Trails Near Southold, 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.


Profile
  • 5 miles
  • Colchester, CT

Avalon/East Farm Preserve

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


Profile
  • 2.1 miles
  • Saint James, NY

Belmont Lake State Park

Leisurely ride around a lake.


Profile
  • 3.34 miles
  • North Babylon, 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.


Profile
  • 4 miles
  • Groton, CT

Buckingham Reservoir (Glastonbury Reservoir)

Buckingham Reservoir (Glastonbury Reservoir) is a 2 mile loop trail located near Glastonbury, Connecticut that features a lake and is good for all skill levels. The trail is primarily used for hiking, snowshoeing, trail running & walking and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.


Profile
  • 2 miles
  • Glastonbury, CT

Cathedral Pines

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


Profile
  • 11 miles
  • Brookhaven, NY

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.


Profile
  • 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.


Profile
  • 4.5 miles
  • Weston, CT

East Hartford Loop

Starting from Ramada on 363 Roberts St. Mostly flat urban terrain for first 2.5 mi. Then steep hills and declines for 1.5 mi. Last mile is a straightaway. A good workout if you're ever staying at the Ramada in East Hartford, especially if you see their 'fitness center'.


Profile
  • 5.16 miles
  • East Hartford, CT

Francis C. Carter Memorial Preserve Trail

Francis C. Carter Memorial Preserve Trail is a 4.9 mile loop trail located near Charlestown, Rhode Island 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. Dogs are also able to use this trail but must be kept on leash.


Profile
  • 4.9 miles
  • Charlestown, RI

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.


Profile
  • 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.


Profile
  • 2 miles
  • Madison, 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.


Profile
  • 4.6 miles
  • North Babylon, 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.


Profile
  • 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.


Profile
  • 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.


Profile
  • 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.


Profile
  • 21 miles
  • North Stonington, CT

Nature Trails

White Memorial Foundation: Nature Trails. There are 35 miles of trails on 4000 acres of fields, waters and woodlands. There are also 3 campgrounds, a museum and special areas for large outdoor gatherings.


Profile
  • 7.6 miles
  • Litchfield, 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.


Profile
  • 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.


Profile
  • 3 miles
  • Berlin, 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.


Profile
  • 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.


Profile
  • 1.8 miles
  • Islip, NY

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.


Profile
  • 2.5 miles
  • Kings Park, NY

Tory Den Loop (Mile Of Ledges)

This is a rather difficult loop situated in Burlington, CT off of Greer Road and on the Brower Property. This trail offers some steep inclines with the occasional climb as you walk along the ledges and stop by the tory den. This loop is on part of the Tunxis Mainline Trail and the Yellow Dot trail.


Profile
  • 3 miles
  • Burlington, 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.


Profile
  • 3 miles
  • Hamden, CT

Tri Pond Park

Tri Pond Park is a 2.1 mile loop trail located near Wakefield, Rhode Island that features a lake. The trail is rated as moderate and primarily used for hiking & trail running. Dogs are also able to use this trail but must be kept on leash.


Profile
  • 2.1 miles
  • Wakefield, RI

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.


Profile
  • 11 miles
  • Trumbull, CT

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.


Profile
  • 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.


Profile
  • 15 miles
  • Guilford, CT

Wildwood State Park

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


Profile
  • 12 miles
  • Stony Brook, NY


Free Race Director & Club Services

Use LocalRaces for simple, beautifully designed online event hosting and registration.

  • FREE Secure Online Event Registration
  • FREE Profile Pages
  • FREE Event Management Software
  • FREE Event Marketing Services
Get Started