Looking for the best trails around Winchendon?

Explore the best rated trails in Winchendon, MA. Whether you're looking for an easy walking trail or a bike trail like the Warner Rail Trail and Bagley Rail Trail and Sugar River Trail. With more than 90 trails covering 669 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.

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

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.

Accordion

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.

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.

Connecticut Riverwalk and Bikeway

Sometimes getting there is fun as well

December, 2022 by bblhed_tl

I rode the Northern section of the trail, (the section north of rt 5 and on the east side of the river) so this review is about that, and how I got there. The trail appears to be nice and well maintained, it is in a larger city so it does have some city issues, but I always felt safe. Views are mostly of the Connecticut river and the rail line, Basketball hall of fame doesn't really look great from the trail, and the park along the trail is less interesting than the river itself. If you like looking at railway infrastructure that is still in use this trail will not disappoint either.

I used the Springfield train station to get food, drinks, and use the restroom, there was enough room to easily get my bike into the bathroom.

I took the Hartford line train from Wallingford CT to get to Springfield and I was really happy about how easy it was to do that, YMMV as CT line staff are being lazy and not opening the bike rack doors on some trains. I did this trail mostly to see how easy it is to take the train to the trail and I was happy with that part of the trip.

Canalside Rail Trail

Bonus! Bonus!

November, 2022 by egauger

Nice trail, what it lacks in length it makes up for in bonuses. 1. Brick and Feather Brewery along the path with outdoor seating. 2. Discovery Center Museum near trailhead in Turner’s Falls, free, cool animal displays and lots of interesting information in this little gem.

Fort Hill Recreational Rail Trail

I agree with previous reviews

November, 2022 by slasalle76

After riding the Ashuelot Rail Trail in the summer and seeing this from the parking lot on Rt 63, I came back on an unusually warm November weekend to give it a try. I fully concur - this could be a gem of a trail if a bit more work could put in, but still a nice enough ride. I was on my hybrid, and am beginning to wish for a Fat Tire or maybe at least a shock absorbing front fork for these jouncy pot-holey trails. Pity that the trestle is falling to ruin, and in the slight rain I was caught in, I didn't chance it with slippery sneakers. Frankly, it's a tragedy waiting to happen, and with as many rotted rails as there are, I was surprised to see 3 bikers walking gingerly across. Kudos to the snowmobile clubs who watch over this trail, as you could see where chainsaw work had been done to keep it open.

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!

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Accordion

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