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Greenport, New York (NY) Trails and Maps

Looking for the best trails around Greenport, New York? Find the top rated trails in Greenport, 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

Arkwright Riverwalk

1 miles
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 ...
Dirt
Woodchips

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

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

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

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

Kings Park Hike & Bike Trail

1.5 miles
The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an abandoned railroad corridor that was once an old ...
Asphalt

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

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

Moosup Valley State Park Trail

5.8 miles
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 ...
Ballast
Crushed Stone
Dirt
Grass
Gravel
Sand

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

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

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

William C. O'Neill Bike Path

6.8 miles
Named for the late state senator who spearheaded development of the trail, the William C. O'Neill Bike Path (a.k.a. South County Bike Path) follows the route of the former Narragansett Pier Railroad, which connected the coastal village of South ...
Asphalt