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Litchfield, CT Dog Walking Trails and Maps

1647 Reviews

Looking for the best Dog Walking trails around Litchfield?

Find the top rated dog walking trails in Litchfield, 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
66 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail
60.3 mi
State: CT
Ballast, Crushed Stone, Dirt, Gravel

Albany-Hudson Electric Trail
26.6 mi
State: NY
Asphalt, Crushed Stone

Ashokan Rail Trail
11.5 mi
State: NY
Crushed Stone

Ashuwillticook Rail Trail
13.7 mi
State: MA
Asphalt

Bloomfield Greenway Multi-Use Trail
1.8 mi
State: CT
Asphalt

Branford Trolley Trail
0.6 mi
State: CT
Concrete, Crushed Stone, Gravel

Columbia Greenway Rail Trail
3.1 mi
State: MA
Asphalt

Farmington Canal Heritage Trail
47.6 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

Hudson Valley Rail Trail
7.1 mi
State: NY
Asphalt

Kennedy Trail
1.7 mi
State: NY
Cinder

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

Maybrook Trailway
28.6 mi
State: NY
Asphalt
Accordion

North County Trailway
20.7 mi
State: NY
Asphalt

Pequonnock River Trail
14.5 mi
State: CT
Asphalt, Crushed Stone

Putnam Trailway
11.8 mi
State: NY
Asphalt

Quinnipiac River Gorge Trail
1.3 mi
State: CT
Asphalt

Redstone Rail Trail
1.4 mi
State: MA
Asphalt

River-to-Ridge Trail
4.9 mi
State: NY
Gravel

Southwick Rail Trail
6.5 mi
State: MA
Asphalt

Sue Grossman Still River Greenway
3.4 mi
State: CT
Asphalt

Walkway Over The Hudson
1.6 mi
State: NY
Concrete

Wallkill Valley Rail Trail
21.4 mi
State: NY
Asphalt, Cinder, Dirt, Gravel

William R. Steinhaus Dutchess Rail Trail
13.8 mi
State: NY
Asphalt

Windsor River Trail

0.8 mi
State: CT
Asphalt

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

Cheney Rail Trail
1.7 mi
State: CT
Crushed Stone

Connecticut Riverwalk and Bikeway
5.4 mi
State: MA
Asphalt

Kingston Point Rail Trail
2.15 mi
State: NY
Asphalt

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

New Milford River Trail
5 mi
State: CT
Asphalt, Crushed Stone, Dirt

O&W Rail Trail (Ulster County)
18 mi
State: NY
Asphalt, Cinder, Crushed Stone, Dirt, Grass

Old Croton Aqueduct Trail
26.5 mi
State: NY
Crushed Stone, Dirt, Grass, Gravel

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

Savin Rock Trail
1.2 mi
State: CT
Asphalt, Concrete

Shoreline Greenway Trail
4.1 mi
State: CT
Crushed Stone, Dirt

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)
4.1 mi
State: CT
Crushed Stone, Dirt

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

Briarcliff-Peekskill Trailway
12 mi
State: NY
Asphalt, Dirt, Grass

Chicopee River Canal Rail Trail
0.21 mi
State: MA
Asphalt

Derby Greenway
1.97 mi
State: CT
Asphalt, Dirt

Norwalk River Valley Trail
12.2 mi
State: CT
Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel

Ridgefield Rail Trail
2.3 mi
State: CT
Gravel

Stratton Brook State Park Trail
1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Old Mine Railroad Trail
2.2 mi
State: NY
Dirt

Billings Trail
3.3 mi
State: CT
Dirt

Naugatuck River Greenway
7.4 mi
State: CT
Asphalt

Hudson River Brickyard Trail
1.5 mi
State: NY
Asphalt, Woodchips

Klara Sauer Trail
1 mi
State: NY
Crushed Stone

Marcus J. Molinaro Northside Line
0.57 mi
State: NY
Asphalt

Middletown Westlake Area Bikeway

2.2 mi
State: CT
Asphalt

Midtown Linear Park
0.9 mi
State: NY
Asphalt

Mohansic Trailway
1 mi
State: NY
Boardwalk, Dirt, Gravel
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 The Albany-Hudson Electric Trail (AHET) follows a 36-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. There are several...
 NY 26.6 mi Asphalt, Crushed Stone
Overview The Ashokan Rail Trail is an 11.5-mile multi-use trail that traces the northern edge of the Ashokan Reservoir, which provides a large proportion of New York City's drinking water. The...
 NY 11.5 mi Crushed Stone
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 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
Overview The Branford Trolley Trail is essentially a 0.6-mile footbridge occupying an old bridge along the route of an abandoned trolley track. About the Route The long bridge links nature...
 CT 0.6 mi Concrete, Crushed Stone, Gravel
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 47.6 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
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 rock cuts...
 CT 20 mi Crushed Stone
Overview Offering a picturesque and family-friendly adventure, the Hudson Valley Rail Trail stretches 7.1 miles through hardwood forests, over Black Creek, and under two spectacular stone-arch...
 NY 7.1 mi Asphalt
The Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers.  The cinder trail, built on a former rail bed,...
 NY 1.7 mi Cinder
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
Closure Notice: Due to flooding and storm damage, the Maybrook Trailway from Green Haven Rd. to Depot Hill Rd. See Empire State Trail for more current information. Overview The Maybrook Trailway...
 NY 28.6 mi Asphalt
Accordion
Overview At just over 20 miles, the North County Trailway is the longest of four rail trails created from the former New York Central Railroad’s Putnam Division line. The trail travels through...
 NY 20.7 mi Asphalt
Note: ALL Trumbull town parks require permit parking stickers year-round (also noted on the signboards at each park entrance).  Overview  The Pequonnock River Trail is the formal name for this...
 CT 14.5 mi Asphalt, Crushed Stone
Overview  The old New York Central rail line that ran from the Bronx to communities north of the city in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends,...
 NY 11.8 mi Asphalt
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
Connecting the Walkill River and Shawangunk Ridge, the aptly named River-to-Ridge Trail, which opened in September 2018, runs from New Paltz to the Mohonk Preserve. Begin at the Carmine Liberta Bridge...
 NY 4.9 mi Gravel
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
Overview The Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at 1.28 miles—emerges from the trees and over the rooftops of the old riverfront town of...
 NY 1.6 mi Concrete
Overview The Wallkill Valley Rail Trail runs 21.4 miles between Kingston and Gardiner through woods, fields, farmland. About the Route The corridor’s current incarnation as a linear park...
 NY 21.4 mi Asphalt, Cinder, Dirt, Gravel
Overview The William R. Steinhaus Dutchess Rail Trail—named for the Dutchess County executive who championed it—is a treasure in New York's Hudson Valley region. The 13.8-mile trail runs through...
 NY 13.8 mi Asphalt
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
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
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
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
Overview The Kingston Point Rail Trail is a paved pathway stretching from Kingston’s midtown to the Rondout Creek waterfront, connecting important points in the community such as Kingston High...
 NY 2.15 mi Asphalt
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 first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
 CT 5 mi Asphalt, Crushed Stone, Dirt
Overview The O&W Rail Trail follows the route of the old NY O&W Railroad (Kingston-Port Jervis Branch) right-of-way for 19.1 miles through Ulster County, NY, between Kingston and Ellenville. The...
 NY 18 mi Asphalt, Cinder, Crushed Stone, Dirt, Grass
Overview The Old Croton Aqueduct Trail spans 26.5 miles across West Chester County, NY. It is often a singletrack dirt pathway that winds through communities and trees and provides an oasis of...
 NY 26.5 mi Crushed Stone, Dirt, Grass, Gravel
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
The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...
 CT 1.2 mi Asphalt, Concrete
When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...
 CT 4.1 mi Crushed Stone, Dirt
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 Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...
 NY 12 mi Asphalt, Dirt, Grass
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
Overview Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made...
 CT 1.97 mi Asphalt, Dirt
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
 CT 12.2 mi Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel
The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...
 CT 2.3 mi Gravel
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
Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...
 NY 2.2 mi Dirt
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 Hudson River Brickyard Trail runs 1.5 miles from North Street to John Street in East Kingston. Located in Sojourner Truth State Park, the trail follows the shoreline and offers scenic views of...
 NY 1.5 mi Asphalt, Woodchips
The Klara Sauer Trail (formerly known as the Beacon Riverside Trail) runs for 1 mile along the Hudson River on the west side of New York's village of Beacon. The trail occupies the same corridor as...
 NY 1 mi Crushed Stone
The Marcus J. Molinaro Northside Line is a 0.57 mile dual-track trail that connects trail users between the city and town of Poughkeepsie. While the northern end of the route is still under...
 NY 0.57 mi Asphalt
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
Following the former Ulster & Delaware Railroad (U&D) corridor, the Midtown Linear Park is part of the Kingston Greenline. Running through Midtown between Westbrook Lane and Cornell Street, the ADA...
 NY 0.9 mi Asphalt
The Mohansic Trailway is a rail-trail providing an important link between the North County Trailway and the Franklin Delano Roosevelt State Park. The trailway occupies a short-lived spur of the New...
 NY 1 mi Boardwalk, Dirt, Gravel

Recent Trail Reviews

William R. Steinhaus Dutchess Rail Trail

Hopewell Junction

September, 2024 by flywithme_tl

Went from the Thuway area in Poughkeepsie over the walkway and ride to Hopewell junction .Nice trail well groomed , paved not much to look at but very cool what the volunteers did to the RR depot , signal house and pavilion, the depot museum was great . Went to Daddy O’s restaurant on the trail , good food . The NY empire trail continues along live tracks goes I believe quite far .

read more …

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!

read more …

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.

read more …
Accordion

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

read more …

O&W Rail Trail (Ulster County)

O&W Kingston

September, 2024 by flywithme_tl

Nice trail a must do . From Kingston it’s paved at least 5 -6 miles the rest is easy ride great scenery !

read more …

Chicopee River Canal Rail Trail

Unfinished trail. Did not feel safe on portions of the trail.

August, 2024 by bdrzyzga

Unfinished trail. Did not feel safe on portions of the trail.

read more …

Ashuwillticook Rail Trail

Late summer ride

August, 2024 by mgraska54

Beautiful smooth ride. Recommend for anyone seeking a pleasurable experience.

read more …

Maybrook Trailway

weeds weeds weeds!!!

August, 2024 by johnjr4

This is a great trail that is now suffering from neglect . The weeds are so overgrown that the trail is almost down to a single lane.

read more …

William R. Steinhaus Dutchess Rail Trail

Top Trail

August, 2024 by z4g9gshqpr

Nice and wide. Plenty of room for walkers, runners and bikers alike. Hudson Valley really has a great series of trails and this is one of them. Connects the Walkway Over the Hudson to the Maybrook Trailway. Bikers dream.

read more …

Ashuwillticook Rail Trail

A top 5 New England trail

August, 2024 by andrix

Lots of wildlife along this pristine trail with plenty for bathroom facilities and benches to take a break. Trail is maybe 70% shaded which kept the temperatures down but still glad we had our suntan lotion. The trail passes a large lake and goes through plenty of wetlands giving lots of interesting views. Road crossings were well marked and safe. Our stay at the Williams Inn in Williamstown was definitely a cut above the norm and from there was maybe a 15 minute drive to the trailhead.

read more …

Albany-Hudson Electric Trail

Nassau to Stuyvesant Falls Park

August, 2024 by andrix

This trail (14 mile section) was in pristine condition with surprising amount of wildlife (herons, deer, turtles) along the way. Park, falls and 1800's mill factory at the southern end was worth a stop. Maybe shaded 50% so suntan lotion a must. There's a parking lot in Nassau right next to the trail. As others have mentioned, very few bathroom facilities on route.

read more …

Mattabassett Trolley Trail

What's the point....

August, 2024 by jbarrett01

......of having a trail where there is nowhere to park???

read more …
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Explore by Activity

ATV
Bike
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Running
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