Greenfield, MA Dog Walking Trails and Maps

790 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
Surfaces
Type
45 Results
Activities
Length
Surfaces
Type

Appel Way Trail

1.3 mi
State: NH
Asphalt

Ashburnham Rail Trail

1.3 mi
State: MA
Dirt

Ashuelot Recreational Rail Trail

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

Ashuwillticook Rail Trail

11.9 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

Cheshire Rail Trail (Cheshire Branch Rail Trail)

32.9 mi
State: NH
Asphalt, Ballast, Cinder, Dirt, Gravel, Sand

Chicopee River Canal Rail Trail

0.21 mi
State: MA
Asphalt

Columbia Greenway Rail Trail

2.4 mi
State: MA
Asphalt

Common Pathway

5.5 mi
State: NH
Asphalt, Crushed Stone

Connecticut Riverwalk and Bikeway

5.4 mi
State: MA
Asphalt

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

East Branch Trail (VT)

0.5 mi
State: VT
Gravel

Farmington Canal Heritage Trail

48.3 mi
State: CT
Asphalt

Fort Hill Recreational Rail Trail

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

Grand Trunk Trail

6.2 mi
State: MA
Crushed Stone, Dirt, Gravel

Granite Town Rail-Trail

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

Harrisville Rail Trail

1.6 mi
State: NH
Dirt

Hillsborough Recreational Rail Trail

7.8 mi
State: NH
Crushed Stone, Dirt

Hoosic River Greenway

2.5 mi
State: NY
Gravel

Hoot, Toot and Whistle Trail

0.5 mi
State: VT
Dirt

Jonathan Daniels Trail

0.9 mi
State: NH
Crushed Stone

Keene Industrial Heritage Trail

1 mi
State: NH
Asphalt

Lye Brook Falls Trail

2.2 mi
State: VT
Gravel

Manhan Rail Trail

9.6 mi
State: MA
Asphalt

Mason Railroad Trail

6.7 mi
State: NH
Ballast, Gravel, Sand

Mass Central Rail Trail

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

Monadnock Recreational Rail Trail

7.5 mi
State: NH
Asphalt, Gravel

North Central Pathway

8.9 mi
State: MA
Asphalt

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

Rocky Hill Trail

0.9 mi
State: MA
Asphalt

South Spencer Rail Trail

1.62 mi
State: MA
Crushed Stone

Southwick Rail Trail

6.5 mi
State: MA
Asphalt

Squannacook River Rail Trail

1.8 mi
State: MA
Crushed Stone

Toonerville Rail-Trail

3.2 mi
State: VT
Asphalt

Valley Trail

9.1 mi
State: VT
Asphalt, Dirt, Gravel

Ware River Rail-Trail

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

West River Trail

16.1 mi
State: VT
Asphalt, Dirt, Gravel, Sand

Westville Lake Community Trail

0.7 mi
State: MA
Crushed Stone
Trail Image Trail Name States Length Surface Rating
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
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
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
NH 21.5 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along this nearly 12-mile-long paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through...
MA 11.9 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 29.9 mi Asphalt, Boardwalk, Crushed Stone, Dirt
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
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 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
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
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 Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River Bridge...
MA 2.4 mi Asphalt
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 5.4 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 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
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 48.3 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 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 6.2 mi Crushed Stone, Dirt, Gravel
Mile 0.0 - DPW Garage  Cross the bridge in the parking area, the trail starts behind the fence, crossing over Great Brook on a old dam. Mile 0.53 - After crossing Union St. you will come to a...
NH 3 mi Ballast, Cinder, Dirt, Grass, Gravel, Sand
Accordion
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
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
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
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 0.5 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 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 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 9.6 mi Asphalt
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 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 50 miles from Boston to Northampton...
MA 48.4 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 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 8.9 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
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 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 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 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
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
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 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
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
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
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

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Trails by activity

Recent Trail Reviews

Windsor Locks Canal State Park Trail

A beautiful trail in need of resurfacing

May, 2022 by eajack

My wife and I rode our recumbent trikes on the entirety of this trail on a Saturday evening. For the most part, we encountered only walkers. And based on the surface condition of the trail, I understand why. The pavement has deteriorated and is full of root-bumps and small dips. It was a very rough ride.

I would recommend this trail for walkers, joggers, or cyclists if you've got a bike/trike with a suspension. The bulk of the trail is on the old towpath between the river and the canal, so other than the north and south ends, you are separated by water from the rest of the world. This makes for a quiet, relaxing, and scenic trek. The northern terminus near the parking lot, which also forms a "T" with the CT 190 bridge, and the southern terminus by the renovated mill building are new and in great shape. All we need now is for Connecticut to resurface the original portion... even stone dust would be better than the broken pavement.

Ashuwillticook Rail Trail

Ashuwillticook Rail Trail

May, 2022 by bktourer1

If you haven't seen or been there yet, new 1.5 section towards Pittsfield was officially opened last week. Ends/Starts at Crane Road. Parking lot and toilets are available. New dirt lot on Rt. 8 before you turn off US7/Rt 8 connector road

Blackstone River Greenway

Woonsocket to Cumberland

May, 2022 by andrix

Beautiful day on this section of the Blackstone River Greenway. Trail is paved entire way and in very good shape with only a handful of road crossings. There were relatively few walkers/riders (Thursday), some benches along the way, a number of signs with historical write-up and nice views of some waterfalls. Overall an excellent 20 RT ride. Gave it a 4 only because of a few long "average views" stretches. The 195 Davidson Ave, Woonsocket, RI (northern point) address for GPS worked great.

Accordion

North Central Pathway

connecting on

May, 2022 by mdenettesr

We continued on to the MA/NH line and connected to Cheshire Trail to Keene, switched to Ashuelot and connected to The Fort Hill in Hinsdale, NH. Gardner to Brattleboro via Keene! All good trails.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Encountered a closure north from Hurricane Rd. Not sure how far, but sign says until the end of June. Unfortunately my favorite section!

April, 2022 by leamble

Encountered a closure north from Hurricane Rd. Not sure how far, but sign says until the end of June. Unfortunately my favorite section!

Farmington Canal Heritage Trail

Farmington to Canton

April, 2022 by aldcon_tl

Great trail and very scenic. All paved and pavement in very good shape. Parked at lot on New Britain Ave. and went NW to Collinsville and then to Rte. 44 in Canton. Then rode trail back to start.
10 miles each way. Very enjoyable journey. 90%+ of ride is on nice wide trail. First half of trip is constant, gentle up gradient. Ride back about 60% faster since going mostly gently downhill along river.

Connecticut Riverwalk and Bikeway

Awesome run, it was late 40th and windy however i was so happy to run outside. I like the river view and and it's away from the traffic. I can get a decent 6 miles out it. Good place to stretch by the stairs amazing view.

February, 2022 by yikertam

Awesome run, it was late 40th and windy however i was so happy to run outside. I like the river view and and it's away from the traffic. I can get a decent 6 miles out it. Good place to stretch by the stairs amazing view.

Fort Hill Recreational Rail Trail

Trail maintenance

February, 2022 by buck1786.wr

This trail is maintained my The Pisgah Mtn. Trailriders club which is a local snowmobile club here in Hinsdale. We as a club try our best to keep this trail open for all of it's intended purposes by keeping the trail clear of downed trees cutting the grass and grooming the trails for snowmobiling. The only help we get from the State of N.H. is some grant money for grooming the trails in the wintertime. All other expenses come out of our pocketbook. Hopefully in the future this trail will get a total facelift and be in tip top shape but in the mean time we're doing the best we can. Remember we're all volunteers and always looking for new members. Thanks

Windsor Locks Canal State Park Trail

wow ¿

November, 2021 by pnd5qqtvsk

What a cool, beautiful, pleasant surprise. So glad I decided to check this trail out. Nice parking lot adjacent to the mill apartments on southern end. Road the entire thing including the T portion across the river to Enfield and to the west into Suffield. I will go again and bring some friends. So picturesque.

West River Trail

Jamaica base trail

October, 2021 by drkateklemer

the first 2 miles were gorgeous and great rail trail packed gravel. After that we stopped at the base of a narrow rocky hill. The Brattleboro portion was great, 4 miles each way. I may go north sometime and try the top on down. I have an e bike with no shock forks/ trek verve 3. So not a mountain bike per se…

Ashuelot Recreational Rail Trail

nice ride

October, 2021 by drkateklemer

I preferred from Hillsdale. It is a bit bumpy at first. Rides on a ridge and along a river. We rode about 9 miles in from Hillsdale. Really enjoyed it! Interesting decrepid factory buildings along the river and a beautiful bridge. I have a trek verve 3 pedal assist without any special tires or front fork shock absorbers. It was mostly fine, a big puddle finally got us to turn around.

Grand Trunk Trail

I drove to find this trail two times and could not find where it begins or where to park. I'm glad for those who love it, but in using both the map and GPS, I can not find it??

October, 2021 by davehmv

I drove to find this trail two times and could not find where it begins or where to park. I'm glad for those who love it, but in using both the map and GPS, I can not find it??

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