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Great Blue Hill via Skyline Trail

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Blue Hills Reservation

Great Blue Hill via Skyline Trail is a 3 mile heavily trafficked loop trail located near Milton, Massachusetts that features beautiful wild flowers and is rated as moderate. The trail is primarily used for hiking, walking, 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.

Length 3.0 mi Elevation gain 820 ft Route type Loop
Dogs on leash Kid friendly Hiking Nature trips Walking Running Forest Views Wild flowers Wildlife Rocky
Description
Waypoints (1)

This relatively short hike in the forests of the Blue Hills Reservation has some great views of the Boston skyline. Eliot Tower is a fantastic lookout point to see the entire Boston region. Although the trail is not too technical, trekking poles can help you keep your footing in tricky areas.

Weather
UV Index
Daylight
Reviews (1720)
Photos (1792)
Recordings (1921)
Completed (3079)
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Jason Marchant
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Hiking
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Nancy Jaquins
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Hiking

Many hills and rocky, a great workout!

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Gil Shoham
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Hiking

Really nice! I went for a round to see the top of the ski slopes at the top. Soooo worth it!! Great view. Can get kind of windy and cold at the top but the actual hike was fine

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Gabriel Szentpaly
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Hiking

Beautiful picturesque fall hike

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Dimitry Tsukerman
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qian sun
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Jennifer Jageler
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Hiking

Nice trail. Lots of elevation change. Very crowded on weekend afternoon.

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Mia Byun
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Jonathan Richardson
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Lisbeth Pena
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Hiking

Amazing and we were beginners. Great workout!!

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jacqueline rodriguez
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HikingRocky

Pretty cool for beginners

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Ami Sayag
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Emily Elmen
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HikingRockyScramble

I’m new to hiking and have been doing trails rated “moderate” all over MA for the last few months. I would say this is on the harder end of the “moderate” spectrum. A fair amount of scrambling up rocks where you really need to watch your footing or you could lose your balance down a pretty steep drop, so keep your eye on your footings. Otherwise this hike is great! Not a dull moment!!! And the views are worth the scrambles :)

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Steph Moreau
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Hiking

Great trail! Lots of stone stairs for ascension/decent but also smaller loose rocks (watch those ankles). I was able to complete the loop (clockwise) in just over two hours to catch a beautiful sunset at the last summit (Great Blue Hill).

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J D
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Hiking
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Devon Cooper
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Hiking

Lots of bouldering up and down the mountain but super fun! definitely didn't feel like we hiked 4.2 miles

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Hannah Pham
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Hiking

Awesome trail and well marked. Lots of ups and downs kept thing interesting!

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Don Chan
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Michael Blanchette
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Michael Fingerman
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Hiking

Much more rocky than reviews show. Don’t be fooled by the mileage, it’s technical at times!

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Nikki Lonardo
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Hiking

The views at the start were a 10/10 and the foliage was nice, super clear day. The trail is misleading due to the constant up and down changes. A little hard to follow with all the random intersecting trails too. Definitely had to keep the map up the whole time to navigate !

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Yoly Santos
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Hiking

This is not a hike for people expecting a workout. Short and not challenging, but beautiful views.

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Eric Gorodetsky
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Hiking

Brutal rock climbing

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Jenny Dare
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Hiking

Awesome!

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Lisa Sugarman
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Hiking

Great moderate loop. Well marked and fairly crowded but great views and beautiful foliage. Just wish dog owners would haul out their poop bags. Too many abandoned bags littering the trail. Otherwise a stellar hike.

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Michaela Olson
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Hiking

Ducked out slightly early, knees were getting tired, but a fun hike!

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Rich L
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Hiking

Fun. Lots of climbing. Lots of people on a beautiful day

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Joe Red
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Brian Quill
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