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

walking

kid friendly

views

nature trips

bird watching

wild flowers

hiking

trail running

dogs on leash

wildlife

road biking

dog friendly

beach

city walk

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hiking
no shade
13 days ago

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

hiking
18 days ago

June 2018, busy but so much fun

hiking
21 days ago

Great guided tour

We did this hike as a part of a group tour. In hindsight, we should’ve done it on our own or had a private tour. The group tour dynamic did not go too well. The private tours should be booked two weeks in advance to make sure that there is availability.

Awesome hike for history buffs.

hiking
3 months ago

Excellent hiking inside the city! It's rare case when you don't need your hiking boots to have a great hike! ;) There are a lot of great historical places which will be faced on this trail. Nice trail!

walking
4 months ago

Very easy. Surface is a little bumpy in spots, but it is a nice walk in the fall.

Boston is so rich in the history of our nation and an excellent place to visit with the children. There is so much to explore!

on Jamaica Pond

walking
5 months ago

Jamaica Pond is a pretty and easy walk, especially in the fall. The trail around the pond is paved and relatively level. There is a small parking lot for the park on Willow Pond Road as well.

hiking
5 months ago

Great trail to see some historical sites!

walking
5 months ago

Excellent experience if you love history. Even if you are not a history buff this pathway is great for sightseeing.

walking
5 months ago

Easy trail, pretty views. You do walk around a huge water treatment plant, but it didn’t bother me.

walking
5 months ago

I enjoyed the walk and the landscape was pretty on a fall day. The main paths are paved and there are a few smaller trails throughout the route that are unpaved but cleared. I had not walked there before and it was worth the trip.

Stunning views of Boston skyline.

A very nice way to get acquainted with the city when you are there for the first time. We all enjoyed it, including our 8-year-old son.

This is a must do when going to the Boston area. It’s full of history and and wonderful hike through Boston. We elected to use a tour guide and it made it so much richer.

A great family hike around Boston! Food options were delicious; gotta check out Quincy Market. Love Boston culture and its history.

hiking
8 months ago

This trail would is quite scenic especially at night. The view of Boston's skyline is really spectacular from here as I've caught it several times now.

The major problem with this trail is that from time to time, the smell coming out of the sewage treatment is pretty strong. It's not constant so you may smell it or you may not on a given hike. If not for that, this trail would be so much nicer.

This is by far my favorite trail in the Boston area especially for evening walk. The sunset view from here is simply sublime and the views is unbeatable. And on windy days you are treated to wind surfers doing stunts on the bay. There is a nice children's playground and a really cool clam shack called Sullivan. I also enjoy watching planes go by at really close level from here.

And from the pier you can see all kinds of boats go in and out of the harbor. I enjoy watching those dinner or party boat cruise go by. The only minus is that it gets much windier than anywhere else in Boston.

Cute

Great time. Easy walk with plenty to see.

I was in Boston for a conference and looking for a nice, easy trail to ride a rented bicycle. This was a perfect little excursion. It was very easy to get to, the trail is paved, and there are accessible beach areas. There are also public restrooms and a snack bar. Very nice!

hiking
10 months ago

Classic.

Very pleasant, why not?

walking
11 months ago

Nice easy walk around the island. Yes, it can smell at certain points, but it’s not the entire walk. It was overcast today but still beautiful. Gorgeous Boston city skyline. Easy walk for the dogs with paved trail the entire way. Small parking lot. Would love to come back with sunny skies.

11 months ago

Great trail for walking, running, or just relaxing for a moment on one of the benches. Jamaica Pond is beautiful in the spring when the trees bloom and good for watching some of the waterfowl. Very dog friendly trail as well - you’ll see lots of puppies, runners, and families.

walking
11 months ago

can't believe I spent most of my life hearing about this place but hadn't visited. I really like it... water views, city views. nice place to picnic. play area for kids. paved paths. watch plane activity at Logan.

best views of the boston skyline at the top of north drumlin! great little hike. love the harbor islands so much!

hiking
11 months ago

An absolutely wonderful way to see Boston and learn a lot of history!

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