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Great Blue Hill via Skyline Trail

MODERATE 779 reviews
#1 of 50 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

walking

running

forest

lake

views

wild flowers

wildlife

rocky

hiking
1 day ago

Loved this path! It was really steep at parts, so make sure you have good knees and plan on getting out of breath, but it’s a satisfying workout! I accidentally took the wrong path near the weather station and ended up going down to a road even though it was still blazed with the same color, so keep checking your location to ensure you’re on the loop portion of this trail!

hiking
icy
muddy
snow
3 days ago

hiking
muddy
rocky
13 days ago

Nice trail, saw some woodpeckers pecking away. Great view from Eliot tower.

hiking
muddy
rocky
15 days ago

hiking
15 days ago

I would recommend this trail to those who are looking to go on a decent hike with rocks. It is dog friendly and there is a lot of great views by the tower. make sure to keep a close eye out for your blazes or else you might miss your turn. if this is your first time hiking I would not recommend this trail.

hiking
muddy
rocky
20 days ago

Nice hike, but a bit too rocky and steep for my 6 and 9 year olds. We completed but it was challenging for them.

hiking
icy
rocky
25 days ago

hiking
icy
muddy
29 days ago

Awesome trail!!!!! Great quick hike

hiking
icy
muddy
snow
1 month ago

Great hike on Christmas! Saw many others at the top. 65% ice.

hiking
icy
rocky
1 month ago

More ice than I expected on 12/25/19. Still very doable, just go very slow in the inclines.

hiking
flooded
1 month ago

hiking
muddy
scramble
1 month ago

Awesome hike. Quite challenging climbs and descents on the rocks at times but well worth it. One of the most challenging hikes in the region (non-mountainous area around metro Boston). I’d rate it “New England hard.” Make sure to turn after the bridge by the observatory so you go to South Skyline rather than going past the weather station then down the other blue trail section.

hiking
rocky
1 month ago

Beautiful view of Boston area at top of Elliott tower! Trail was challenging at times with slippery rocks.

hiking
muddy
2 months ago

hiking
muddy
rocky
scramble
2 months ago

recorded Recording - Nov 11, 12:55 PM

hiking
2 months ago

Completed as a solo hike, nice balance of rocky scrambles, flat paths and uphill/downhill. Saw some people along the trail on a Monday holiday, but not too busy. A nice loop!

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