Westfield, MA Dog Walking Trails and Maps

1359 Reviews

Looking for the best Dog Walking trails around Westfield?

Find the top rated dog walking trails in Westfield, 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
53 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

60.3 mi
State: CT
Ballast, Crushed Stone, Dirt, Gravel

Ashuwillticook Rail Trail

13.7 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

Cheney Rail Trail

1.7 mi
State: CT
Crushed Stone

Columbia Greenway Rail Trail

3.1 mi
State: MA
Asphalt

Farmington Canal Heritage Trail

48.9 mi
State: CT
Asphalt

Farmington River Trail

16.5 mi
State: CT
Asphalt, Concrete, Crushed Stone

Hanover Pond Trail

1 mi
State: CT
Asphalt

Harlem Valley Rail Trail

26.2 mi
State: NY
Asphalt

Hartford Riverwalk

1.7 mi
State: CT
Asphalt

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Kress Family Trail

3.1 mi
State: CT
Dirt

Litchfield Community Greenway

2.5 mi
State: CT
Boardwalk, Crushed Stone, Dirt

Manhan Rail Trail

9.5 mi
State: MA
Asphalt

Mass Central Rail Trail

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

Quinebaug River Trail

4.8 mi
State: CT
Asphalt

Quinebaug Valley Rail Trail

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

Quinnipiac River Gorge Trail

1.3 mi
State: CT
Asphalt

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

Sue Grossman Still River Greenway

3.4 mi
State: CT
Asphalt

Westville Lake Community Trail

0.7 mi
State: MA
Crushed Stone

Windsor River Trail

0.8 mi
State: CT
Asphalt

Ashuelot Recreational Rail Trail

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

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Captain John Bissell Trail

4.5 mi
State: CT
Asphalt

Charter Oak Greenway

16.5 mi
State: CT
Asphalt

Connecticut Riverwalk and Bikeway

7.8 mi
State: MA
Asphalt

Fort Hill Recreational Rail Trail

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

Grand Trunk Trail

6.9 mi
State: MA
Crushed Stone, Dirt, Gravel

Larkin State Park Trail

10.8 mi
State: CT
Cinder, Crushed Stone, Dirt, Gravel

Mattabassett Trolley Trail

2.9 mi
State: CT
Asphalt

Middlebury Greenway

4.5 mi
State: CT
Asphalt

North Central Pathway

11.2 mi
State: MA
Asphalt

Putnam River Trail

2 mi
State: CT
Asphalt

Quinnipiac Linear Trail

2.1 mi
State: CT
Asphalt, Gravel

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

Rocky Hill Trail

0.9 mi
State: MA
Asphalt

Southern New England Trunkline Trail

21.8 mi
State: MA
Asphalt, Ballast, Crushed Stone

Chicopee River Canal Rail Trail

0.21 mi
State: MA
Asphalt

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Ware River Rail-Trail

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

Billings Trail

3.3 mi
State: CT
Dirt

Naugatuck River Greenway

7.4 mi
State: CT
Asphalt

Middletown Westlake Area Bikeway

2.2 mi
State: CT
Asphalt
Trail Image Trail Name States Length Surface Rating
Overview The Air Line State Park Trail winds 60.3 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway...
CT 60.3 mi Ballast, Crushed Stone, Dirt, Gravel
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
Overview 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...
MA, RI 31.6 mi Asphalt, Boardwalk, Crushed Stone, Dirt
Overview 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...
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
Overview The Cheney Rail Trail is a 1.7-mile trail with a crushed stone surface in downtown Manchester. About the Route The trail is mostly shaded and a pleasant walk any time of the year....
CT 1.7 mi Crushed Stone
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
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 48.9 mi Asphalt
Overview A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The...
CT 16.5 mi Asphalt, Concrete, Crushed Stone
The Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...
CT 1 mi Asphalt
Overview Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful 26.2-mile wooded pathway along the former New York &...
NY 26.2 mi Asphalt
The Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...
CT 1.7 mi Asphalt
Overview It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail trail dive through steep...
CT 20 mi Crushed Stone
The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
CT 3.1 mi Dirt
The Litchfield Community Greenway runs along the former Shepaug Railway railbed in the Town of Litchfield. Operational from 1878 to 1948, the railroad line ran between between Litchfield and...
CT 2.5 mi Boardwalk, Crushed Stone, Dirt
Overview 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,...
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. Currently, nearly 60 miles from Boston to Northampton...
MA 59 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
The Quinebaug River Trail exists in two segments in northwest Connecticut. The northern section parallels Park Road and Tracy Road for about 2 miles in an industrial section of Putnam with few trail...
CT 4.8 mi Asphalt
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
Accordion
The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
CT 1.3 mi Asphalt
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
Overview 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...
MA 6.5 mi Asphalt
Just over 3 miles long, the Sue Grossman Still River Greenway is anchored by Winsted to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck Division of the New York,...
CT 3.4 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
The Windsor River Trail is a paved trail along the Connecticut River in Windsor Meadows State Park. The trail begins at the state park’s parking lot on E Barber St. The Captain John Bissell Trail,...
CT 0.8 mi Asphalt
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...
NH 21.4 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt
A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...
CT 4.4 mi Asphalt, Concrete
The Bissell name looms large in this part of New England, and has been immortalized in multiple ways, including the Bissell Ferry, the Bissell Memorial Bridge and now, the Captain John Bissell trail,...
CT 4.5 mi Asphalt
Overview The Charter Oak Greenway offers more than 16 miles of paved pathways through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but...
CT 16.5 mi Asphalt
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 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
Overview The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. About the Route Horseback riders use this trail...
CT 10.8 mi Cinder, Crushed Stone, Dirt, Gravel
Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...
CT 2.9 mi Asphalt
The Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an amusement...
CT 4.5 mi Asphalt
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 Putnam River Trail extends between Arch Street in the Putnam District and Providence Street to the south. The trail follows the east bank of the Quinebaug River between the river and Kennedy...
CT 2 mi Asphalt
The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
CT 2.1 mi Asphalt, Gravel
The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
CT 1.7 mi Asphalt, Dirt, Grass
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
Overview The Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven...
MA 21.8 mi Asphalt, Ballast, Crushed Stone
The Rockville Spur, a section of Vernon Rails-to-Trails, is a stone-dust rail-trail stretching 4.1 miles into the heart of historical Rockville. The trail begins on Warren Avenue in Vernon, but you’ll...
CT 4.1 mi Crushed Stone, Dirt
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 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 Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. The...
CT 1.2 mi Asphalt, Cinder, Crushed Stone
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
Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...
CT 3.3 mi Dirt
The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short, disconnected segments totaling just over 7 miles. The...
CT 7.4 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
Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...
CT 2.2 mi Asphalt

Recent Trail Reviews

Blackstone River Greenway

Wonderful trail

November, 2024 by walkinator007

This is my favorite trail in the state, very scenic along the river. best part is from woonsocket to lincoln. Some parts of this trail through the city are poorly marked and you need to share the road with cars.

Harlem Valley Rail Trail

Everything you could ask for

October, 2024 by robert.richter89

I rode the entire 24.7 mile southern portion of the Harlem Valley Rail Trail on a beautiful fall day. The HVRT offers everything you could want from a trail experience: a fully paved surface, mostly flat, beautiful scenery (especially in the Fall) and a perfect mid-point trailhead to grab a bite to eat.

I don't recall seeing any water fountains along the trail although the trailhead in Millerton offers many options for places to eat or resupply. The HVRT offers a myriad of scenery changes from farmland, quiet streams, distant hills to quaint towns. I have ridden many paved rail trails in the past and the HVRT is one of the best with almost no surface imperfections for the entire distance. There are many trailheads along the entire trail giving many distance options. All this adds up to a perfect trail in my opinion!

Harlem Valley Rail Trail

trail is complete now but map not updated

October, 2024 by vbergerg_tl

Map is 6 months out of date

Accordion

Ashuwillticook Rail Trail

Mid-Fall Ride

October, 2024 by willipar

Rode the full trail on a glorious October Saturday. the views were spectacular, peppered with fiery fall leaves. The trail is in incredibly good condition over the whole length. Such a lovely ride.

Canalside Rail Trail

Trail Closed

October, 2024 by joerone_tl

Part of this trail is closed, my wife and I got about 2 miles or so in and there was a detour sign for the trail and we could not find where it picked up again. Road on the streets for a bit and then headed back to the truck, got about 5 miles in on the ride so not a total loss

Fort Hill Recreational Rail Trail

great trail

September, 2024 by leslie.sherman316

We did this trail today. It is quite bumpy but the scenery more than makes up for that. It goes through beautiful forests with frequent views of the Connecticut River. Don’t pass it up if you are in the area.

Cheney Rail Trail

Cheney Trail

September, 2024 by nicoleh742

Hubby and I discovered this trail last fall. We absolutely love it. It's a beautiful hike with all the leaves changing. Great for pets too as it's a pretty flat walk. It's def longer than 1.7 miles though. I love that the leaves are changing we will be frequented this trail alot during this fall season!

Cheney Rail Trail

Cheney Trail

September, 2024 by nicoleh742

Hubby and I discovered this trail last fall. We absolutely love it. It's a beautiful hike with all the leaves changing. Great for pets too as it's a pretty flat walk. It's def longer than 1.7 miles though. I love that the leaves are changing we will be frequented this trail alot during this fall season!

Air Line State Park Trail

We had a great ride! 6.6 miles. Beautiful day!

September, 2024 by susanmazur13

We had a great ride! 6.6 miles. Beautiful day!

Mass Central Rail Trail

Weston-Waltham section

September, 2024 by msandman1943_tl

This section (8/2024) is about 5 miles long. It goes through woodland and past leafy backyards, but it runs alongside the towers for a high-tension power line. Trees have been clear-cut about 25 feet on both sides of the trail, so there's no shade along this section. But the trail is wide, very straight, and smoothly paved. It has a few small ups and downs and crosses four or five quiet roads before it comes to a traffic signal at the intersection of Routes 126 and 27. Just beyond, the trail turns to crushed stone with a few sandy patches. There's a large supermarket and shopping center adjacent to the trail at that point.

Southwick Rail Trail

Very busy on sunny weekend, well kept trail

September, 2024 by mdnkcn

We started going north on Copper Hill Rd East Granby Ct parking area and finished the trail in Westfield MA. Trail was all asphalt and in good shape. Most of the trail was scenic farmland but toward the north end going toward Westfield was some residential and city though still was plesent to the eye. Next time we plan to take the trail south at the Copper Hill Parking and take the trail to where it hopefully meets the Farmington River Trail

Blackstone River Greenway

Mile 17-7 going south from Woonsocket the trail is marked. Very enjoyable ride.

September, 2024 by buckley02

Mile 17-7 going south from Woonsocket the trail is marked. Very enjoyable ride.

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