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Greenfield, MA Hiking Trails and Maps

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Looking for the best Hiking trails around Greenfield?

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

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Name
Length
Most Popular

Ashuwillticook Rail Trail

13.7 mi

State: MA

Asphalt

Blackstone River Greenway

29.9 mi

State: MA, RI

Asphalt, Boardwalk, Crushed Stone, Dirt

Bloomfield Greenway Multi-Use Trail

1.8 mi

State: CT

Asphalt

Bridge of Flowers

0.1 mi

State: MA

Concrete

Canalside Rail Trail

3.6 mi

State: MA

Asphalt

Chicopee River Canal Rail Trail

0.21 mi

State: MA

Asphalt

Columbia Greenway Rail Trail

3.1 mi

State: MA

Asphalt

Farmington Canal Heritage Trail

47.6 mi

State: CT

Asphalt

Harrisville Rail Trail

1.6 mi

State: NH

Dirt

Jonathan Daniels Trail

0.9 mi

State: NH

Crushed Stone

Manhan Rail Trail

6 mi

State: MA

Asphalt

Mass Central Rail Trail

59 mi

State: MA

Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Monadnock Recreational Rail Trail

7.5 mi

State: NH

Asphalt, Gravel

Old Railroad Trail

2.7 mi

State: NH

Dirt

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

Twin Cities Rail Trail

4 mi

State: MA

Asphalt

West River Trail

16.1 mi

State: VT

Asphalt, Dirt, Gravel, Sand

Accordion

Westville Lake Community Trail

0.7 mi

State: MA

Crushed Stone

Ashuelot Recreational Rail Trail

21.5 mi

State: NH

Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Cheshire Rail Trail (Cheshire Branch Rail Trail)

32.9 mi

State: NH

Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Common Pathway

5.5 mi

State: NH

Asphalt, Crushed Stone

Connecticut Riverwalk and Bikeway

5.4 mi

State: MA

Asphalt

Fort Hill Recreational Rail Trail

7 mi

State: NH

Ballast, Cinder, Dirt, Gravel, Sand

Grand Trunk Trail

6.8 mi

State: MA

Crushed Stone, Dirt, Gravel

Granite Town Rail-Trail

3 mi

State: NH

Ballast, Cinder, Dirt, Grass, Gravel, Sand

Hoosic River Greenway

2.5 mi

State: NY

Gravel

Lye Brook Falls Trail

2.2 mi

State: VT

Gravel

Mason Railroad Trail

6.7 mi

State: NH

Ballast, Gravel, Sand

North Central Pathway

11.2 mi

State: MA

Asphalt

Potanipo Rail Trail (NH)

2.7 mi

State: NH

Crushed Stone, Gravel

Toonerville Rail-Trail

3.2 mi

State: VT

Asphalt

Windsor Locks Canal State Park Trail

5.4 mi

State: CT

Asphalt

Corkscrew Rail Trail

3.8 mi

State: NY

Dirt

Hillsborough Recreational Rail Trail

7.8 mi

State: NH

Crushed Stone, Dirt

Hoot, Toot and Whistle Trail & Riverwalk

2.3 mi

State: VT

Dirt

Ware River Rail-Trail

12 mi

State: MA

Ballast, Dirt, Grass, Gravel

Appel Way Trail

1.3 mi

State: NH

Asphalt

Ashburnham Rail Trail

1.3 mi

State: MA

Dirt

Valley Trail

9.1 mi

State: VT

Asphalt, Dirt, Gravel

Bennington Rail Trail

1.65 mi

State: VT

Asphalt, Crushed Stone, Gravel

Brookline Rail Trail

4.5 mi

State: NH

Crushed Stone, Gravel

Catamount Trail - Sections 1 and 2

18.1 mi

State: VT

Dirt

East Branch Trail (VT)

0.5 mi

State: VT

Gravel

Keene Industrial Heritage Trail

1 mi

State: NH

Asphalt

Potanipo Rail Trail

3.4 mi

State: MA, NH

Crushed Stone, Gravel

Rocky Hill Trail

0.9 mi

State: MA

Asphalt

Squannacook River Rail Trail

1.8 mi

State: MA

Crushed Stone

Trail Image	Trail Name	States	Length	Surface	Rating
	Ashuwillticook Rail Trail Overview 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...	MA	13.7 mi	Asphalt	100 reviews
	Blackstone River Greenway 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	29.9 mi	Asphalt, Boardwalk, Crushed Stone, Dirt	93 reviews
	Bloomfield Greenway Multi-Use Trail Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...	CT	1.8 mi	Asphalt	3 reviews
	Bridge of Flowers The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...	MA	0.1 mi	Concrete	4 reviews
	Canalside Rail Trail 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	13 reviews
	Chicopee River Canal Rail Trail 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	1 reviews
	Columbia Greenway Rail Trail Overview 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...	MA	3.1 mi	Asphalt	13 reviews
	Farmington Canal Heritage Trail Overview First a canal, then a railroad, and now a trail defines the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the...	CT	47.6 mi	Asphalt	155 reviews
	Harrisville Rail Trail The Harrisville Rail Trail runs for just under two miles between the outskirts of Harrisville and Hancock in rural New Hampshire. The former railroad bed is located on lands conserved by the Harris...	NH	1.6 mi	Dirt	1 reviews
	Jonathan Daniels Trail 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	1 reviews
	Manhan Rail Trail 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	6 mi	Asphalt	24 reviews
	Mass Central Rail Trail 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. Currently, nearly 60 miles from Boston to Northampton...	MA	59 mi	Asphalt, Cinder, Crushed Stone, Dirt, Gravel	90 reviews
	Monadnock Recreational Rail Trail The Monadnock Recreational Rail Trail is a great example of a repurposed rail route that provides safe commuting opportunities while also allowing trail users to escape into forest environments for...	NH	7.5 mi	Asphalt, Gravel	20 reviews
	Old Railroad Trail 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	1 reviews
	Quinebaug Valley Rail Trail 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	6 reviews
	Redstone Rail Trail 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	7 reviews
	South Spencer Rail Trail 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	3 reviews
	Southwick Rail Trail The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...	MA	6.5 mi	Asphalt	42 reviews
	Twin Cities Rail Trail The Twin Cities Rail Trail will be a 4.7-mile multiuse trail connecting downtown Fitchburg and downtown Leominster, providing a variety of recreational opportunities and an alternative transportation...	MA	4 mi	Asphalt	3 reviews
	West River Trail The West River Railroad, which once followed its namesake river for 36 miles, began passenger service in the late 1800s as a way to trim the two-day voyage between Brattleboro and South Londonderry to...	VT	16.1 mi	Asphalt, Dirt, Gravel, Sand	13 reviews

Accordion

Westville Lake Community Trail 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	1 reviews
Ashuelot Recreational Rail Trail 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	21.5 mi	Asphalt, Ballast, Cinder, Crushed Stone, Dirt	41 reviews
Cheshire Rail Trail (Cheshire Branch Rail Trail) Formerly comprising two separate segments—one running northward from Keene to Walpole, and the other running southward from Keene to Fitzwilliam—the Cheshire Rail Trail now runs a continuous 32.9...	NH	32.9 mi	Asphalt, Ballast, Cinder, Dirt, Gravel, Sand	45 reviews
Common Pathway 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	8 reviews
Connecticut Riverwalk and Bikeway 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	5.4 mi	Asphalt	16 reviews
Fort Hill Recreational Rail Trail 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	12 reviews
Grand Trunk Trail The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...	MA	6.8 mi	Crushed Stone, Dirt, Gravel	9 reviews
Granite Town Rail-Trail Overview 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...	NH	3 mi	Ballast, Cinder, Dirt, Grass, Gravel, Sand	3 reviews
Hoosic River Greenway The Hoosic River Greenway spans 2.5 miles along the river’s east bank through the Village of Hoosick Falls. The gravel pathway follows the former route of the Boston Hoosac Tunnel & Western Railway,...	NY	2.5 mi	Gravel	4 reviews
Lye Brook Falls Trail The heavily wooded Lye Brook Falls Trail runs for 2 miles through the Lye Brook Wilderness of the Green Mountain National Forest near Manchester. The blue-blazed hiking trail follows the bed of a...	VT	2.2 mi	Gravel	9 reviews
Mason Railroad Trail The Mason Railroad Trail runs for nearly 7 miles from near the New HampshireMassachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...	NH	6.7 mi	Ballast, Gravel, Sand	18 reviews
North Central Pathway 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	25 reviews
Potanipo Rail Trail (NH) 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	1 reviews
Toonerville Rail-Trail 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	7 reviews
Windsor Locks Canal State Park Trail 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	44 reviews
Corkscrew Rail Trail The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...	NY	3.8 mi	Dirt	5 reviews
Hillsborough Recreational Rail Trail Hillsborough Recreational Rail Trail connects three communities in south-central New Hampshire: Hillsborough, Deering, and Bennington. The unpaved trail winds along the Contoocook River through rural...	NH	7.8 mi	Crushed Stone, Dirt	11 reviews
Hoot, Toot and Whistle Trail & Riverwalk Although short, the Hoot, Toot and Whistle Trail provides an enjoyable journey through peaceful woodlands on Wilmington's west end. As you might guess, the rail-trail gets its name from the former...	VT	2.3 mi	Dirt	4 reviews
Ware River Rail-Trail This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...	MA	12 mi	Ballast, Dirt, Grass, Gravel	12 reviews
Appel Way Trail 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	1 reviews
Ashburnham Rail Trail More than a mile of the Ashburnham Rail Trail opened in 2015 from a point just south of Ashburnham's center to Turnpike Road. The rustic route, planned to be paved in the future, offers a...	MA	1.3 mi	Dirt	1 reviews
Valley Trail 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	5 reviews
Bennington Rail Trail 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	0 reviews
Brookline Rail Trail 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	0 reviews
Catamount Trail - Sections 1 and 2 The Catamount Trail offers 300 miles of backcountry skiing stretching across Vermont, from the Readsboro on the Massachusetts border, to North Troy near Canada. The trails are popular for winter...	VT	18.1 mi	Dirt	0 reviews
East Branch Trail (VT) The East Branch Trail is a 0.5-mile ungroomed, backcountry pathway built on a former logging railroad bed in southern Vermont's Windham County. The remote, heavily wooded trail lies just north of the...	VT	0.5 mi	Gravel	1 reviews
Keene Industrial Heritage Trail 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	0 reviews
Potanipo Rail Trail The Potanipo Rail Trail is composed of three segments across New Hampshire and Massachusetts. Running through the woods along a former a rail corridor, the trail parallels the Nissitissit River for a...	MA, NH	3.4 mi	Crushed Stone, Gravel	0 reviews
Rocky Hill Trail 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	0 reviews
Squannacook River Rail Trail The Squannacook River Rail Trail is presently 1.8 miles long, from Depot St. in the center of Townsend, MA, to the Harbor Church parking lot in Townsend Harbor. The trail occupies the Greenville...	MA	1.8 mi	Crushed Stone	0 reviews

Recent Trail Reviews

Blackstone River Greenway

We walked along the towpath section in Uxbridge and it was lovely. My daughter is in a wheelchair and it was doable, if not perfect. Park and enter from the Visitors' Center, and watch for the rocks and roots.

March, 2024 by wdncnu

We walked along the towpath section in Uxbridge and it was lovely. My daughter is in a wheelchair and it was doable, if not perfect. Park and enter from the Visitors' Center, and watch for the rocks and roots.

Canalside Rail Trail

You can expand your ride…..

March, 2024 by basil1986

I love this trail! Rode it on 3/14/24 when weather was 62 degrees. This trail is short but can be expanded if you cross the metal bridge by the brewery and take the road to the left leading to the Fish Research Hatchery on the opposite side of the canal. If you meander through the little neighborhood on that side as well you can extend it further and get another view of the old mill complexes. I get 20 miles out of the ride. Bring a lunch there are picnic tables on both sides!

Columbia Greenway Rail Trail

A gem of Westfield and the region

March, 2024 by jmchatton

The Columbia Greenway Rail Trail is a beautiful rail trail that has a little of everything. City views, farmland, rivers, and tree cover in just 3 miles. The bridges are also a feature that make this trail unique. I love that it connects to trails that go much further south into CT, so whether you are just going for a short walk or a long ride you can do it here! Plenty of access points too (including 4 in downtown Westfield alone) make it easy to get on the trail from nearby neighborhoods or get off to shop and eat at downtown businesses.

Accordion

Ashuwillticook Rail Trail

Not ADA compliant

February, 2024 by ljt trike rider

It looked very nice from the parking area, but could not get through the barricades with a recumbent trike. Drove over an hour and gates were shut and would have had to lift trike over gates. Disgusted with Massachusetts and whomever designed the barricades. Has anyone heard of the ADA?

Ashuwillticook Rail Trail

Great fall ride.

November, 2023 by cantabty

Excellent experience on this fresh paved trail. The scenery of the ponds and mountains in the distance was worth the trip.

Bloomfield Greenway Multi-Use Trail

Extension to Tariffville is complete

November, 2023 by bcgp

A sidepath has been constructed adjacent to Route 189 to Main St in Tariffville. Trail is now about 3 miles long. It will be designated as part of the East Coast Greenway and is visible on Google Street View.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

We found the Trail notTrail not as described

October, 2023 by luvaneezer

Cheshire Trail South. Rode north from State Line Circle toward Kenne. We are experienced road cyclists, now riding gravel bikes. We are looking for reasonably surfaced longer trails and hoped this would be one of them. Sadly, we found this trail to be rocky, rutted, with lots of roots, and uncleared blowdown. The vigilance required to remain upright made it difficult to enjoy the beauty all around. The suddenly occurring steep inclines to roads seemed borderline dangerous. If we lived closer it would be a great trail to walk with the dogs

Ashuelot Recreational Rail Trail

Still a lovely ride in spite of washouts

September, 2023 by nanlovell77

I would hate for people to avoid this lovely trail because of reports of the washouts. By using the trail map from this app or even Google maps you can easily find nearby roads that allow you to ride around the closed sections. We had a lovely 18.7 mi ride today and we’re able to keep cool because of lots of shade even though it got up to 90 degrees! They were repairing the bridge on the road to the Slate Covered Bridge, but they paused work to let us cross. It will be repaired very soon.

Monadnock Recreational Rail Trail

Pleasantly Surprised

September, 2023 by fyredown

Truly a nice ride this weekend. Packed surface, mixed terrain but nothing our Surly Ogre's couldn't handle. This was not a crowded trail but there were a spattering of walkers, bikers, dog walkers. Made you feel happy to be alive! Whoever is maintaining this trail - thank you!

Hillsborough Recreational Rail Trail

Bennington to Deering - compared with Jaffrey to Rindge

September, 2023 by fyredown

What will it take to get the Bennington to Deering Rail Trail suitable for bicycle??? It is a very difficult ride with even fat-tired riders because of the loose terrain. And then if you try to avoid it by riding the road, that is almost impossible also due to all the pitfalls and holes. This could be such an attraction.

I tried the Jaffrey to Rindge trail this weekend and there was NO COMPARISON! Fun, enjoyable ride while this one remains disappointing.

Please put this one on your list to help!!!

Ashuwillticook Rail Trail

Good scenic ride

September, 2023 by richmedcraft

I rode the trail from Pittsfield to the end in North Adams and back on 8/5/23. The trail is paved and in good condition and restrooms at the Pittsfield trail head were clean and working fine. Nice scenery including lakes and the Berkshires- I was able to finally identify Mt Greylock after the morning clouds had dissipated. The grade is gentle and I was able to keep up a consistent pace for the ride.

Monadnock Recreational Rail Trail

not great conditions

September, 2023 by emilyahagan

A mix of sand, packed gravel and flooded trail. Rather challenging terrain that required skilled navigating the trail . It was in horrible condition. The brewery in winchendon was wonderful, but you need to bushwhack through the trail and into an abandoned factory’s parking lot.

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