Looking for the best trails around Ludlow?

Explore the best rated trails in Ludlow, 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 57 trails covering 521 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.

Air Line State Park Trail

Earth Day Tide

April, 2023 by optical21

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.

Find Nearby City trails

Accordion

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