Looking for the best trails around Milton?

Explore the best rated trails in Milton, MA, whether you're looking for an easy walking trail or a bike trail like the East Bay Bike Path (RI) and Mystic River Greenway . With more than 114 trails covering 675 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Groveland Community Trail

Some not so Good, Mostly very Good

April, 2026 by jim965

Starting at the Town Hall, the first half mile is on busy Route 113. There is a marked bike lane on both sides, but the sidewalk was not good for my recumbent trike and the road twists and turns, so visibility isn't great. I'll skip this part next time. At the half mile, Route 113 turns away and the trail goes along the river on a little traveled one way street. At a little over a mile, it's back on a two way street that has good visibility so it feels reasonably safe. As noted above, at 441 Main Street, the trail turns left onto a railroad roadbed, which is now a power line right of way, and continues southeast for almost two miles, with two road crossings. This is wide asphalt in excellent condition.

Although there are empty woods on the west side for much of the two miles, this is not a wilderness trail. I think there was at least one building in sight for the entire time.

In addition to parking at both ends mentioned above, there is parking at a National Grid facility at 452 Main Street, right at the head of the railroad trail.

Mayor James J. Fiorentini Bradford Rail Trail

Very Good, but too Short

April, 2026 by jim965

The trail is now wide asphalt in excellent condition, with clean, well groomed sides. Most of it is very close to the river, so, while foliage may obscure panoramic cross river views, it's still pleasant for a downtown trail.

Hanover Branch Rail Trail

Easy parking at Circuit Street.

April, 2026 by nadineklink

Park at Circuit Street for very easy access to historic sites. There are many interesting things to see at this end including the 1829 West Hanover Cemetery and beautiful water features at this end. Recommended.

Accordion

Topsfield Linear Common

Boxford piece short, but very good, Topsfield piece not good.

March, 2026 by jim965

First, be aware that the description is not accurate. The north end of this trail, from the dead end near I-95 to 2300 feet south of Pye Brook Road (PBR) is in Boxford, not Topsfield.

The portion north of PBR is a single rut, usable, but not great. From PBR south to the Boxford-Topsfield border it's a little over a yard wide, packed fine stone, not quite as firm as asphalt, but perfectly satisfactory for my trike. At the border, the trail becomes a single rough rocky track, barely usable and very uncomfortable on my trike. I can't comment further south, because I turned around.

Chelsea Greenway

trail

January, 2026 by haitaochen363

Good trail

Bruce Freeman Rail Trail

Great country ride, yet close to Urban life

November, 2025 by kleistikow

We’ve biked this many times. It quickly takes you from Lowell, with its National Park, etc to countryside and the center of small towns along smooth, paved, well-maintained trail. Nice to swim in Hart Pond, too, in season, on return trip to Lowell. Trail keeps getting better and better, great facilities along the way as trail is extended.

Washington Secondary Bike Path

Not a bad ride

October, 2025 by trainman1957

This trail needs open parking spaces! Most of the parking spots are blocked off!

East Bay Bike Path (RI)

Where is the bathroom if starting from Providence RI ?

October, 2025 by ningji

don't see bathroom in the parking lot

Salisbury Beach State Reservation Trail

large area lots to see.

October, 2025 by toddburrparts

Perfect place to ride for a beach day/ride. Explore the full state park and triple your mileage. A lot to see. And enjoy the ocean.

Deer Island Loop Trail

Neat little trail.

October, 2025 by chrismwy984

Nice short trail with beautiful views and an interesting history. If you’re biking, keep your mouth closed or you might ingest a fly in some spots.

Washington Secondary Bike Path

No e-bikes allowed

October, 2025 by dwxchcmrzk

This is a multi use bike trail for everyone to enjoy.

Upper Charles Trail

lots of street crossings

September, 2025 by chleary11

This is a good trail, but if you start in Milford and do the entire checkmark there are a lot of street crossings. The pretty parts of the trail are nice and shady and wooded, but there is a fair amount of commercial areas that you have to get through. It’s nice and flat and there are lots of parking areas along the way. My gps did not take me to a parking lot but when I put the trail into AllTrails I got accurate directions.

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Accordion

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