Looking for the best trails around Williamstown?

Explore the best rated trails in Williamstown, MA, whether you're looking for an easy walking trail or a bike trail like the Spring Run Trail and Zim Smith Mid-County Trail . With more than 46 trails covering 708 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

Canalside Rail Trail

You can expand your ride…..

March, 2024 by basil1986

I love this trail! Rode it on 3/14/24 when weather was 62 degrees. This trail is short but can be expanded if you cross the metal bridge by the brewery and take the road to the left leading to the Fish Research Hatchery on the opposite side of the canal. If you meander through the little neighborhood on that side as well you can extend it further and get another view of the old mill complexes. I get 20 miles out of the ride. Bring a lunch there are picnic tables on both sides!

Columbia Greenway Rail Trail

A gem of Westfield and the region

March, 2024 by jmchatton

The Columbia Greenway Rail Trail is a beautiful rail trail that has a little of everything. City views, farmland, rivers, and tree cover in just 3 miles. The bridges are also a feature that make this trail unique. I love that it connects to trails that go much further south into CT, so whether you are just going for a short walk or a long ride you can do it here! Plenty of access points too (including 4 in downtown Westfield alone) make it easy to get on the trail from nearby neighborhoods or get off to shop and eat at downtown businesses.

Ashuwillticook Rail Trail

Not ADA compliant

February, 2024 by ljt trike rider

It looked very nice from the parking area, but could not get through the barricades with a recumbent trike. Drove over an hour and gates were shut and would have had to lift trike over gates. Disgusted with Massachusetts and whomever designed the barricades. Has anyone heard of the ADA?

Accordion

Ashuwillticook Rail Trail

Great fall ride.

November, 2023 by cantabty

Excellent experience on this fresh paved trail. The scenery of the ponds and mountains in the distance was worth the trip.

Harlem Valley Rail Trail

flat . smooth. gorgeous

October, 2023 by lindarkv

I rode the southern half of this trail from Millerton to Wasaic the first week in October on a 75° afternoon. Beautiful ride on a beautiful day.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

We found the Trail notTrail not as described

October, 2023 by luvaneezer

Cheshire Trail South. Rode north from State Line Circle toward Kenne. We are experienced road cyclists, now riding gravel bikes. We are looking for reasonably surfaced longer trails and hoped this would be one of them. Sadly, we found this trail to be rocky, rutted, with lots of roots, and uncleared blowdown. The vigilance required to remain upright made it difficult to enjoy the beauty all around. The suddenly occurring steep inclines to roads seemed borderline dangerous. If we lived closer it would be a great trail to walk with the dogs

Erie Canalway Trail

Medina NY to Gasport NY

September, 2023 by mconlon1

About a 45 minute ride on the Erie Canal path ,starting at the Medina lift bridge, through farmland and villages (Middleport, Gasport) herons that are absolutely not afraid of you! Beautiful in the fall!

Delaware and Hudson Rail-Trail

dog warning

September, 2023 by guamlee7

just walked the D & H trail from granville center to middle granville. really enjoyed the walk out toward middle granville but on the way back while walking through the farm (which was a delightful experience on the first trip through, seeing calves and cows) but then were charged by two pitties which attacked my dog and knocked me down. Luckily I had an umbrella and was able to get up and get away and down the trail. the dogs followed for a while but then returned to the farm. Too bad because was a very enjoyable walk until this. I just hope these two dogs dont really hurt someone....

Ashuelot Recreational Rail Trail

Still a lovely ride in spite of washouts

September, 2023 by nanlovell77

I would hate for people to avoid this lovely trail because of reports of the washouts. By using the trail map from this app or even Google maps you can easily find nearby roads that allow you to ride around the closed sections. We had a lovely 18.7 mi ride today and we’re able to keep cool because of lots of shade even though it got up to 90 degrees! They were repairing the bridge on the road to the Slate Covered Bridge, but they paused work to let us cross. It will be repaired very soon.

Harlem Valley Rail Trail

Serene and lovely

September, 2023 by raresparky

Rode the 13 miles from Orphan Farm Rd to Millerton and back. At the northern end, at Orphan Farm Rd is a large parking area adjacent to a small farm, a solar panel field and a glamping site. No one there at 8am that Saturday but half a dozen cars upon my return at 11. Likewise, I had the trail practically to myself until I neared Millerton and found it moderately traveled by later that morning. The asphalt trail was in very good condition and there are a few boardwalk sections as well, also in very good condition. The environs are beautiful with forested sections, farm fields, wetlands and vistas of the nearby hills. Not more than two miles from the north end is the Depot Deli, near the entrance to Taconic State Park, where all manner of beverages, ice cream and snacks can be found. Breakfast at Oakhurst Diner in Millerton is highly recommended. Clean public bathrooms can be found just behind the schoolhouse museum beside the trail after crossing the main street.

Ashuwillticook Rail Trail

Good scenic ride

September, 2023 by richmedcraft

I rode the trail from Pittsfield to the end in North Adams and back on 8/5/23. The trail is paved and in good condition and restrooms at the Pittsfield trail head were clean and working fine. Nice scenery including lakes and the Berkshires- I was able to finally identify Mt Greylock after the morning clouds had dissipated. The grade is gentle and I was able to keep up a consistent pace for the ride.

Ashuwillticook Rail Trail

great trail

September, 2023 by dpwrztjhrw

Asphalt smooth and trail is terrific. Easy, flat trail with some water views passing Silver Lake/Pittsfield.

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Accordion

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