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Great Blue Hill via Skyline Trail

MODERATE 736 reviews
#1 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

walking

running

forest

lake

views

wild flowers

wildlife

rocky

hiking
muddy
scramble
10 days 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
10 days ago

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

hiking
muddy
15 days ago

hiking
muddy
rocky
scramble
17 days ago

recorded Recording - Nov 11, 12:55 PM

hiking
29 days 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!

hiking
rocky
30 days ago

Busy but not crowded. Great trail!

hiking
rocky
30 days ago

Good workout, very rocky. Trails busy. Will do it again!

Great trail close to the city! Blazes were occasionally hard to follow.

hiking
rocky
1 month ago

hiking
rocky
1 month ago

hiking
scramble
1 month ago

Great way to get a wood bath and a gorgeous view of Boston and the harbor. Lots of cute dogs too.

hiking
rocky
1 month ago

Nice trail for a weekend potter. Family friendly however some steep rocky sections. We saw a snake eating a frog.

hiking
rocky
scramble
1 month ago

hiking
1 month ago

Took us about 2 hours to finish it. It has Some pretty views. Best time to go it is during the autumn

hiking
rocky
scramble
1 month ago

lots of people and more challenging than expected. a lot of up and down. gorgeous trails and some pretty views.

hiking
rocky
2 months ago

Wonderful moderate hike, the boy I babysit (8) and I had a wonderful time on this trail! It took us about 2 hours to complete the whole loop.

hiking
rocky
2 months ago

hiking
rocky
scramble
2 months ago

hiking
2 months ago

Beautiful! Make sure to go up the stairs in Eliot Tower

hiking
bugs
rocky
scramble
2 months ago

fun for the family! lots of elevation change, met many different hikers along the way. warning, there were a LOT is bees around Elliot tower

hiking
rocky
2 months ago

hiking
rocky
2 months ago

On a moderate to hard scale definently closer to hard, recommend a walking or trekking pole. But worth it, beautiful scenery best on a clear day, amazing Boston skyline.

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