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Plainville, Connecticut Trails and Maps

Looking for the best trails around Plainville, Connecticut? Find the top rated trails in Plainville, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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TRAIL LENGTH SURFACE TRAIL MAP

Air Line State Park Trail

53.6 miles
Air Line State Park Trail winds for 53 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state border, you can make a contiguous connection to the ...
Gravel

Branford Trolley Trail

0.5 miles
The Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a marsh habitat that is home to many shorebirds, ...
Concrete
Crushed Stone
Gravel

Briarcliff-Peekskill Trailway

12 miles
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 orginally acquired in 1929 by the Westchester Parkway ...
Asphalt
Dirt
Grass

Charter Oak Greenway

9.8 miles
The Charter Oak Greenway is a paved, multi-use trail connecting parks and the Captain John Bissell Greenway in East Hartford with residential and commercial areas. The trail runs for 9.8 miles between Forbes Street in East Hartford and Porter ...
Asphalt

Cheney Rail Trail

1 miles
The Cheney Rail Trail follows part of the corridor of the South Manchester Railroad, built by the Cheney brothers in 1869. The line was a 2.5-mile spur from the main Hartford, Providence, and Fishkill Railroad and it went to the Cheney silk ...
Crushed Stone

Chicopee River Canal Rail Trail

0.21 miles
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 is lined with tall elm, maple and sycamore ...
Asphalt

Columbia Greenway Rail Trail

1.5 miles
Columbia Greenway Rail Trail currently offers 1.5 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. When completed, the trail will stretch just over 3 miles from the Great River Bridge over the Westfield River ...
Asphalt

Connecticut Riverwalk and Bikeway

5.4 miles
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 Bridge in Springfield. Unique features of ...
Asphalt

Derby Greenway

1.85 miles
The Derby Greenway runs between Division Street and Main Street, paralleling the Naugatuck and Housatonic rivers. The trail runs on top of a flood control dyke for the rivers; a portion of it goes across O'Sullivan's Island. One of the centerpieces ...
Asphalt

Farmington Canal Heritage Trail

40 miles
Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles from New Haven to Northampton, Massachusetts. ...
Asphalt
Cinder
Crushed Stone
Grass
Gravel

Farmington River Trail

14.9 miles
The Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A short disconnected section of trail extends between ...
Asphalt
Cinder
Crushed Stone
Dirt

Grand Trunk Trail

4.4 miles
Grand Trunk Trail is part of a larger trail network, the Titanic Rail Trail, which will stretch more than 60 miles through south-central Massachusetts and the northeastern corner of Connecticut along the former Southern New England Railroad. The ...
Crushed Stone
Gravel

Harlem Valley Rail Trail

16.1 miles
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is being built in segments, and there is still ...
Asphalt
Crushed Stone

Hop River State Park Trail

18.4 miles
Hop River State Park Trail is one of Connecticut's top rail-trails. Narrow cuts and a lush tree canopy make for enjoyable visits year-round. Most of the route, from the Manchester–Vernon town line to Hop River Road, follows a crushed stone surface. ...
Crushed Stone
Dirt
Gravel

Housatonic Rail-Trail in Trumbull (Pequonnock Valley Greenway)

5 miles
The Housatonic Rail-Trail in Trumbull, a.k.a., the Pequonnock Valley Greenway, offers a shady respite from suburban Trumbull, this fairly flat trail overlooks the winding Pequonnock River for much of its 3.4 miles. Rapids and distinctive rock ...
Asphalt
Cinder
Crushed Stone

Housatonic Valley Rail-Trail in Monroe

4.2 miles
The Housatonic Rail-Trail in Monroe is a northern continuation of the Trumbull segment of the rail-trail. Locals refer to it as the Monroe Housatonic Railbed Trail. The 4.3-mile trail is largely forested and is a convenient bike route to William ...
Asphalt
Crushed Stone

Hyde Park Trail

10 miles
The Hyde Park Trail is a 10-mile system connecting national historic sites, town parks and nature preserves in Hyde Park, New York. The trail connects the national historic sites of Vanderbilt Mansion, Home of Franklin D. Roosevelt, and Eleanor ...
Dirt

Kress Family Trail

2.5 miles
The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, 2.5-mile trail is popular with cross-country skiers and snowshoers in winter, while hikers enjoy the trail during the ...
Dirt

Larkin State Park Trail

10.4 miles
Canopied with deciduous trees for most of its 10.4 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse residential development. Its railroad past began ...
Cinder
Crushed Stone
Dirt
Gravel

Manhan Rail-Trail

9 miles
The Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce and community, as well as historical and ...
Asphalt

Mass Central Rail Trail

31.9 miles
A 104 mile rail line was shattered by hurricane in 1938. Now, more than 60 years later, dedicated volunteers in 33 communities are working to reconnect it. Instead of trains there will be cross-country skiers, bicyclists, hikers, and joggers. It ...
Crushed Stone
Dirt
Grass

Maybrook Trailway

3.7 miles
Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of the Beacon Line, a two part railroad from ...
Asphalt

Middlebury Greenway

4.4 miles
The delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an off-road option for running errands and welcomes ...
Asphalt

Naugatuck River Greenway (Beacon Falls)

0.3 miles
The Naugatuck River Greenway segment in Beacon Falls offers a short, but scenic route along the river that is paved and well-lighted. Just north of the trail's end at the Depot Street Bridge, lies Volunteer Park, a pleasant place to stop and ...
Asphalt

Norwalk River Valley Trail

4.3 miles
When completed, the Norwalk River Vally Trail will run from Long Island Sound to Danbury, about 27 miles. To date, disjointed sections are complete in Norwalk and Wilton.
Asphalt

Norwottuck Rail-Trail (Francis P. Ryan Section)

4.9 miles
In central Massachusetts, the Norwottuck Rail-Trail (formerly the Northampton Bikeway) runs between New South Street in Northampton and the neighborhood north of Look Memorial Park in Florence. Whether you start your trip from either trailhead ...
Asphalt

Norwottuck Rail-Trail (Mass Central Section)

10 miles
Caution: As of July 2013, the Massachusetts Department of Transportation (MassDOT) and Department of Conservation and Recreation (DCR) are working together to rehabilitate the Norwottuck Rail Trail from Northampton to Belchertown. The work will ...
Asphalt

Old Croton Aqueduct Trail

26.1 miles
The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has been designated a National Historic Landmark. ...
Asphalt
Concrete
Dirt

Old Mine Railroad Trail

2.2 miles
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 expanded to include almost 10,000 acres of ...
Dirt

Putnam Trailway

11 miles
The final passenger cars of the Putnam Division of the New York Central Railroad ran in 1958, but the rail line that so influenced development of this area still sparks nostalgia. The "Old Put" carried commuters from New York City north to Brewster, ...
Asphalt

Quarry Trail

0.1 miles
The Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic Park and Hastings-on-Hudson trails. Access ...
Dirt
Grass

Quinebaug River Trail

4 miles
As of January 2012 the Quinebaug River Trail has two segments. The southern segment follows the course of the Quinebaug River in Danielson, beginning at the intersection of Palmer Street and Prospect Avenue, crossing a bridge over Fivemile Pond ...
Asphalt

Railroad Ramble

1.7 miles
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 the recreational complex. You'll have to climb ...
Asphalt
Dirt
Grass

Redstone Rail Trail

1.4 miles
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 red sandstone quarries in the area that gave ...
Asphalt

Ridgefield Rail Trail

2.3 miles
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 of the town's parks and open spaces, including ...
Gravel

Shoreline Greenway Trail

2.3 miles
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, the trail will connect parks, schools, town ...
Crushed Stone

Southwick Rail Trail

7.1 miles
The Southwick Rail Trail is now complete from the Massachusetts–Connecticut state line, where it continues south as the Farmington Canal Heritage Trail. On the north end, the trail extends to the Westfield town line and connects to the Columbia ...
Asphalt

Stratton Brook State Park Trail

1.2 miles
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 park also offers picnic areas, as well as ...
Asphalt
Cinder
Crushed Stone

Sue Grossman Still River Greenway

2.9 miles
The Sue Grossman Still River Greenway runs for nearly 3 miles through a wooded corridor between Lanson Drive and Harris Drive in Torrington. The paved trail occupies the old right-of-way for the New York, New Haven, and Hartford Railroad's Naugatuck ...
Asphalt

Trolley Trail (CT)

0.75 miles
The Trolley Trail runs through Plainfield and is a key link the East Coast Greenway. Plans are to use this trail as a link between the Moosup Valley State Park Trail and the Airline State Park Trail.
Asphalt

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)

4 miles
Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns and lichen. Crossing a wooded terrain of ...
Crushed Stone

William R. Steinhaus Dutchess County Rail Trail

13 miles
The Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green landscape of dense tree cover, linking Poughkeepsie at the Hudson River ...
Asphalt

Windsor Locks Canal State Park Trail (WIndsor Locks Canal Towpath)

4.5 miles
The 4.5-mile Windsor Locks Canal Trail follows the Connecticut River and the Windsor Locks Canal between Windsor Locks and Suffield. This trail provides scenic views of the river and canal, and the corridor is home to a variety of wildlife. ...
Asphalt