Looking for the best trails around Rockingham?

Explore the best rated trails in Rockingham, VT. Whether you're looking for an easy walking trail or a bike trail like the Stevens Rail Trail and Warner Rail Trail and Bagley Rail Trail. With more than 40 trails covering 316 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

Ashuwillticook Rail Trail

Excellent ride- one of the best trails!

November, 2022 by billmeredith58

We rode the Ashuwillticook Trail on 11/07/22 from the Pittsfield trailhead to Adams and back. The ride is excellent, with plenty of scenic highlights along the entire route, smooth paved surface and many places to stop and enjoy. The towns along the route looked inviting enough to divert us, but we had time constraints so we stayed on the route. The head winds on the way back were a challenge..
This is one of the best trails we have been on, not to be missed.
PS Recommend enjoying a long weekend and stayed at a B+B in Lenox...

Note: the restrooms along the route were all closed. I can understand given the time of year but it seemed somewhat premature given the warm weather we had been experiencing.

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.

Accordion

Ashuwillticook Rail Trail

Beautiful Trail

October, 2022 by lexonyskiddiecollege

We decided to go when the leaves were just starting to change color and fall. What a great time to go. So many awesome photos we were able to take. The trail is such a relaxing place to enjoy the outdoors. We were only able to do the first section from Crane Ave to the Berkshire Mall entrance. Took us about an hour to leisurely walk that distance before it started to get dark and we had to turn back around. I’m hoping they will decide to put some kind of lighting through out the trail. Otherwise, it’s nice and clean, pet friendly and plenty of spots to rest and take the scenery in and get a few photos. I feel like we will enjoy this trail more now that the crane Ave part is completed.

Ashuwillticook Rail Trail

Beautiful Trail

October, 2022 by lexonyskiddiecollege

We decided to go when the leaves were just starting to change color and fall. What a great time to go. So many awesome photos we were able to take. The trail is such a relaxing place to enjoy the outdoors. We were only able to do the first section from Crane Ave to the Berkshire Mall entrance. Took us about an hour to leisurely walk that distance before it started to get dark and we had to turn back around. I’m hoping they will decide to put some kind of lighting through out the trail. Otherwise, it’s nice and clean, pet friendly and plenty of spots to rest and take the scenery in and get a few photos. I feel like we will enjoy this trail more now that the crane Ave part is completed.

Ashuwillticook Rail Trail

Gorgeous fall color ride

October, 2022 by enlowe12

I started at the trail head at Crane ave in Pittsfield and rode the 13+ miles to Adams and back. It is possibly the best trail I have ridden. Paved, well maintained, no roots causing bumps in the pavement. Within 1/4 mile of the start I was out of the industrial area and into wetlands and beautiful scenery. The trail goes along three reservoirs in the 13 miles. There are plenty of places to park and jump on the trail, and also rest rooms along the length. Definitely recommend this trail.

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.

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.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Cheshire Rail Trail (South Portion)

October, 2022 by gail glines

I rode from near the Massachusetts state line and Rt. 12 north to Keene, NH on 10/01/2022 using a cyclocross bike with mid-width knobby trail-riding tires. The conditions were very good in general but, in the portion where it reduces to a single track in width you often needed to dodge rocks sticking up in the path. The portion of this trail with several deep cuts through the rock hills are quite a memorable sight to see. Take care crossing the stone arch bridge because there are no guardrails. Overall this was an enjoyable trail to ride.

Valley Trail

great quiet walk

September, 2022 by dclippa

This is a lovely, easy , quiet walk. Much improved from a few years ago, based on the reviews. Great for families, dogs and their humans.

Ashuwillticook Rail Trail

August 2022 Best Trail Ever

September, 2022 by g244dpz8y7

It took me 3 hours from Nashua NH to drive to this trail and it was completely worth it!!! As of 2022 I rode this trail from beginning to end and did not find a single bump, frost heave or pot hole, the smoothest paved trail I have ever been on. Then there is the scenery which is just spectacular and when fall comes the foliage in the Berkshires is going to be just great. The only issue I had was there was no parking at the trail terminus in North Adams, I parked on a city street there is parking directly on the other end in Pittsfield.

Ashuwillticook Rail Trail

If only every trail was this nice!

September, 2022 by eajack

I want to take stars away from other trails to give this one an 8 out of 5, that's how nice it is! We rode this end-to-end and every inch of it is wide and smooth, with beautiful wooded surroundings, lakeside vistas, or quaint small town vibe (the Adams end.) If I had to find something to nitpick, it would have to be that we found the public restrooms on the north end to be closed when we desperately needed them. It was about 6pm on a Saturday at the time. But the fact that there are true restrooms (not porta-potties) on the north and south ends of the trail is a vast improvement over other trails we've been on.

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