potty had been moved from the stables to the Bugbee Path trailhead across the street! This is completely fine in case of an emergency, but not worth the extra effort for a little urination, in my opinion. The lesser periwinkles at the base of Skyline South were absolutely thriving and my legs were screaming (as per usual) heading up Houghton Hill. I passed a women who hocked the most incredible lougie and made my way back up to Great Blue Hill. 

I made the executive (and correct) decision to follow the ski trails down. It was so wonderfully clear out - Wachusett, Watatic, Monadnock, and the Pack Monadnocks were all clearly in view. I was following a few people and their (off-leash) dog on Sonya, but it was still a wonderful walk. Once at the car, I threw the towel down on my driver's side seat and ZOOMED to Costco for my rotisserie chicken!

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- From summit, descend to ski area.

- Follow Patriots and Sonya down.

- Near bottom turn on Sonya, turn right back onto Eliot Path.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album

Great Blue Hill, Circle Trail, Bartol & Carberry Paths (Blue Hills Reservation)

Great Blue Hill, Circle Trail, Bartol & Carberry Paths (Blue Hills Reservation)

Hike Type: Loop w/ Spurs

Distance: 5.27 miles

Elevation: 750 feet

Time: 1 hour, 50 minutes
Hiking Challenges: 52 Hike Challenge 2025; Trail Trace the Blue Hills, Great Blue Hill Summits

The Hike 

Another warm, grey day in the Blue Hills during another long, stressful week. The plan was roughly to get some cardio in while waiting for an important phone call from a friend - super fun (sarcastic)! I parked at the north Trailside Museum parking area and followed a herd path to the trail that wraps around the Trailside Museum before making my way to and climbing up the Eliot Path, which was wet and slippery from the rain and humidity. I realized a few minutes into my hike that I, yet again, forgot to start my Garmin and AllTrails... ugh. There was a little snow left on Patriots and I swam my way through the humidity to the summit, which thankfully had a heavenly breeze. 

I continued down Skyline North and some spring peepers cheered me on as I climbed up Wolcott. I got the call I was waiting for as I climbed up Hancock (naturally, when I was out of breath), and then I kind of zoned out for a while, slowly meandering down Circle Trail and Chestnut Run Path. The call ended very well and I continued onto Bartol Path, where I lost service. I love the Bartol Path on a cloudy day - it has a really unique, seculded energy to it. There were yellow daffodils just off the trail at the terminus, and then I continued around Rotch Path, passing my first humans of the day (two off-leash dogs and two humans, one of which was barefoot...), and made my way to Carberry Path, which was still delightfully mowed.

I was feeling much better after that phone call, and I played some Pokemon Go as I made my way out of the woods on Wolcott Path. Happy spring!

Step-by-Step

- Park at north Trailside Museum parking.

- Start hike on Wolcott Path.

- Soon after starting, follow herd path on right.

- Join path and hike south around Trailside Museum fence.

- After jct. with Abigail Adams Trail kiosk, turn left onto Eliot Path.

- At 1055, turn right onto Eliot Circle.

- At road, turn left onto Summit Road.

- At jct., turn right onto spur.

- Summit Great Blue Hill.

- From summit, follow path east.

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

- At 1063, turn right onto Skyline Trail North.

- At jct. after 1170, turn right onto Circle Trail.

- At 1180, turn right onto Breakneck Ledge path.

- At 1203, turn right onto Chestnut Run Path.

- At 1175, turn left onto Border Path.

- At 1135, turn right onto Bartol Path.

- At terminus, turn around.

- At 1135, continue straight onto Five Corners Path.

- At 1140, turn right onto unnamed path.

- At 1121, turn right onto Rotch Path.

- At 1114, turn left onto Border Path.

- At 1100, turn right onto Carberry Path.

- At terminus, turn around.

- At 1100, turn right onto Wolcott Path.

- Follow Wolcott Path to car.

Blue Hills Reservation Map

Photo Album

Skyline Loop via Trailside Museum (Blue Hills Reservation)

Skyline Loop via Trailside Museum (Blue Hills Reservation)

Hike Type: Lollipop Loop

Distance: 4.31 miles

Elevation: 1184 feet

Time: 1 hour, 34 minutes
Hiking Challenges: Great Blue Hill Summits; Trail Trace the Blue Hills

The Hike 

Time for a warm, cloudy Skyline Loop! Plus, a last hike of March, which turned out to be my most-hiked month ever with 17 days in the woods! (My previous record was 16 made this past June, followed by a few other months in the past where I hit 16 hikes, but some days had multiple hikes). Big Blue was in a cloud when I was driving on I-93, and I was delighted to see only a few cars at the trailhead when I landed. It smelled wet, like springtime, and I realized that I forgot my Nalgene and only had some old, stale water left in a smart water bottle... oops. It was 57 degrees, the skies were gloomy, and I was off!

There was one duo ahead of my on the Eliot Path, but they went up the easier way, leaving the whole way up to myself. The rocks were wet which required some careful/slippery footing, but nothing too bad. It was foggy and spooky up top, which was kind of fun, and the top of the communications antenna was barely visible. I also noticed an absurd amount of orange peels around the Eliot Tower?

Continuing on the loop, I admired the deer tracks at the base of the Wolcott climb and caught up with the duo from earlier, passing them as I entered Downtown Crossing. The antenna was still in a cloud when I made it to the viewpoint from Hemenway, and when on Hancock I hit the clockwise portion of the Circle Trail before continuing down the slippy rocks. 

I made use of the porta potty (I'm glad I've reprogrammed my bladder to not need to go that bad until I get to a porta potty, versus having to dodge into the woods and hope no one is around). At the base of Houghton I saw some of the first purple flowers of the year (lesser periwinkles, I believe). I swore my way up Houghton and suffered from wobbly legs on the way back down to the col. My internal playlist at this point was a wild mashup of "I Want Candy" by Aaron Carter and "RÓA" by VÆB for the 2025 Eurovision Song Contest (it slaps, highly recommend). 

I heard some peepers in the swamp near the headwall, cursed my way up again, and hit my second summit! The clouds lifted slightly, and I was delighted at how people-free this hike was. Naturally, I wrote that note and passed a woman I had seen before on a previous hike, did the usual "hey hows it going," and she gave me a "GOD LOVES YOU" pamphlet... I felt a bit bamboozled and trapped, and I also had to hold onto it because I wasn't about to leave a trace! Cruel. 

 

Step-by-Step

- Start hike from Trailside Museum parking on Eliot Path (red dots).

- At terminus, turn right onto Eliot Circle. 

- At next jct., turn left onto Summit Road.

- At next jct., turn right onto spur trail to Summit.

- Descend summit towards Skyline Trail South.

- Turn left onto Skyline Trail, and then right onto Skyline Trail North.

- Follow Skyline Trail North to Circle Trail jct. after Hancock Hill Summit.

- Turn left onto Circle Trail.

- At jct., turn left onto Skyline Trail, follow to Hillside St.

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

- After stables, turn right onto Skyline Trail South.

- Follow Skyline Trail South to Eliot Circle.

- At jct., turn right to summit Great Blue Hill.

- Retrace steps to car.

Blue Hills Reservation Map

Photo Album