Explore the best rated trails in Winchester, 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 574 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.
….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.
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!
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.
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.
Love this rail trail !! Nice easy path , street crossings are easy to get thru. Great job by both cities.
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.
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!)
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
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.
Beautiful historic bike trail…well maintained…perfect fall day activity! Will do again!
Very nice & flat trail. Well kept and pretty scenery...'specially in the fall.
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