Looking for the best trails around South Hadley?

Explore the best rated trails in South Hadley, MA. Whether you're looking for an easy walking trail or a bike trail like the Appel Way Trail and Windsor River Trail . With more than 57 trails covering 524 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

Charter Oak Greenway

Not the best place to ride after 6.5 miles.

January, 2023 by darkstar826

If you ride longboard or inline skate. Get ready for terrible ground. if you start from Bolton State Park.. After 6.5 miles of riding... The ground is so mess up. There is so many cracks on the ground. Just be careful. Beside that, this trails has best downhill and cool turns.

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.

Accordion

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.

Harlem Valley Rail Trail

Rod it in sections

December, 2022 by bblhed_tl

I rode this over two separate weekends, Once from the Wassaic train station to Millerton, and once from Millerton to almost the end of the trail. Picking a favorite section is a really hard call, they both have their pluses. One of the things I really liked is the lack of level crossings making this more of a bikers trail than a walking trail with a lot of trail where you will only see bikes for a few miles. Pedestrians are great, with only bikes there is a lot less stress about passing. I think just about every level crossing has a portalet, even the ones without parking.

Wassaic didn't offer much in the way of attractions or close by food, Millerton on the other hand had plenty to offer and explore, there is even an actual bathroom on the trail in Millerton. While it would probably be fine to bike the town, I used the rack and walked it. Lots of interesting shops and food options in Millerton so it is worth stopping. Once you head north of Millerton you are back in open land with the occasional road crossings. There is a section where you ride over a large pond on a bridge that is nice.

Railroad Ramble

Nice but not exactly a "bike" trail.

December, 2022 by bblhed_tl

Walked this trail on 10/22/2022 and while it is a nice bike able trail, there are a few problems. I noticed that a few of the bridges are a couple of inches higher than the trail surface, and I'm not saying a little bump, I'm saying stop and walk it or fall off your bike bumps. Other than that this was a really nice trail and I would bike it with caution, or a mountain bike. Fall colors were amazing while I was there.

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.

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.

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Accordion

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