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 96 trails covering 739 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

Rockingham Recreational Rail Trail (Fremont Branch)

It's about summer OHRV

May, 2025 by fssn0wsh0e7

I've managed to ride portions of the trail between Fremont and Derry where it's open to summer OHRV on my hybrid bike (40mm gravel tires). It's not really pleasant as the trail is very sandy in sections to the point where I have had to walk my bike through sections. This is unfortunate because it's a great connector to the RT corridor that runs between Methuen, MA and Londonderry with the Rockingham Recreational trail from Manchester to Newfields. I get that summer OHRV use south of the North Woods is a scarce resource and that bikes do have the option of riding on the pavement. Except the shoulders of the roads are awful narrow. I could go on about the short sightedness of State and Local government but...

Rockingham Recreational Rail Trail (Portsmouth Branch)

Smooth level no hills, cider trail, good signage, full canopy. Recommend starting at South End near or at Hampton Airfield and at end of ride watch small planes and have lunch

May, 2025 by steve80

Smooth level no hills, cider trail, good signage, full canopy. Recommend starting at South End near or at Hampton Airfield and at end of ride watch small planes and have lunch

Southern New England Trunkline Trail

Correction

May, 2025 by arno911

...we rode the western part... (is there a tool to edit a review?)

Accordion

Southern New England Trunkline Trail

Partly very rough ride

May, 2025 by arno911

We rode the eastern part of the trail today, starting at the CT/MA border towards Douglas. The first 6-8 mls are well maintained and a good ride even with a street bike. Nice scenery, too. But then things get worse around Douglas. Rough surface with crushed stone, sand and deep puddles after a rainfall (like today). Looks like the track has not been maintained in a while and detoriates. A mountain bike is a big plus and highly recommended in some parts of the trail. Was a good ride though but do not expect a smooth one.

Northern Rail Trail

One of the best in the state

May, 2025 by fssn0wsh0e7

I've ridden this trail many times and it never disappoints. I have ridden all of it in sections and each one has it's own charm. In the Grafton-Canaan stretch it can feel remote even though the highway is nearby. The section from Boscawen to Andover always has folks on it though I have never found it too busy to enjoy. The save can be said for Lebanon out towards Canaan. There are services available along the way though it might require some road riding to access some of them. The Friends of the Northern Rail Trail group does a great job, is responsive to user comments and is working to address issues like toilet access. That being said there are long stretches where you have to be willing to use the bushes. It's absolutely a carry-in/carry-out situation so its a good idea to be prepared.

Rockingham Recreational Rail Trail (Fremont Branch)

Lovely for e-bikes

May, 2025 by alaskacantors

We are bike-packing across the country with e-bikes. A good rail trail is such a nice escape from the road traffic - this one was a delight. Mostly solid packed surface, smooth, a few muddy spots. Very scenic with a mix of woods and wetlands. Watch your head on the tunnels. Highly recommend!

Blackstone River Greenway

Stanley Woolen Mill in Uxbridge going North to Church Street

May, 2025 by andrix

This is described as a 3.5 mile section but we only went about half way to the dam from the Stanley Mill. It is passable on bikes but has roots and larger stones along the stone path. It's really more a walking trail. The farm mentioned in the description was an interesting side visit and had very nice bath & water facilities. However, for a great biking experience the 10 mile section starting at Woonsocket is paved and a far more pleasant ride.

Assabet River Rail Trail

glorious

May, 2025 by robertschless60

Just rode the trail south to the Sudbury line. The east west trail is finished to the west for another 8 miles. It connects to the Hudson Trail at the end.

Bobby Woodman Rail Trail

Could be even nicer

March, 2025 by fssn0wsh0e7

I did this as an extension of a ride down from Newport on the Sugar River Trail. I agree with the comment above about the section along Washington street by all the box stores where you are essentially riding on the verge of the highway. It doesn't seem like it would take much to fix that section up and make for a more seamless connection to the Sugar river trail. It would also be nice at the end of the trail in Claremont to give some indications to local services (food!).

Sugar River Trail

A great ride

March, 2025 by fssn0wsh0e7

Last ride of 2024 and was it super! I have a gravel bike so no real issues with the multi-use aspect of the trail as it was in pretty good shape though you could expect to have a difficult time with skinny tires or after a prolonged dry spell. Very scenic, perhaps the most scenic trail I have ridden on in NH. I tacked on the portion into Claremont to get in the mileage and the part that closely parallels the highway is a bit sketchy.

Squannacook River Rail Trail

Flat trail perfect for running

March, 2025 by heather.kyte

Ran on this trail in the winter and was great! Very comfortable for running :)

Mass Central Rail Trail

Ware to Gilbertville and Gilbertville to Wheelwright

November, 2024 by arno911

Rode the two sections of this beautiful trail today. From the parking spot in the middle of the Ware trail towards Gilbertville is a nice ride along the river. But a short one. Opposite the old factory the trail suddenly ends and there are handwritten signs "Stop, Don´t go further, Private property..." It would only take a few yards to reach the next road to travel on towards Gilbertville. No chance. Shame on you, property owners! (The trailmap shows a way through, but that might be an error?)

Okay, same way back and on to Route 32 past Gilbertville, where the next trailhead is waiting;-)
Smooth surface, well maintained and even good for kids bikes and flat all the way to Wheelwright. 3 nice old bridges. This is one is fully recommended! Absolutely worth it.

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Accordion

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