Looking for the best trails around Southborough?

Explore the best rated trails in Southborough, MA. Whether you're looking for an easy walking trail or a bike trail like the Common Pathway and Spicket River Greenway. With more than 113 trails covering 639 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

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.

Accordion

Old Eastern Marsh Trail

old eastern marsh trail

November, 2022 by rickfragala

We rode it today 11/10/22, it was a 70 degree sunny November day. My son, who is disabled and I rode a tandem recumbent bike. We are trying to complete all the rail trails in New England. I have to say this was one of the most beautiful trails up to this point. The scenery changed all the time, from woods to marshlands to the Merrimack River. We will definitely do it again

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!

Monadnock Recreational Rail Trail

Very nice & flat trail. Well kept and pretty scenery...'specially in the fall.

October, 2022 by kentherrien_tl

Very nice & flat trail. Well kept and pretty scenery...'specially in the fall.

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.

Common Pathway

Mostly Bike

October, 2022 by mbdsvn6q9d

Too urban to be considered a hike or bike; winds along community roads along river. Not a hike.

Tri-Community Greenway

fun ride

October, 2022 by smholsing

Great local trail. Well done and maintained. Only negative is the number of road crossings. If you are looking for a quick close to home trail this is a good trail.

Narrow-Gauge Rail-Trail

quiet trails with a few road crossings

October, 2022 by jamesss36

Overall not heavy usage on a Saturday afternoon in September. Parking is easy. Southern sections have a few road crossings at the end. The northern section is not as well maintained.

Watertown-Cambridge Greenway

Great connector trail

October, 2022 by rickcontix

It might not be long and the Watertown end is developing some nasty root bumps, but it's a fantastic way to connect from the 'burbs to Boston. Now that it's finally finished, I can ride from Bedford to downtown Boston (via Minuteman and Charles River paths, etc.) virtually all off road. So glad it's complete!

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Accordion

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