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Greenfield, MA Dog Walking Trails and Maps

934 Reviews

Looking for the best Dog Walking trails around Greenfield?

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

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Activities
Length
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Type
50 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

Bridge of Flowers
0.1 mi
State: MA
Concrete

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

Grand Trunk Trail
6.9 mi
State: MA
Crushed Stone, Dirt, Gravel

Harrisville and Hancock Rail Trails
6.1 mi
State: NH
Dirt

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

Monadnock Recreational Rail Trail
7.5 mi
State: NH
Asphalt, 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

West River Trail (Windham County)
16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand

Westville Lake Community Trail
0.7 mi
State: MA
Crushed Stone
Accordion

Ashburnham Rail Trail
1.3 mi
State: MA
Dirt

Ashuelot Recreational Rail Trail
21.4 mi
State: NH
Asphalt, Ballast, Cinder, Crushed Stone, Dirt

Cheshire Rail Trail (Cheshire Branch Rail Trail)
42.4 mi
State: NH
Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

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

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

Old Railroad Trail
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

Windsor Locks Canal State Park Trail
5.4 mi
State: CT
Asphalt

Brookline Rail Trail
4.5 mi
State: NH
Crushed Stone, Gravel

Chicopee River Canal Rail Trail
0.21 mi
State: MA
Asphalt

Corkscrew Rail Trail
3.8 mi
State: NY
Dirt

Granite Town Rail-Trail
3 mi
State: NH
Ballast, Cinder, Dirt, Grass, Gravel, Sand

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
15 mi
State: MA
Ballast, Dirt, Grass, Gravel

Appel Way Trail
1.3 mi
State: NH
Asphalt

Valley Trail
9.1 mi
State: VT
Asphalt, Dirt, Gravel

Bennington Rail Trail
1.65 mi
State: VT
Asphalt, 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

Potanipo Rail Trail
3.4 mi
State: MA, NH
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 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
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
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 6.9 mi Crushed Stone, Dirt, Gravel
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
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 36.36 miles from...
 MA 56.36 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
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
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 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
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
Accordion
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
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 Cheshire Rail Trail connects Fitzwilliam, Troy, Keene, Westmoreland and Walpole. The 42.4-mile trail has a mostly gravel and dirt surface. The rail-trail plays host to a variety of uses,...
 NH 42.4 mi Asphalt, Ballast, Cinder, Dirt, Gravel, Sand
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
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
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
The Mason Railroad Trail runs for nearly 7 miles from near the New Hampshire–Massachusetts border (nr. Townsend, MA) to Greenville, NH. The trail follows a heavily wooded corridor through Russell...
 NH 6.7 mi Ballast, Gravel, Sand
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 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
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
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
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
The Ware River Rail-Trail is an unpaved 15-mile rail-trail that stretches between Barre and Baldwinville, running through Hubbardston and Templeton along the way.  Following along the Burnshirt...
 MA 15 mi Ballast, Dirt, Grass, 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
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
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
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
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
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

Recent Trail Reviews

Mass Central Rail Trail

A Delightful Ride on The Norwottuck Section

August, 2025 by gettinlate

June 6th 2025
The Mrs and I rode this beautiful trail from North Hampton to just short of Belchertown, and back.
The weather was great and the trail is mostly shaded, so the ride was superb.
I'd have no objection to doing it again.

read more …

Ashuwillticook Rail Trail

Settle grade difference between start to finish. All paved smooth.No bugs.Crowded with walkers, skaters, and bikers.Windy in the afternoon.

August, 2025 by joy.olson15

Settle grade difference between start to finish. All paved smooth.No bugs.Crowded with walkers, skaters, and bikers.Windy in the afternoon.

read more …

Ashuelot Recreational Rail Trail

Nice ride.

August, 2025 by cgtaylor328

We started at the south end and rode ten miles before turning around. We would have gone further except it was getting late. The trail over all is in good condition. There hasn’t been a lot of rainfall recently so the trail was dry. We ride ebikes with four inch off road tires. On the day we rode the condition of the trail was good enough for most riders but we don’t recommend road bikes.

read more …
Accordion

North Central Pathway

nice ride

August, 2025 by dmzast

rode trail july 28, 25 from Winchendon - slight uphill, going south to Gardner. Adding mile markers would be nice ! and directions at N.Ashburnham Rd to Old Gardner Rd. Newly paved from entrance off
Old Gardner Rd to Gardner town line. Path to avoid watery underpass was paved on one side of street.

read more …

Ashuwillticook Rail Trail

Update to my 2024 review

August, 2025 by andrix

Update to my 8/2024 review: Remains a TOP trail; At northern end easy parking at the Adams Visitor Center; Saw many signs of beaver activity - dams and huts - but no beavers. The Appalachian Trail crosses at Church Road in Cheshire; At southern end I turn back at the Crane Ave. parking area as, in my opinion, there's not much of interest in the remaining mile or so.

read more …

Blackstone River Greenway

one of my favorite trails

July, 2025 by wq6pp9sd4p

I live in Massachusetts about 25 minutes from this trail, my absolute favorite trail is the East Bay bike path, but that is about an hour drive for me, so this is one I frequent more often. I like the length of this ride, and that it is scenic, and more interesting than some of the rail trails that can be kind of boring. I think it is an easy ride, with just a few spots I need to lower my gears. I pack a lunch, snacks, and can be out for a few hours. There is ample parking, 195 Davison Ave Woonsocket is the address I use for WAZE. I have never gone as far as Providence, so I can only review Woonsocket - Lincoln.

read more …

Farmington Canal Heritage Trail

Needs Repaving

July, 2025 by dave36

Haven't ridden the trail since 2023. Rode from Cheshire down to New Haven, Saturday July 19th. Absolutely awful; entire section needs repaving and upkeep. Constant cracks in pavement and much debris on surface; plus glass and homeless down by the Wharf. Connecticut should take notice from Mass and NY on trail up keep. Both states's trail are far superior to CT. Also, difficult to navigate at trail end in New Haven if you don't know the city; poor signage.

read more …

Grand Trunk Trail

Pleasant Ride

July, 2025 by macmeier22

We are stayin at Pine Lake RV resort and wanted to do a paved bike ride. The gravel road reviews made me uncertain. But it was great. Some small inclines but nice ride to the Westville Dam. Very nice destination for a bike ride. Took road back on other side of dam. Much more mountain bike ride but still easy enough. So glad the parking lot was marked well. We almost drove 30 miles for another ride.

read more …

Ashuelot Recreational Rail Trail

I love this trail!

July, 2025 by 6z87r5x5ct

I have ridden this trail from one end to the other! Parts are wonderful and parts washed out and muddy!

read more …

Farmington Canal Heritage Trail

Quick notice: July 7 - 13: Section will be closed

July, 2025 by andrix

Beginning perhaps 2 miles north of the Simsbury Airport and continuing north for at least a few miles the trail will be closed for construction (looks like repaving + ?). I was on this trail yesterday and the "Will Be Closed" signs are abundant.

read more …

Ashuwillticook Rail Trail

Love the scenery. There are plenty of rest areas.

June, 2025 by sicnj2al

Love the scenery. There are plenty of rest areas.

read more …

Ashuwillticook Rail Trail

absolutely lovely

June, 2025 by sfrankovich

I rode this trail from the Northern tip south about 10 miles and back. It was very smooth pavement, a well marked trail and delightful views.

read more …
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Explore by Activity

ATV
Bike
Birding
Cross Country Skiing
Dog Walking
Fishing
Geocaching
Hiking
Horseback Riding
Inline Skating
Mountain Biking
Running
Snowmobiling
Walking
Wheelchair Accessible

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