Looking for a great trail near Boston, Massachusetts? AllTrails has 20 great hiking trails, trail running trails, walking trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails in Boston Harbor Islands State Park, we've got you covered. You'll also find some great local park options, like Boston Common or Boston Public Gardens. Just looking to take a quick stroll? We've got 18 easy trails in Boston ranging from 0.6 to 10 miles and from 0 to 177 feet above sea level. Start checking them out and you'll be out on the trail in no time!

walking

kid friendly

views

nature trips

bird watching

wild flowers

hiking

running

dogs on leash

road biking

wildlife

dog friendly

beach

city walk

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Definitely the coolest trail I’ve done that’s not a nature trail. The history comes alive during your walk and you’ll see many National Park sites! If you’re in Boston this is the #1 thing you must do!

One of the coolest parts of Boston. Be sure to visit the Holocaust remembrance, the USS Constitution, and the Union Oyster House! There’s a good smoothie place around there too, but I can’t remember the name of it. There was a lot of construction but it was all easy to maneuver.

hiking
no shade
1 month ago

Easy trail. No shade. But great views of the Boston Skyline

on Millenium Park

walking
1 month ago

Great place to walk your dog. Well trained, friendly dogs are off leash, less friendly dogs are kept on leash.

Although this is only listed as a 2 1/2 mile trail past 16 sites key in US history, this short and easy hike can take the best part of a full day in downtown Boston. Add the nearly 300 steps up the Bunker Hill monument and all side hikes and tours and expect 5 mile day. Awesome.

hiking
1 month ago

History, exercise and construction

hiking
1 month ago

I’m

Worth taking the tour. Very entertaining.

fun trail through the city of Boston. this is a mix of dedicated bike Lanes and crossings through major intersections. Better in the earlier part of a weekend due to traffic, both people and vehicle kind during a beautiful day.

I work in Boston and walking through or just a break after work is great! New Years Family fireworks are great! 7:00 pm

Amazing urban historical trail. I recommend the self guided audio tour that uses an app on your phone. You can get all the information at the visitors center.

hiking
1 month ago

Lots of bird and rabbits. Very well maintained.

hiking
1 month ago

Mostly paved but a few grass trails as well. Awesome skyline and Boston harbor views. Also views and smells of the wastewater treatment plant.

Great place to ride and watch the planes land at Logan .

Great way to get your steps in while learning about the Revolutionary War.

walking
2 months ago

Get a cannoli.

I would recommend this trail for someone looking for a dog-friendly trail or a trail with great picnic areas and views.

Great way to explore Boston on a self guided tour. I’ve lived here for 5 years and had never done the trail, so decided to on a beautiful Sunday afternoon. Amazing bits of history at each stop along the trail and some beautiful paths through some of Boston’s nicest areas. Highly recommend to both visitors and long time residents!

road biking
2 months ago

This paved trail connects Constitution Beach to Piers Park. The path is easy and is 2.4 miles in each way. Constitution Beach offers a generous size parking lot, water fountains, restrooms and snack bar. Piers Park has water fountain, restrooms and beautiful Boston harbor and skyline views. There are many people walking, biking and running this path and walking their dogs as well. There are emergency call boxes along the way and a couple of water fountains as well. The trail passes Bremen Street Park, Wood Island Train Station, a dog park, and the East Boston Library.

hiking
2 months ago

Educational and beautiful adventure along the roads of Boston. I live locally and decided to follow this path to explore parts of the city I haven't seen yet. It was fantastic and a great tour of Boston and her history.

Out to castle island with stops to play and get ice cream

Great views of the water and a bit of history with Fort Independence to walk around. There was a nice breeze off the ocean and it was s relaxing easy walk. If your timing is right, Sullivan’s has great lobster rolls and it’s located at the parking lot adjacent to the trail and the fort.

hiking
3 months ago

An easy hike throughout the city of Boston that was easy to follow. The Freedom Trail is easy to follow due to the red brick path that marks the trail.This trail is a great review of history and facts you may or may not have learned about the United States early beginnings. It was a great way to spend the day. We started in Charlestown at Bunker hill monument. The USS Constitution was a real highlight for me. The ship is incredible!

hiking
3 months ago

There are some beautiful, quiet spaces along this trail, intermixed with the heavily visited historic sites.

hiking
4 months ago

Beautiful views of Boston skyline. Paved trails for biking. Grefor birding.

We went for a relaxed and leisurely stroll around the pond. We parked at Olmstead park and walked down to Jamaica pond. Beautiful views, shady pathway, dogs on leashes, lots of geese with their younglings. Highly recommend for families and the elderly. Easy stroll. Boat rentals are also available.

hiking
bridge out
no shade
5 months ago

Great walk on a drizzly Boston day.

historical walk, parks, burying grounds, street performers.

hiking
no shade
6 months ago

Lots of doggos being walked. Beautiful view of Boston Harbor. Overall great walk. Perfect areas for a picnic.

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