Looking for the best trails around Holyoke?

Explore the best rated trails in Holyoke, MA. Whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Mattabassett Trolley Trail . With more than 55 trails covering 527 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

Windsor River Trail

very nice and clean

November, 2022 by haseenarasool808

It’s beautiful good for kids nice and clean .

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.

Accordion

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.

Harlem Valley Rail Trail

Beautiful scenery along the route but some segments need maintenance

November, 2022 by earth2wayne

The Harlem Valley Trail from Taconic State Park to Wassaic (Metro North Station) spans 24 miles through beautiful farmland and marshy areas with Mountain ranges on both sides (Berkshire and Catskills). The entire trail is paved with asphalt. Unfortunately, there are older segments that sorely need maintenance, especially the roughly 4 mile stretch from Taconic State Park south. The trail is also narrow in spots making it uncomfortably close for bikes traveling in opposing directions. The trail does pass through several towns where you can find places to eat and shop.

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.

Farmington River Trail

very pretty

October, 2022 by lpusztai

We biked from Simsbury to Farmington on the Canal trail. It was nice with the fall color, but there is not much else to see. On the way back we took the River trail. It goes parallel to the river and it is very pretty. It goes thru Canton, which is a charming little town. From there the bike trail is quite good for a while, but then you have to bike on the road. The bike trail sign is painted on the road, but you have to look for it. Traffic was not bad at all. The last part goes thru a simsbury park, there are a lot of roots, gotta be careful. All in all the river trail is very nice, even with a couple of miles of in road biking. there there

Hop River State Park Trail

Wonderful!

October, 2022 by kate.decena

Beautiful for a bike ride in the fall. The trail is well kept, the views are beautiful and is moderately trafficked. I started at the Manchester trailhead and just kept going straight, passing parking lots in Vernon and Bolton. Didn’t notice much options for restrooms or pit stops for food so plan accordingly.

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.

Farmington Canal Heritage Trail

Very nice

October, 2022 by dcsnyder

Rode Plainville CT to CT/MA border. Northern section. I like that you go through many towns on the lower half then out in the country from Simsbury north. Beautiful scenery. Paved the whole way, some sections with roots coming through.

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Accordion

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