Looking for the best trails around Wilbraham?

Explore the best rated trails in Wilbraham, MA. Whether you're looking for an easy walking trail or a bike trail like the Upper Charles Trail and Windsor River Trail . With more than 58 trails covering 526 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

John & Lisa

June, 2023 by handyj418

June 2023
This trail is second to none! Rode from Lanesboro to Adams-- flat, clean great scenery. Many turtles, water birds, and spotted a deer. Considering a return in the fall as I am sure the color is amazing.

Hop River State Park Trail

Hop River

June, 2023 by trainman1957

Starts off a little rough! Then it is one of the best trails around!!!

Cheney Rail Trail

great biking trail

June, 2023 by trainman1957

This trail was a lot of fun! Very easy to pedal on it!!!

Accordion

Ashuwillticook Rail Trail

Great trail in MA!

June, 2023 by steve.schwinn

Road the trail last week end-to-end as an out and back from the great southern trailhead parking area on Crane Avenue (bathroom). Trail is in excellent condition and a great ride.

Farmington Canal Heritage Trail

Combination trail ride into MA

May, 2023 by steve.schwinn

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!

Southwick Rail Trail

Great trail with seamless trail connections at both ends!

May, 2023 by steve.schwinn

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!

Columbia Greenway Rail Trail

Trail closure

May, 2023 by steve.schwinn

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.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Beautiful section in terms of scenery and access to lakes and ponds. The surface can be challenging. Today, with fairly dry conditions, it could be negotiated with hybrid bikes.

May, 2023 by earthman58

Beautiful section in terms of scenery and access to lakes and ponds. The surface can be challenging. Today, with fairly dry conditions, it could be negotiated with hybrid bikes.

Sue Grossman Still River Greenway

Trail has been extended

May, 2023 by colleen727

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.

Windsor River Trail

Really liked this well maintained trail. Great views with picnic tables along the route. Wish is was longer.

May, 2023 by a19olsen

Really liked this well maintained trail. Great views with picnic tables along the route. Wish is was longer.

Southern New England Trunkline Trail

Douglas, MA to Thompson, CT

May, 2023 by aplennon

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.

Washington Secondary Bike Path

Rollerblading? See here....

May, 2023 by mark565

This was my first time at this trail. I took the reviews to heart
and chose to park at the Horgan Elementary School lot (near
some Tennis Courts and the Red Caboose!).

Despite out-of-state plates, I had no challenges parking. No stickers or anything were required and
the parking area felt safe.

I chose to Rollerblade on the trail WEST to the End in Coventry.

The first 2 to 2.5 miles are not-so-pretty. It is very urban...some "small" tent out-croppings
along the right-hand bank of the river -- and very industrial....

I kinda wondered why I was there (though felt safe).

The pavement had some bubbly spots and the wooden bridges are a bit course on Rollerblades (keep your momentum up and you can get right across them...or stop fully and take in the views...)

But after you get past the "urban" areas...the trail West toward Coventry REALLY begins to shine. It does have a gradual upward slope most of the way, but seriously quite doable. The quality of the pavement gets better and better and there was only very minor debris on the path. A VERY good path to Rollerblade!

I chose to Rollerblade on the RIGHT side going in both directions, so as to not have to square off with any fast moving bikes. Everyone on the path was VERY warm and courteous!

The major part of the path through Coventry is truly gorgeous...and well worth the ride!

I confirmed with MANY bikers that the stretch EASTWARD to Cranston is NOT suitable for Rollerbladers...Many of the bikers said that it even stinks for bikes actually!

So, the segment from the Horgan Elementary School to Coventry (sort of going "RIGHT" on the trail if tennis courts are behind you) is the place to go!

Couple more things:

There do appear to be some VERY nice parking areas a bit further into Coventry and one MIGHT be able to skip the first 2-2.5 miles of the trail and park just a tad bit closer toward Coventry....That 2-2.5 miles is kinda "crummy", so you're really not missing anything. I don't know the names of those parking areas -- but did not see any signs saying "Residents Only" or anything.

Also, the GENERAL STORE at the very far end of the trail in Coventry is no longer open...so don't plan on getting water or anything there. There ARE a few gas stations one can see along the trail and the very cute ice-cream shop that many have mentioned, as well!

Lastly -- the trail does end very suddenly, when you reach the end in Coventry and there is a Map/Sign that seems to imply that the trail continues into Connecticut....That apparently is NOT true "yet"...but is being planned.

When you look on the backside of the Granite Mile Markers (heading West), they will IMPLY that that you have like 4 or 5 miles MORE to go, but you will hit the END of the trail at around Mile Marker 4.7 -- so it appears that they FUTURE proofed the Mile Markers and included the distance that WOULD be there if the trail did continue into Connecticut.

Several bikers said that one COULD continue into Connecticut via the very busy looking road. I chose not to, being on Rollerblades.

If you are close to Coventry -- start at the Coventry end and blade/bike/walk/run all the way toward the other end -- and simply stop and turn around when it starts to get "uglier"...the final very, very large wooden bridge may be a place to stop and turn around.

Anyway -- it was a GREAT experience...but that first 2 - 2.5 miles from the Horgan School West toward Coventry is a tragic sort of area...the trail itself is okay, but as you head West, you will see what the 5-Stars are all about!!

Enjoy!

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Accordion

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