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Explore the best rated trails in Westfield, 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 53 trails covering 483 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.
Road part of this trail as an out and back in conjunction with the Southwick RT and the Columbia Greenway RT from Avon, CT, to Westfield, MA, an approximately 50 mile round trip (25 on the Farmington Canal Trail).
The trail is in very good condition. The transition to the Southwick Trail at the CT/MA border (with no road crossing) is seamless.
Road crossings decrease as you head north and are well marked with push-button warning signals to alert traffic.
Half Mile Falls Park at the north end of the Columbia Trail in Westfield is definitely worth a stop!
Road this trail as an out and back in conjunction with the Farmington Canal Heritage Trail and the Columbia Greenway RT from Avon, CT, to Westfield, MA, an approximately 50 mile round trip.
The trail is in excellent condition. The transitions to the Farmington Canal Trail at the CT/MA border (with no road crossing) and to the Columbia Greenway RT on the north are seamless.
The mileage markers are great!
Half Mile Falls Park at the north end of the Columbia Trail is definitely worth a stop!
Road part this trail as an out and back in conjunction with the Southwick RT and the Columbia Greenway RT from Avon, CT, to Westfield, MA, an approximately 50 mile round trip.
This trail should be a 5 but it is closed at Main Street in Westfield with no information on when it will reopen or detours.
I got onto the trail at Southbury. I parked at IBM since there was no parking at the trailhead, and got a nice (?) note from security on my windshield. The first half mile from Southbury is very verdant and marked by nice wild phlox, but the path was so narrow you had to watch your feet instead to try to avoid the poison ivy. It widens out once you get to the rail trail. We saw a heron and a deer. A woman on horseback said the heron is famous for trying to scare the horses, they call it the "Pterodactyl". The trail seems to disappear once you get to some of the cross roads and is hard to find again.
I just rode this trail, again. I pleasantly surprise that the trail has been extended about 3/4 mile and now goes up to motor vehicle office in Winsted.
Really liked this well maintained trail. Great views with picnic tables along the route. Wish is was longer.
We started in Douglas, MA, at the parking lot on Rt 12/South St and road westward. The SNETT connects to the Airline trail in E Thompson. We finished at a parking lot on Rt 12/Riverside Rd in Thompson, CT, just south of Acme pond. Round trip was 22.5 miles.
The trail in MA is a mix of conditions and needs some grooming. Still some shallow puddles and wet spots, but all rideable. I recommend a gravel bike or mountain bike, something with at least 45mm tires (my bike). My wife road a hard tail mountain bike with 2.20in tires and had no problems. A front shock is a plus, as the trail had occasional rocky stretches, and a shock will help in those parts.
The trail in CT is in good shape, groomed, and smooth. A mountain bike is not needed on this stretch of the trail, but a bike with 30mm tires or less would not be a good idea for the average rider.
Was not expecting trail to be as nice as it was. Rode from southern trailhead to Millerton about 12 miles one way. Great views of farms / hills / streams/ wetlands all along a nicely paved trail. Planning to go back and complete the remaining 13 miles north of Millerton. And by the way thank you to Millerton for the excellent bathroom facilities!
Nice cool day to ride from the Chaplin area up to Putnam. Beautiful country with few other folks. 16 miles each way. Trail was in good shape with just a few wet areas. Some nice newer bridges and tunnel for bigger road crossings. A few areas with larger gravel. Easy to go from trial into Putnam for food. Also a nice bike shop in Putnam.
Beautiful trail except for the person that doesn’t clean up from horse riding on the trail.
There are no curves or bends in this section. Just a straight line. There is a dirt track in the middle. For the kids there are signs with questions which is nice
It’s a beautiful trail. BUT, please beware of the yellow post they have installed at all the road crossings to keep motor vehicles off the trail. As I was crossing the road at one of the crossings, as I came back onto the trail my handlebar caught the post and sandwiched me in my bike and the bike and I went down hard. I ended up fracturing my back. So please be careful on this trail through Southwick.
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