Looking for the best trails around Medway?

Explore the best rated trails in Medway, MA. Whether you're looking for an easy walking trail or a bike trail like the Spicket River Greenway and Bridge Street Bike Trail. With more than 101 trails covering 558 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

Reformatory Branch Trail

this could be a great bike trail, but….

March, 2023 by fuller5rgr8

….it’s muddy, uneven, full of potholes, and frankly, sometimes downright dangerous. It’s not exactly family-friendly. Maybe someday it will be connected to the neighboring Minuteman Bikeway? One can only hope.

Neponset River Greenway

perfect park

March, 2023 by emilyvl91

This park is huge and has a ton of space for any outdoor activity! I go for hikes here all the time, bring my kids and my dogs here, and we all love it! It’s clean and safe and has the longest trails!

Mass Central Rail Trail

Weston part not the best for rollerblading

February, 2023 by 7q2vdb7mbx

The pavement is decent, but there’s no marked center line. Biggest complaint is that the trail primarily goes downhill as you go east, and primarily uphill as you go west, so you’re going to hate one direction or the other. Decent views. Poor road-to-trail transitions with broken up pavement and sand which is a nightmare for in-line skates. Much prefer the Cochituate rail trail

Accordion

Cochituate Rail Trail

Good for a quick in-line skate if you’re somewhat experienced

February, 2023 by 7q2vdb7mbx

It’s relatively flat, very smooth, and a quick punchy trail to skate. There are a couple of bigger inclines (particularly a bridge that goes over Cochituate Rd) and a lot of road crossings, so I don’t recommend for first time skaters to do the whole trail. However, I learned to skate on sections of the trail and now do the whole thing in about 12 minutes, so if you take it slow you can use this trail for a long time.

Bruce Freeman Rail Trail

what a great trail!

February, 2023 by fuller5rgr8

Love riding on it. There’s some odd curves, like near the lumber yard, but the trail will be an even greater asset when the latest extensions are added. There are some amenities along the way, such as portable toilets, and there are coffee shops and convenience stores on the way, too.

Twin Cities Rail Trail

walking.

February, 2023 by caddydvr

Love this rail trail !! Nice easy path , street crossings are easy to get thru. Great job by both cities.

Independence Greenway

Needs Two Critical, but Expensive Links

January, 2023 by robert.atkinson4

I grew up in this area, and while the trail offers great views and an easy ride, two (2) huge barriers make this trail incomplete. The trail needs to cross US Route 1 and MA Route 128 to really be complete. Crossing Route 1 would link this trail to the Border-to-Boston Trail and crossing Route 128 at the Northshore Mall would allow the trail to continue into Downtown Peabody at Peabody Square and link to trails in Salem and points North. Both crossings used to have train tracks crossing the highways, but in both cases, the tracks across the highway were removed long before the trails themselves were built (the rail line was finally decommissioned in the 1980's, after an elderly driver was killed trying to beat the train as it crossed Route 1). Building the crossings would require constructing bridges to carry the highways over the trails, and require redesigning the adjacent interchanges (Lowell Street and Route 1, also Route 128 and Lowell Street) with the highways, a considerable expense that would cost tens of millions of dollars. The upside is that both interchanges are in desperate need of an overhaul, with traffic backups onto the highways at rush hour and stop signs at the tops of the ramps that merge onto the highways. That might have been acceptable in the 1940's, when these roads were built, but is intolerable now, with today's high traffic volumes.

Ware River Rail-Trail

Great if you like exploring, like I do.

January, 2023 by alan113

Rode (7/22) from Winchendon to Baldwinville, and then (skipping the part bisected by Rt. 2) from from Rt. 101 in Templeton to Route 122 in Smithville on the Barre/Oakham line. Lots of wet and rutty sections north of Balwinville but still fun (some walking with 1.5" tires). Some sandy section in the southern piece but still fun. It's slow going of course. Didn't pass a single extra person. Good roadside fried food at Lee's in Baldwinville (it's been there for at least 70 years!)

Grand Trunk Trail

Map Update Grand Trunk Trail - Sturbridge, MA section

January, 2023 by bouvier90

Updates needed for map. Past the Ed Calcutt bridge, the trail spur to River Road is closed as private property. However the main trail has been completed along the river to Farquhar Road, adding about a mile to the existing trail. From the Farquhar Road exit you can take a left on the roadway to reach River Road.

Nashua River Rail Trail

Caution needed with leaves on the ground - hard to see the shoulder/gully on the side.

November, 2022 by ccoakle

My friend and I, both experienced riders, had a nice time on this trails today until we didn't With leaves on the ground, the shoulders on both sides of the trail are obscured. The paved trail is likely 3-4 inches higher than the shoulder. A few times heading north, we rode behind each other and to the right to create space of people coming towards us. We were several yards shy of parking lot at Gilson St when my friend moved right to make space. Obscured by piled up leaves, she could not appreciate where the the pavement ended and the shoulder dropped off. She corrected back onto the path, but not before her tires slipped on the leaves, and she suddenly lost control of the bike. She fell to the ground. I was behind her. Given the way she fell across the path, I couldn't avoid her, Two of us were now on the ground, bikes, too. I am grateful to the folks who stopped to help and show concern for our well-being. I am so very grateful to the gentleman, Tom, who took me back to my car in Ayer so I could come back and pick up my friend and our bikes, delaying his own cycling.. Thanks to the man who helped my put my friend's bike in my car. My friend is undergoing a medical evaluation to determine the extent of her injuries to her back, flank, and hip. Thankfully she was wearing a helmet when she struck the back of her head on the pavement.

Minuteman Commuter Bikeway

Great day!

October, 2022 by dianesirvydas

Beautiful historic bike trail…well maintained…perfect fall day activity! Will do again!

Northern Strand Community Trail

Finished from Lynn to Everett

October, 2022 by rfrenkel123

There are older reviews on here from 2021 and before. Now the trail has been completely finished (paved) from Lynn to Everett and only one small section remains to be paved that extends it to the Encore Casino area at the southern end. The views are fantastic of both the Rumney and Saugus marshes and its often hard to believe you're biking through highly built up areas. I usually bring my bike by car to near Market Basket in Lynn to start.

Find Nearby City trails

Accordion

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.