Skyline Loop from Trailside Museum (Blue Hills Reservation)
Hike Type: Lollipop Loop
Distance: 4.55 miles
Elevation: 1155 feet
Time: 1 hour, 58 minutes
Hiking Challenges: Blue Hills Winter Trace, Blue Hill Grid, Great Blue Summits, Sunset Six
The Hike
Happy Valentine’s Day! It was (another) beautiful, spring-like day with temperatures in the 50s, and after my recent skiing weekend, I wanted to get in a “fitness hike.” My go-to fitness hike is always the Skyline Trail Loop (N & S) either from Park HQ, or from the Trailside Museum by adding in the red-dot trail(s). I decided to go big for this hike, and made my way to the north Trailside Museum parking lot (I like the south one better, but it gets crowded during ski season). I retraced my steps from my sunset hike last week around the back side of the Trailside Museum and eventually linking up with the Eliot Path to climb all the way up to the Eliot Tower. I’ve said it before, but I love this trail. It’s reminiscent of the rocky, slabby trails in the whites, and gets the heart pumping without taking any lives. There were beautiful pre-golden hour colors shining on the trees, and I decided to not climb the tower this day because there were a few people already up there.
I also love this loop because you don’t need a map or a phone to follow - just stay on the Skyline Trail! I made my way steeply down the North branch of the Skyline Trail, first down Great Blue Hill, through Wildcat Notch, and then up Wolcott Hill. There was a new bridge over the usually muddy section in the notch which was a welcomed surprise. The climb up Wolcott always takes me by surprise - my legs were already tired!
The trail through Wolcott is featureless yet beautiful. It’s been really interesting watching the forest regrow after the fires of last spring - I find it amazing how quickly it can repair itself. There is still obvious sign of damage, but it’s far less obvious than it was last time I was up this way.
Meandering over a bonus knob of Wolcott Hill, the Skyline Trail then dips out at what I call “times square” - a large intersection with a trail map at 1141, before climbing up Hemenway Hill with a few scrambles. There’s a great view of Great Blue Hill just after the high point of Hemenway Hill. Continuing on, the trail slightly descends and then climbs steeply twice to the high point of Hancock Hill, which is full of views. The best view of Great Blue Hill, in my opinion, is soon after the last steep climb, and then there’s amazing views of Chickatawbut, Buck, and the surrounding hills further down.
Descending Hancock Hill is always a little dicey - equal parts steep, slabby, and either wet and/or dusty (the views help!). Once at Park Headquarters, I followed the herd path sidewalk along Hillside Street, passing the DCR stables, before reaching the next junction, where the Skyline Trail South steeply climbs up Houghton Hill. This section of trail is in my book for “always knocks my on my ass for no good reason” - but I made it up in one piece! I started flirting with making it to the top for sunset, but I knew that I didn’t want to sprint up the trail like I essentially did last week. I would check the time and assess at 1083.
Leaving Houghton Hill, the trail meanders up and down, never too aggressively. It crosses a small stream just after 1143, some wetlands after the junction with Five Corners Path, and then finally the beginnings of the Blue Hill River. When I finally made it to 1083, the sunset was about 10 minutes away, and I was feeling the burn at this point. I allowed myself to let go of the sunset, and slowly worked my way up. After reading some of the old guidebooks, either the junction at 1083, or just at the big scramble is called “Shadow Cliff/Shadow Point” - still trying to figure out which one! Either way, I made it up in one piece, and continued my slog up the final stretch, delighted to see the intersection marker at 1066!
I turned left to continue on Skyline Trail, then turned right to hit the summit of Great Blue Hill. Just as I turned the corner around the observatory, I was surprised with the tail end of the sunset! I was so happy and it felt so good to be illuminated by that famous orange glow. I touched the plaque at the summit and enjoyed the sun’s final moments for the day - what a fantastic way to end my day!
With that final boost of endorphins, I followed the trail down to the Ski Area from the summit, crossing the Eliot Circle, to get a few final photos of the ski area before finishing my hike. I took the Eliot Circle back to 1055, and then quickly made my way down the Eliot Path to the south Trailside Museum parking lot (light was getting low so this was easier), and then I followed the sidewalk in front of the museum back to my car. A great day!
Step-By-Step
Start hike at north Trailside Museum parking lot.
Hike trails around trailside museum to meet up with red-dot Eliot Path.
Follow Eliot Path to Eliot Tower.
From Eliot Tower, take Skyline Trail North all the way to Hillside Street.
Turn right onto Hillside Street.
Turn right onto Skyline Trail South.
Follow Skyline Trail South to 1066.
At 1066, turn left to continue on Skyline Trail.
At next junction, turn right onto trail to summit of Great Blue Hill.
Gawk at the surprise sunset, then take trail from summit down to top of the ski area.
Retrace steps from top of ski area to Eliot Circle, follow Eliot Circle clockwise.
At 1055, follow Eliot Path down to Trailside Museum south parking lot.
Walk in front of Trailside Museum to get back to the car.
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