Trails Near Riverhead, NY

Airline State Park Trail (South)

Airline State Park Trail (South) is a 5 mile point-to-point trail located near Colchester, Connecticut that features a river and is good for all skill levels. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.


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  • 5 miles
  • Colchester, CT

Avalon/East Farm Preserve

This is a great beginner trail run. Clean. Beautiful. Hilly but not too.


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  • 2.1 miles
  • Saint James, NY

Belmont Lake State Park

Leisurely ride around a lake.


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  • 3.34 miles
  • North Babylon, NY

Bethpage Bikeway

A narrow island of nature in Long Island urban sprawl. (7 miles)


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  • 7.32 miles
  • Bethpage, NY

Bluff Point State Park And Coastal Reserve Trail

Bluff Point State Park and Coastal Reserve Trail is a 4 mile loop trail located near Groton, Connecticut that features a great forest setting and is rated as moderate. The trail is primarily used for fishing, hiking, mountain biking & trail running and is accessible year-round.


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  • 4 miles
  • Groton, CT

Cathedral Pines

Beginner to intermediate single track. 6-mile beginner loop with additional 5 miles of optional advanced hill climbs.


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  • 11 miles
  • Brookhaven, NY

Caumsett Mountain Bike Trail

Caumsett Mountain Bike Trail is a 8 mile loop trail located near Huntington, New York that features beautiful wild flowers and is good for all skill levels. The trail offers a number of activity options and is accessible year-round. Horses are also able to use this trail.


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  • 8 miles
  • Huntington, NY

Connecticut Coast Scenic Drive

Connecticut Coast Scenic Drive is a 134 mile point-to-point trail located near Stamford, Connecticut that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.


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  • 134 miles
  • Stamford, CT

Devil'S Den Concourse

Devil's Den Concourse is a 8 mile loop trail located near Weston, Connecticut and is good for all skill levels. The trail is primarily used for hiking & trail running and is accessible year-round.


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  • 8 miles
  • Weston, CT

Devil'S Den Preserve Trail

Devil's Den Preserve Trail is a 7.0 mile loop trail located near Weston, Connecticut and is good for all skill levels. The trail is primarily used for hiking and is accessible year-round.


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  • 4.5 miles
  • Weston, CT

Enchanted Trail

A public trail blazed with diamond-shaped yellow markers that crosses Bethel from Meckauer Park in the north to Huntington Park in the south


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  • Bethel, CT

Great Ledge- Redding Land Trust

Great trail connecting the Nature Conservancy's Devils Den and the Centennial Watershed State Forest's Saugatuck Valley Trail


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  • Redding, CT

Greenport - Orient Point

Greenport - Orient Point is a 21 mile out and back trail located near Shelter Island, New York. The trail is good for all skill levels and primarily used for road biking.


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  • 21 miles
  • Shelter Island, NY

Hammonasset Beach State Park

Hammonasset Beach State Park is a point-to-point trail located near Madison, Connecticut that offers the chance to see wildlife. The trail is good for all skill levels offers a number of activity options. Dogs are also able to use this trail but must be kept on leash.


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  • 2 miles
  • Madison, CT

Hemlock Hills & Pine Mountain

Pine Mountain Reserve is a 368 acre[1] open space in Ridgefield, Connecticut. The space has many trails, trail heads and also one of Ridgefield's highest points, at 1,021 feet (311 m)[2] above sea level.


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  • 0.4 miles
  • Ridgefield, CT

Home Trail

Home trail is a 4.6 mile trail located near North Babylon, New York. The trail is primarily used for trail running.


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  • 4.6 miles
  • North Babylon, NY

John F. Kennedy Memorial Wildlife Sanctuary

John F. Kennedy Memorial Wildlife Sanctuary is a 1.5 mile out and back trail located near Tobay Beach, New York and is good for all skill levels. The trail is primarily used for walking and is accessible year-round. On Ocean Parkway.


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  • 1.5 miles
  • Oyster Bay, NY

Larkin State Bridle Trail

Larkin State Bridle Trail is a 10.3 mile point-to-point trail located near Oxford, Connecticut. The trail is good for all skill levels and primarily used for hiking, mountain biking, trail running & walking. Horses are also able to use this trail.


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  • 10.3 miles
  • Oxford, CT

Meadowlark

Intermediate to advanced single track with many logs to ride over. Tight, twisty and technical terrain with some hills to climb. It's a one way loop, follow blue blazes. Horses may be on fire road crossings, speak up and be courteous.


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  • 3 miles
  • Northport, NY

Millington Trail

Devils Hopyard State Park Trail is a 2.6 mile loop trail located near East Haddam, Connecticut that features a waterfall and is rated as moderate. The trail is primarily used for camping, hiking & trail running and is accessible year-round.


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  • 2.6 miles
  • East Haddam, CT

Narragansett Trail

The Narragansett Trail is a 21-mile route that extends from Lantern Hill in North Stonington, Connecticut, to Ashville Pond in Hopkinton, Rhode Island. It crosses a number of roads so many shorter trips are possible.


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  • 21 miles
  • North Stonington, CT

Nehantic State Forest

The land is mostly covered with a second growth of hardwoods. There are a number of good trout streams in the forest. Paths are wide and generally easy to use. It is extremely quiet and there is a lot of wildlife the further into the forest you travel.


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  • 5 miles
  • East Lyme, CT

Pistol Creek

Pistol Creek is a 3 mile loop trail located near Berlin, Connecticut. The trail is good for all skill levels and primarily used for nature trips, road biking, trail running & walking. Dogs are also able to use this trail.


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  • 3 miles
  • Berlin, CT

Pootatuck State Forest

Hilly terrain with great features.


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  • New Fairfield, CT

Putnam Memorial State Park

This was the site of the Continental Army's 1779 winter encampment under the command of General Israel Putnam. The site consists of remains of the encampment, reconstructed log buildings, and a museum. Connecticut's oldest State Park!


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  • Redding, CT

Shelton Rec Trail

Shelton Rec Trail is a 9.3 mile out and back trail located near Shelton, Connecticut. The trail is rated as moderate offers a number of activity options.


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  • 9.3 miles
  • Shelton, CT

South Shore Nature Center

South Shore Nature Center is a 1.8 mile loop trail located near Islip, New York that offers the chance to see wildlife and is good for all skill levels. The trail is primarily used for hiking, trail running & walking and is accessible year-round.


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  • 1.8 miles
  • Islip, NY

Stillwell Woods Stroll

Stillwell Woods Stroll is a 3.2 mile loop trail located near Woodbury, New York and is good for all skill levels. The trail is primarily used for hiking and is accessible year-round.


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  • 8 miles
  • Woodbury, NY

Strauss & Giddings Preserves

Interconnected land parcels.


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  • Sherman, CT

Sunken Meadow State Park

Sunken Meadow State Park is a 2.5 mile loop trail located near Kings Park, New York that offers the chance to see wildlife and is good for all skill levels. The trail offers a number of activity options and is accessible year-round.


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  • 2.5 miles
  • Kings Park, NY

Tarrywile Park

The Park has over 21 miles of trails, ponds & numerous vistas.


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  • 2.9 miles
  • Danbury, CT

The Mianus Maze

The Mianus Maze is a 14 mile loop trail located near Stamford, Connecticut that features a river. The trail is good for all skill levels offers a number of activity options. Dogs are also able to use this trail but must be kept on leash.


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  • 14 miles
  • Stamford, CT

Topstone Park

topstone park is located near Redding, Connecticut. The trail is good for all skill levels and primarily used for hiking, trail running & walking. Dogs are also able to use this trail but must be kept on leash.


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  • Redding, CT

Tower Trail

Sleeping Giant Tower Trail is a 3 mile out and back trail located near Hamden, Connecticut that offers scenic views and is good for all skill levels. The trail offers a number of activity options and is accessible year-round.


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  • 3 miles
  • Hamden, CT

Trumbull / Old Mine Park

Trumbull / Old Mine Park is a 11 mile loop trail located near Trumbull, Connecticut. The trail runs along the West Branch of the Pequonnock River it is a prime river to catch trophy trout. The trail is primarily used for mountain biking.Dogs are also able to use this trail.


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  • 11 miles
  • Trumbull, CT

Walt Whitman Revisited

Walt Whitman Revisited is a 3.8 mile loop trail located near Huntington, New York and is good for all skill levels. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.


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  • 3.8 miles
  • Huntington, NY

West Woods Ann

West Woods ann is located near Branford, Connecticut and features a lake. The trail is rated as moderate offers a number of activity options. Dogs are also able to use this trail but must be kept on leash.


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  • Branford, CT

Westwoods

Westwoods is a 15 mile loop trail located near Guilford, Connecticut that features beautiful wild flowers and is rated as moderate. The trail is primarily used for hiking, mountain biking & trail running and is accessible year-round. Dogs are also able to use this trail.


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  • 15 miles
  • Guilford, CT

Wildwood State Park

Camping, picnicking, hiking trails used for cross-country skiing in winter, road biking. Beach on LI Sound.


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  • 12 miles
  • Stony Brook, NY


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