Windsor, Connecticut (CT) Trails & Maps

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  • Airline State Park Trail - North

    Rail-Trail

    State: CT
    Length: 27 miles
    Surface: Ballast, Dirt

    The Air Line State Park Trail – North is largely frequented by equestrians, hikers, cross-country skiers and mountain bikers. Start at the Goodwin State Forest Conservation Center off Route 6 in Hampton for the best option. From here to Route ...
  • Airline State Park Trail - South

    Rail-Trail

    State: CT
    Length: 22.4 miles
    Surface: Asphalt, Crushed Stone

    Air Line State Park Trail showcases the engineering behind the Air Line Railroad, laid down through this hilly region in 1873 as a direct route between Boston and New York. As its name implies, the tracks ran flat and straight, like 'a line ...
  • Arkwright Riverwalk

    Rail-Trail

    State: RI
    Length: 1 miles
    Surface: Dirt, Woodchips

    The Arkwright Riverwalk, founded on a former rail bed purchased from Penn Central Railroad, is located in Coventry, a rural central Rhode Island town that was built around textile mills. The one-mile trail includes a wooden boardwalk, but is ...
  • Branford Trolley Trail

    Rail-Trail

    State: CT
    Length: 0.5 miles
    Surface: Concrete, Crushed Stone, Gravel

    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, ...
  • Burrillville Bike Path

    Rail-Trail

    State: RI
    Length: 1.2 miles
    Surface: Asphalt

    Burrillville Bike Path runs for just over a mile through its namesake rural community in northwest Rhode Island. It connects the villages of Pascoag and Harrisville through a corridor that once belonged to the York, New Haven, and Hartford Railroad. ...
  • Canalside Trail

    Rail-Trail

    State: MA
    Length: 3.27 miles
    Surface: Asphalt

    This 3.27 mile trail starting at McClelland Farm Road and heading north on the old NYNH&H RR crosses the Connecticut River near the confluence of the Deerfield and the Connecticut Rivers. The river span here is reported to be one of the oldest ...
  • Charter Oak Greenway

    State: CT
    Length: 9.8 miles
    Surface: Asphalt

    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 ...
  • Cheney Rail Trail

    Rail-Trail

    State: CT
    Length: 1 miles
    Surface: Dirt, Grass, Gravel, Woodchips

    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 ...
  • Chicopee River Canal Rail Trail

    Rail-Trail

    State: MA
    Length: 0.21 miles
    Surface: 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 is lined with tall elm, maple and sycamore ...
  • Columbia Greenway Rail Trail

    Rail-Trail

    State: MA
    Length: 1.5 miles
    Surface: Asphalt

    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 ...
  • Connecticut Riverwalk and Bikeway

    Rail-Trail

    State: MA
    Length: 5.4 miles
    Surface: 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 Bridge in Springfield. Unique features of ...
  • Derby Greenway

    State: CT
    Length: 1.85 miles
    Surface: Asphalt

    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 ...
  • Farmington Canal Heritage Trail

    Rail-Trail

    State: CT
    Length: 40 miles
    Surface: Asphalt, Cinder, Crushed Stone, Grass, Gravel

    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. ...
  • Farmington River Trail

    Rail-Trail

    State: CT
    Length: 14.9 miles
    Surface: Asphalt, Cinder, Crushed Stone, Dirt

    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 ...
  • Grand Trunk Trail

    Rail-Trail

    State: MA
    Length: 4.4 miles
    Surface: Crushed Stone, Gravel

    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 ...
  • Harlem Valley Rail Trail

    Rail-Trail

    State: NY
    Length: 16.1 miles
    Surface: Asphalt, Crushed Stone

    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 ...
  • Hop River State Park Trail

    Rail-Trail

    State: CT
    Length: 18.4 miles
    Surface: Crushed Stone, Dirt, Gravel

    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. ...
  • Housatonic Rail-Trail in Trumbull (Pequonnock Valley Greenway)

    Rail-Trail

    State: CT
    Length: 5 miles
    Surface: Asphalt, Cinder, Crushed Stone

    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 ...
  • Housatonic Valley Rail-Trail in Monroe

    Rail-Trail

    State: CT
    Length: 4.2 miles
    Surface: Asphalt, Crushed Stone

    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 ...
  • Hyde Park Trail

    State: NY
    Length: 10 miles
    Surface: Dirt

    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 ...
  • Kress Family Trail

    Rail-Trail

    State: CT
    Length: 2.5 miles
    Surface: Dirt

    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 ...
  • Larkin State Park Trail

    Rail-Trail

    State: CT
    Length: 10.4 miles
    Surface: Cinder, Crushed Stone, Dirt, Gravel

    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 ...
  • Manhan Rail-Trail

    Rail-Trail

    State: MA
    Length: 9 miles
    Surface: Asphalt

    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 ...
  • Mass Central Rail Trail

    Rail-Trail

    State: MA
    Length: 31.9 miles
    Surface: Crushed Stone, Dirt, Grass

    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 ...
  • Middlebury Greenway

    Rail-Trail

    State: CT
    Length: 4.4 miles
    Surface: Asphalt

    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 ...
  • Moosup Valley State Park Trail

    Rail-Trail

    State: CT
    Length: 5.8 miles
    Surface: Ballast, Crushed Stone, Dirt, Grass, Gravel, Sand

    This 5.8-mile trail is part of the planned East Coast Greenway, an off-road path that will eventually run from Calais, Maine, to Key West, Florida. The Moosup Valley State Park Trail will connect with Rhode Island's Washington Secondary Bike ...
  • Naugatuck River Greenway (Beacon Falls)

    State: CT
    Length: 0.3 miles
    Surface: Asphalt

    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 ...
  • Norwottuck Rail-Trail (Francis P. Ryan Section)

    Rail-Trail

    State: MA
    Length: 4.9 miles
    Surface: Asphalt

    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 ...
  • Norwottuck Rail-Trail (Mass Central Section)

    Rail-Trail

    State: MA
    Length: 10 miles
    Surface: Asphalt

    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 ...
  • Putnam River Trail

    Rail-Trail

    State: CT
    Length: 2 miles
    Surface: 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 Drive, with views of Cargill Falls. The trail ...
  • Quinebaug River Trail

    State: CT
    Length: 4 miles
    Surface: Asphalt

    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 ...
  • Railroad Ramble

    Rail-Trail

    State: CT
    Length: 1.7 miles
    Surface: Asphalt, Dirt, Grass

    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 ...
  • Redstone Rail Trail

    Rail-Trail

    State: MA
    Length: 1.4 miles
    Surface: Asphalt

    The Redstone Rail Trail is built on the former Boston and Maine railroad, the dominate rail line in New England for more than a century. Its name comes from the numerous red sandstone quarries in the area that gave the town its industrial beginnings. On ...
  • Shoreline Greenway Trail

    State: CT
    Length: 2.3 miles
    Surface: Crushed Stone

    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 ...
  • Southern New England Trunkline Trail

    Rail-Trail

    State: MA
    Length: 21 miles
    Surface: Ballast, Crushed Stone

    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 Railroad's Midland Division, which operated between Boston ...
  • Southwick Rail Trail

    Rail-Trail

    State: MA
    Length: 7.1 miles
    Surface: Asphalt

    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 ...
  • Stratton Brook State Park Trail

    Rail-Trail

    State: CT
    Length: 1.2 miles
    Surface: Asphalt, Cinder, Crushed Stone

    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 ...
  • Sue Grossman Still River Greenway

    Rail-Trail

    State: CT
    Length: 2.9 miles
    Surface: Asphalt

    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 ...
  • Trolley Trail (CT)

    Rail-Trail

    State: CT
    Length: 0.75 miles
    Surface: Asphalt

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

    Rail-Trail

    State: CT
    Length: 4 miles
    Surface: Crushed Stone

    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 ...
  • Ware River Rail-Trail

    Rail-Trail

    State: MA
    Length: 12 miles
    Surface: Ballast, Dirt, Grass, 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 an informal basis from the outskirts of ...
  • Windsor Locks Canal State Park Trail (WIndsor Locks Canal Towpath)

    State: CT
    Length: 4.5 miles
    Surface: Asphalt

    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. ...
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