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

views

birding

hiking

nature trips

kid friendly

wild flowers

trail running

dogs on leash

wildlife

road biking

dog friendly

beach

Boston, Massachusetts Map
VIEW FULL MAP
walking
2 hours 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
1 month 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
1 month ago

Great trail to see some historical sites!

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

walking
1 month ago

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

walking
1 month 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.

3 months ago

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
3 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!

Classic.

Very pleasant, why not?

walking
7 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.

7 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
7 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!

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

walking
7 months ago

This is just a spectacular trail. If you have read any of my other reviews, while doing city routes, I like to make these into a pub crawl. And the local Irish ☘️ has made this the best pub crawl/trail I have ever done. Yes, it was spectacular to see all of the history along the route, the only other place i’ve done a hike that had this much history and monuments is the National Mall in DC. The bars and food were amazing as well! The only thing that was a downer about this (which is my fault because I didn’t plan) is that I started this around 1600 and many of the places were closed. Because of this, I had to do some detours and could not see many of the churches, graveyards, and Paul Revere’s house. I’m just traveling through, so I do not think I’ll be able to do this again, but if I get a chance I certainly will.

walking
8 months ago

The Southwest Corridor Park is a 4.1 mile, linear park stretching from the Back Bay to Forest Hills. The park links South End, Back Bay, Roxbury and Jamaica Plain with a street-level, greenway. Recreational facilities include: 11 playgrounds, 2 spray pools, 7 basketball courts, 5 tennis courts, 2 street hockey rinks, 2 amphitheaters, and 6 miles of trails. A really nice way to connect the neighborhoods!

take the T.

trail running
10 months ago

I run this route regularly and love the ocean views. There were a few puddles along the route today that were leftover from (I'm guessing) a snowstorm that happened a few weeks ago. A lot of families will walk around this route when the weather is nice enough (e.g. today there were a lot of families and it was 45 degrees and sunny). I don't usually see wildflowers, but sometimes there are kite surfers (who can be carried maybe 20 feet up in the air) and Fort Independence is a cool place to visit too.

Nice walk around the parkway. Paved with some small hills but otherwise flat. No parking at the starting point. Will need to drive to the other side of the pond for street parking.

walking
Sunday, November 26, 2017

Pretty flat paved trail along the edge of the water. Parking lot has about 20 spaces. Beautiful views of the city.

Load More