Explore the most popular hiking trails near Milton with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

on Great Blue Hill Trail

hiking
2 days ago

This was my husband and my second hike this month and this trail was a fun challenge. We followed the path initially, but shortly after Eliot Tower, we mistakenly continued to follow the blue markers. The blue markers, after a certain point, does not follow the Great Blue Trail path. Instead, it takes you towards Canton and to a path that crosses the street.

This is a heavy traffic trail though and we saw many hikers with their dogs, dogs ranging from a lab to a corgi.

The views at the top of the hills and at the Eliot Tower are stunning!!!

There are a lot of hiking up and down large boulders/rocks. At times it was challenging, but doable for beginners hikers. The down did take a toll on our knees and ankles, but we are beginners.

I would love to do this path again in the winter.

TLDR: Go to this trail. Beautiful, green, remote, and appropriately related as moderate with some inclines/declines, passing from rocky trail to dirt.

Went on Sunday, 5/27 from about 2-4:38PM or so. We started on the side of the police station, up to Hancock Hill. Short 5 minute hike up and you get a beautiful viewpoint (see photos). A few minutes later to Hancock Hill where All Trails has the route split further to the west. We did this, but knew rain was scheduled for 4PM, so we stopped this side route with a couple hundred feet or so to go. Again, great views. As we continued we went down some other side trails exploring the lush forest, then back to the Great Blue Hill Trail.

Beautiful, thick forest throughout. Some fun crossings across logs. There’s a lot of downhill, so it seems like heading up on the Houghton Hill side would be much more difficult. Granted, there were some uphills for us. Wasn’t too crowded. Maybe saw 15 people total. No traffic noise, but heard or noticed one commercial jet.

AllTrails says 3.1 miles, though it’s close to 4.5-5.0. I didn’t monitor exact distance and writing this the day after, but apple health was about that when we finished. Of course we explored a bit off the GBH trail, but not enough to bump it by 1.5 more miles.

Moderate rating is appropriate due to the terrain and inclines. You will be walking over larger rocks, tree roots, etc. It’s not a smooth, flat, fire road like the Santa Monica Mountains. Was visiting family and wasn’t anticipating hiking, so didn’t bring proper boots or clothing. I’ve hiked for years in California in a pair of worn out Adidas so I had no problem in them on this hike. But, if I had my Salomon’s it would’ve been more comfortable and I would’ve taken more “risks” on some of the slicker, steeper inclined rocks. For inexperienced hikers, you will get tired and you should wear more appropriate shoes than sneakers.

Go hike, have fun, bring a bottle of water, and take your trash with you.

There are so many trails, it's hard to keep up which one you are doing. Anyway, just good if you can't get out of the city, nice little wood

Fine if you can't get out of the city, nice little wood. But it is crowed

First trail I hiked in the blue hills, good view from the observation tower!

Good quick hike, couple hours. The weather tower was the highlight.

hiking
1 month ago

I took my dog and it was a great hike! Perfect weather. A lot of people and there were a good amount of friendly dogs! One of my favorites in Mass!

Really nice loop early in the day. Half is pretty flat and woodsy, the other half has hills and rocks. The flat part was also nice because there was lighter traffic.

Good workout in a relatively short amount of time. Trail is well maintained and there are some nice views at the top. Tends to be very crowded.

beautiful views. Rocky.
difficult in winter.

Not too hard.

hiking
3 months ago

Nice hike, kinda crowded.

Some wide easy trails. Some steep & rocky. Very muddy in spots, but, hey, it was February.

hiking
3 months ago

The view was worth the hike

hiking
6 months ago

Hiked this trail in the wintertime following a snowfall and was not disappointed. Tough to believe you can find a serene landscape like this tucked inside the I-95 corridor! Great views and well-marked trails, with a few rocky/scrambling areas and several challenging inclines and descents. Good footwear is a must. Will hike the longer variation next!

hiking
6 months ago

Kids friendly. Wear good shoes

Magnificent trail

hiking
7 months ago

Always a good loop. short but nice.

Another perfect kid/dog friendly trail.

Nice short loop.

Start on Skyline Trail South to the Elliot Tower and finish Skyline Trail North. All the views will be near the end of the hike, about 3/4 of the way through, which is way more rewarding. If you go counterclockwise, you'll see all the views at the beginning then nothing but trails for the majority of the way. Fun hike!

on Great Blue Hill Trail

hiking
9 months ago

it was a beautiful veiw. it a must see.cant wait to see it in the fall

9 months ago

Great moderate climb. Well marked trail with beautiful views.

beautiful hike me and my famiky were so happy to be together. i love them so much. best day ever. i wish dad was still alive

hiking
10 months ago

Quick yet challenging hike. Great if you are in the mood to get outdoors and hike but are short on time. The hike starts off very moderate and then gradually gets harder, but nothing to difficult!

Best trail in the area in my opinion. Playful trek with a rolling accent to the tower. Lots of rocks to test stability and tree coverage for protection from wind and sun. Little creek crossing on the way down when there has been recent rain. Can be slippery and icy. 90 mins round trip if fit. Can take up to 3 hours for a novice. The inclines can be challenging for newbies so set expectations for those joining you.

hiking
11 months ago

Despite it being listed at hard, it is far from challenging for anyone hiking the blue hills. The terrain is mostly level, with a few crossovers onto the skyline trail and the red trail from trailside to great blue.

hiking
11 months ago

Beautiful hike. We did the Trail counterclockwise and found a lot of steep downhills scrambling down rocks. The next time we will do it clockwise. The 3.4 miles took a couple of hours.

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