Explore the most popular 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.


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Milton, Massachusetts Map
trail running
14 days ago

Parked along Chickatawbut Road near gate. Went up Buck Hill first then over to Hawk Hill but ran out of time. It was getting dark so couldn't quite make Chickatawbut Hill too. Was hoping these 3 peaks would net out at +1,000' elevation gain. This will have to wait for another day! Great trek, give it a try. Only tricky thing is crossing the road but friendly drivers will stop for you, just be careful. Cheers!

17 days ago

Got lost a few times (twice) because some markers aren’t as easy to spot but the trail is pretty good. Definitely recommend

I️ grew up right on this hill. I️ bring my dog all the time up there, and she runs freely. Just be careful because there are some horses on the trail some times.

There are two ways to go. You can take the shorter way which is a smaller loop of the hill. Or, you could continue straight down and do parallel to the road and do the bigger loop. Nice views, and I️ love being in the woods.

This one is a more challenging hike (but I am a beginner) at points it gets very steep but the views at the end make it worth it

This is a great hike, Buck hill has several great views, including a nice one of Boston. Recommend ascending Tucker hill first and ending your hike with the red trail back; takes 1-2 hours.

Easy trail! love the company!!

Grew up hiking these trails with my family!!!

The trail was kinda tough to follow, we ended up taking the wrong trail at the weather observatory. Make sure you bring a map with you!

This is one of my favorite trail in the Blue Hills. I especially like Eliot Tower the most. A great place to have a picnic in the picnic area.

3 months ago

Great view of the Boston skyline from Eliot Tower. Thought it was going to be a rock scramble at 0.7 miles in, ended up being a nice rock staircase instead.

park at Washington street and green street. difficult going up, nice pavilion at top with great view of boston. enjoyed it!

very crowded on a Sunday morning! started off to the right-trail was good but harder than expected. lots of up and downs before getting to the top of great blue hill. advise going early on weekends. parking lot was completely full when leaving around 1pm.

Great to do with your kids. Very flat with the exception of the final .2 miles up the hill. However , it is well maintained with a
Rock staircase ascending most the .2 miles.

4 months ago

This trail definitely earned the hard rating, but if you’re up to the challenge it’s a lot of fun! The views from the observation tower are fantastic!

Lots of fun to climb, really a steep start, but the views are worth it. Parking was kind of far away

Love this place, especially when I've got the Blues!
Trek on my friends!

I added Houghton Hill and Wolcott Hill as I was trying to max out my elevation gain. I got over 700' gain between these peaks and without doing Great Blue Hill. Sweet!

Very enjoyable hike. If you are going with kids go clockwise. this makes the steeper inclines uphill.

5 months 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.

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.

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