Great Blue Hill via Skyline Trail

MODERATE 397 reviews
#2 of 49 trails in

Great Blue Hill via Skyline Trail is a 2.7 mile heavily trafficked loop trail located near Milton, Massachusetts that features a lake and is rated as moderate. The trail is primarily used for hiking, walking, trail running, and nature trips and is best used from April until October. Dogs are also able to use this trail but must be kept on leash.

Distance: 2.7 miles Elevation Gain: 702 feet Route Type: Loop

dogs on leash

kid friendly

hiking

nature trips

trail running

walking

forest

lake

views

wild flowers

wildlife

rocky

hiking
1 day ago

This trail is rated moderate but while we were on it we thought it was a little above that. Lots of up and down hiking, really good workout, but going down was a little treacherous- step carefully! I definitely slid down a little bit and got some good bruises. Still enjoyed the loop and had fun.

backpacking
off trail
rocky
26 days ago

1 month ago

Rocky and green. Really a good one for spring.

hiking
muddy
rocky
scramble
1 month ago

hiking
muddy
rocky
1 month ago

hiking
rocky
scramble
1 month ago

hiking
rocky
1 month ago

Amazing trail conditions. Even with a quick monsoon that passed through late yesterday and the frequency of rain the trails were drier than expected. Started off on the Skyline trail with the blue blazes. This trail wasted no time putting up some vertical numbers. Within 15 minutes your reward is some beautiful panoramic views. There’s several paths that cross the trail throughout the hike. Some marked well others not so much. I kept my AllTrails handy to stay on track. If I wasn’t pressed for time I would’ve done it all over again.

hiking
2 months ago

The trail was great for people just getting started to take on more difficult trails. There are some more challenging steep and rocky parts, but nothing too crazy. The trail was well marked and had a decent amount of foot traffic on the morning as it's part of one of the more popular trails.

hiking
bugs
muddy
2 months ago

hiking
bugs
rocky
scramble
2 months ago

Went up great blue hill and down coon hollow path. Definitely challenging on the way up, very rocky and narrow but it was fun! Coon hollow path down was super easy, barely any rocks and a nice wide trail.

hiking
muddy
2 months ago

A bit wet and mushy today but the rock tops were dry so that was good. Was trying to get +1000' elevation gain by redlining Great Blue Hill. Happy to report I DID IT!

hiking
muddy
rocky
scramble
3 months ago

hiking
muddy
rocky
3 months ago

hiking
3 months ago

Great trail! I believe some of the reviews below are for the full skyline trail, which is indeed more difficult. This shorter alternative is challenging enough that you feel like you’re getting a good workout but not so bad that you feel like you’re going to die from the challenge. Great views throughout. Very rocky so I definitely recommend hiking boots but I don’t feel like you would need hiking poles. Overall, took us about 3 hours to complete but that was with a few breaks to take in the views!

hiking
muddy
rocky
snow
4 months ago

hiking
6 months ago

amazing scenic view when you make it to the top

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