Greenfield, MA Bike Trails and Maps

960 Reviews

Looking for the best Bike trails around Greenfield?

Find the top rated bike trails in Greenfield, whether you're looking for an easy short bike trail or a long bike trail, you'll find what you're looking for. Click on a bike trail below to find trail descriptions, trail maps, photos, and reviews.

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Length
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34 Results
Activities
Length
Surfaces
Type

Ashuwillticook Rail Trail

13.9 mi
State: MA
Asphalt

Blackstone River Greenway

31.6 mi
State: MA, RI
Asphalt, Boardwalk, Crushed Stone, Dirt

Bloomfield Greenway Multi-Use Trail

1.8 mi
State: CT
Asphalt

Canalside Rail Trail

3.6 mi
State: MA
Asphalt

Columbia Greenway Rail Trail

3.1 mi
State: MA
Asphalt

Farmington Canal Heritage Trail

49.1 mi
State: CT
Asphalt

Jonathan Daniels Trail

0.9 mi
State: NH
Crushed Stone

Keene Industrial Heritage Trail

1 mi
State: NH
Asphalt

Manhan Rail Trail

9.5 mi
State: MA
Asphalt

Mass Central Rail Trail

64 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Quinebaug Valley Rail Trail

5.7 mi
State: MA
Ballast, Cinder, Dirt, Grass

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

South Spencer Rail Trail

1.62 mi
State: MA
Crushed Stone

Southwick Rail Trail

6.5 mi
State: MA
Asphalt

Westville Lake Community Trail

0.7 mi
State: MA
Crushed Stone

Ashuelot Recreational Rail Trail

21.4 mi
State: NH
Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Common Pathway

5.5 mi
State: NH
Asphalt, Crushed Stone

Connecticut Riverwalk and Bikeway

7.8 mi
State: MA
Asphalt

Fort Hill Recreational Rail Trail

7 mi
State: NH
Ballast, Cinder, Dirt, Gravel, Sand
Accordion

North Central Pathway

11.2 mi
State: MA
Asphalt

Old Railroad Trail (NH)

2.7 mi
State: NH
Dirt

Potanipo Rail Trail (NH)

2.7 mi
State: NH
Crushed Stone, Gravel

Rocky Hill Trail

0.9 mi
State: MA
Asphalt

Squannacook River Rail Trail

3.7 mi
State: MA
Crushed Stone

Toonerville Rail-Trail

3.2 mi
State: VT
Asphalt

Twin Cities Rail Trail

4 mi
State: MA
Asphalt

Brookline Rail Trail

4.5 mi
State: NH
Crushed Stone, Gravel

Chicopee River Canal Rail Trail

0.21 mi
State: MA
Asphalt

Granite Town Rail-Trail

3 mi
State: NH
Ballast, Cinder, Dirt, Grass, Gravel, Sand

Valley Trail

9.1 mi
State: VT
Asphalt, Dirt, Gravel

Appel Way Trail

1.3 mi
State: NH
Asphalt

Bennington Rail Trail

1.65 mi
State: VT
Asphalt, Crushed Stone, Gravel
Trail Image Trail Name States Length Surface Rating
Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along a 13.7-mile paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through the Hoosic...
MA 13.9 mi Asphalt
Throughout history, the Blackstone River has been an important waterway, from its use by American Indians who fished its once-abundant salmon to its role as a major artery for the transportation of...
MA, RI 31.6 mi Asphalt, Boardwalk, Crushed Stone, Dirt
The Bloomfield Greenway Multi-Use Trail currently runs 1.8 miles between Bloomfield and village of Tariffville in the Town of Simsbury. The paved rail-trail passes through woods and fields with...
CT 1.8 mi Asphalt
The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
MA 3.6 mi Asphalt
The Columbia Greenway Rail Trail offers just over 3 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. About the Route The rail-trail runs between the Westfield...
MA 3.1 mi Asphalt
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
CT 49.1 mi Asphalt
Jonathan Daniels Trail travels the length of Ashuelot River Park through Keene. Along the stone-dust trail, you can enjoy the park’s beautiful natural backdrop and flower garden. The trail was named...
NH 0.9 mi Crushed Stone
The Keene Industrial Trail links the county's Cheshire Rail-Trail in the city of Keene. The paved path is a 1-mile segment through downtown Keene, which passes among some of the city's old mill...
NH 1 mi Asphalt
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
MA 9.5 mi Asphalt
The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail trail. The Mass Central Rail Trail runs for 64 miles between...
MA 64 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
The Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...
MA 5.7 mi Ballast, Cinder, Dirt, Grass
The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
MA 1.4 mi Asphalt
The South Spencer Rail Trail runs for less than 2 miles from downtown Spencer to an area south of town near Spencer State Forest. The path, which is also known as the Depot Trail, occupies a former...
MA 1.62 mi Crushed Stone
The Southwick Rail Trail extends for 6.5 miles between the Westfield town line south and the Massachusetts–Connecticut state line. About the Route Along the way, the Southwick Rail Trail travels...
MA 6.5 mi Asphalt
The Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
MA 0.7 mi Crushed Stone
Closure Notice: Due to flooding, the Ashuelot Recreational Rail Trail is closed from Pine Street to Sawyer's Crossing Road in Swanzey. Please see NH State Parks for more up-to-date information. The...
NH 21.4 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
The Common Pathway travels 5.5 miles from the outskirts of Peterborough south to downtown’s Noone Falls area, paralleling US 202 and the Contoocook River for most of its journey. The small town of...
NH 5.5 mi Asphalt, Crushed Stone
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
MA 7.8 mi Asphalt
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
NH 7 mi Ballast, Cinder, Dirt, Gravel, Sand
Harrisville and Hancock Rail Trails run for 6 miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris Center...
NH 6.1 mi Dirt
Accordion
The North Central Pathway is envisioned as a trail network connecting points of interest through and between Winchendon and Gardner. Several completed sections of trail make for a lovely ride or walk...
MA 11.2 mi Asphalt
The Old Railroad, as its name suggests, is a multi-use trail that occupies a former Boston & Maine Railroad corridor. The trail picks up at the northern trailhead of the Common Pathway, a paved...
NH 2.7 mi Dirt
Following the Nissitissit River through the woods, the Potanipo Rail Trail offers beautiful river views and launch sites for canoes or kayaks. Composed of two segments, the multi-use path is roughly...
NH 2.7 mi Crushed Stone, Gravel
The Rocky Hill Trail weaves through the tranquil greenery of the Burts Bog Greenway Conservation Area in Northampton, Hampshire County. The 121-acre peat bog is an ecologically sensitive site that's...
MA 0.9 mi Asphalt
The Squannacook River Rail Trail is 3.7 miles long, from Depot St in the center of Townsend, MA, to the Bertozzi Wildlife Management Area in Groton, MA. The trail occupies the Greenville Branch of the...
MA 3.7 mi Crushed Stone
The Toonerville Rail-Trail shadows the Black River for most of its 3.2-mile length in eastern Springfield to the border with New Hampshire across the Connecticut River. The route originally carried an...
VT 3.2 mi Asphalt
The Twin Cities Rail Trail is a 4-mile multi-use trail that connects downtown Fitchburg and downtown Leominster, offering a variety of recreational opportunities and providing an alternative...
MA 4 mi Asphalt
Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor...
CT 5.4 mi Asphalt
The Brookline Rail Trail winds through the New Hampshire woods and passes by several small bodies of water, including the Potanipo Pond. The rail-trail has two segments, known as the Brookline Rail...
NH 4.5 mi Crushed Stone, Gravel
The Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
MA 0.21 mi Asphalt
The Granite Town Rail-Trail runs for 3 miles in Milford, New Hampshire. Portions of the route are unpaved and surfaced with sand, gravel, and/or dirt, while short concrete sections can be found along...
NH 3 mi Ballast, Cinder, Dirt, Grass, Gravel, Sand
The scenic Valley Trail spans 9 miles connecting Dover and Wilmington in southern Vermont along the Green Mountain National Forest. It provides a critical off-road pathway for bypassing State Route...
VT 9.1 mi Asphalt, Dirt, Gravel
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection between Wheelock Park on the trail's west end and Ashuelot River...
NH 1.3 mi Asphalt
Running between downtown Bennington and the Northside Drive neighborhoods, the Bennington Rail Trail provides new opportunities for both recreation and active transportation. Following a former...
VT 1.65 mi Asphalt, Crushed Stone, Gravel

Recent Trail Reviews

Harrisville and Hancock Rail Trails

Not for everyone!

July, 2026 by ktrenaud

2.5 stars. Entered the trail a the far western end on Hancock Rd. near Skatutakee Lake. Biked eastward for several miles. Mixed surface (dirt, cinder, sand & forest floor). This trail is rough and best suited for fat-tire or full-suspension mountain bikes. You could do it with a gravel bike but be ready for a very bumpy ride. Partially buried track ties and roots cover roughly over a 3rd of this segment of the trail. The swamps and brook are absolutely beautiful. There are a few benches for a peaceful stop. The trail has a gentle decline most of the way so be prepared for the uphill on the return trip. Mostly shaded so sunscreen isn't needed but bug spray might be a good idea if stopping for prolonged periods. The bridges are beautiful & well maintained. The signage is discreet & informative. This is a wonderful all season trail that I plan to return to in foliage season. It has a lot of potential but in its current condition it has a LONG way to go to become a destination that will attract tourists & generate $$$ for the local economy.

Squannacook River Rail Trail

nice shorter ride

July, 2026 by slasalle76

Pleasant ride on this crushed stone surface, using my hybrid. Very short section that still has rails and ties and requests that bikes go around on the sidewalk, but easily joins back up to the actual trail after about 100 yards. The eastern end terminates in the Squannacook wildlife management area, with walking trails to follow down toward the river. If you are looking for a nice short ride that's under 10 miles total, this is a good one to choose. Stop for a bite at the local diner in Townsend center, or an ice cream.

Ashburnham Rail Trail

Short but scenic

June, 2026 by bhaalck

0.8 miles of this trail now consists of crushed gravel

Accordion

Hoosic River Greenway

Parked in middle waked each way, nice leisurely walk.

June, 2026 by tchioc88_tl

Parked in middle waked each way, nice leisurely walk.

Farmington Canal Heritage Trail

Rode Simsbury down to Plainville. Simsbury to Avon was full of tree root bumps, and lots of branches & trail debris. It's almost as if Simsbury wants to keep cyclists out. ¿ However, Avon and Farmington were great rides, as was Plainville.

June, 2026 by taccuosti

Rode Simsbury down to Plainville. Simsbury to Avon was full of tree root bumps, and lots of branches & trail debris. It's almost as if Simsbury wants to keep cyclists out. ¿ However, Avon and Farmington were great rides, as was Plainville.

South Spencer Rail Trail

Quite and Peaceful

May, 2026 by don.gerardi

Lot's of stops along the way to enjoy the sites. It's a very well maintained small trail

Ashuelot Recreational Rail Trail

pleasant ride

May, 2026 by slasalle76

I'd ridden this trail a couple years ago, doing it in small sections, and had found it to be a nice ride with a decent surface, quite reasonable for my older hybrid. I only did about 6 miles today, from Keene southward before turning back, and those couple of detours noted in another review are still in place - taking you out onto the road for short stretches likely to avoid power line work being done.

Farmington Canal Heritage Trail

Terrible Shape

May, 2026 by dave36

Rode from Avon, CT to Westfield, MA. Mass section in great shape. CT section is awful. Pavement is split, constant 'ka-thunk', pot holes not marked, just horrendous condition. Where is the CT DOT and our tax dollars? Stay away.

South Spencer Rail Trail

Quite and Peaceful

May, 2026 by don.gerardi

Lot's of stops along the way to enjoy the sites. It's a very well maintained small trail

Twin Cities Rail Trail

Nice enough.

May, 2026 by gbrosseau

Other reviews are fair. Lots of starts and stops for a shorter trail, but also some nice lengths and well maintained. Being from the area, I knew what to expect. I had more fun dodging and beeping my horn at bunnies on my night ride, than I did going around children on my day ride. Nice either way.

Valley Trail

Tough to do on a mountain bike, unless you're an expert. not maintained at all. I would say an ok hiking trail. But not all that scenic. Not what it's billed to be by a long shot.

May, 2026 by jim.thurber13

Tough to do on a mountain bike, unless you're an expert. not maintained at all. I would say an ok hiking trail. But not all that scenic. Not what it's billed to be by a long shot.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Varied Terrain, MultiUse, Lovely. Birds!

April, 2026 by susanadeleedwards

Went north out of Keene on the trail, and was quickly in a lovely wooded area, then soon at a side trail to Stonewall Farm, where visitors are welcome to wander. The birds were singing happily! We did 6.5 miles out before turning around but there was plenty more trail to explore. If you are expecting a super flat trail and a packed surface this may not be your kind of fun. If you don’t mind dismounting for a rickety bridge, or adventuring on side trails, then check this trail Out ,

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