27 results
    2

    13th Delaney Dash

    Sat, May 25 @ 2 Bridge St, Old Saybrook, CT    

    4-Mile, Flat, Fast (CT09025JHP) Course. USATF-CT Grand Prix 4-mi Championship coolrunning.com

    3

    Airline State Park Trail - South

    North Westchester, CT    

    5 out of 5 based on 4 ratings

    Panoramic views of the surrounding Connecticut hills and valleys characterize the Airline State Park Trail. Its most dramatic features are its two hidden viaducts, which offer expansive views of the scenery below. Surface: Or... trails.com

    4

    Cedar Point County Park

    Cedar Point Rd, East Hampton, NY     (631) 852-7620

    5 out of 5 based on 2 ratings

    Steeped in history, Cedar Point County Park offers a vast campground, sweeping views of Gardiner's Bay and a rocky beach that leads to the historic Cedar Point Lighthouse. First settled in 1651, that area of Northwest Woods wa... patch.com

    5

    Coginchaug Cave, Durham, Connecticut

    Durham, CT    

    0 out of 5 based on 0 ratings

    A difficult hike, this one will have you a bit winded once you get to the top. It?s worth the trip, though; especially on a hot summer day as your destination is a cool and shaded ?cave? with lots of history to contemplate. trails.com

    6

    Day Pond - Salmon River, Colchester, Connecticut

    North Westchester, CT    

    0 out of 5 based on 0 ratings

    In colonial times the Day family created a pond to provide water for a sawmill, where they turned chestnut, maple, and oak logs into lumber. By the 1870s horses were hauling wagons across a covered bridge over the nearby Salm... trails.com

    7

    Chatfield Trail, Killingworth, Connecticut

    Madison, CT    

    0 out of 5 based on 0 ratings

    The entire Chatfield Trail is about 4.3 miles long, but our walk goes only to Champlin Road, a gravel road that crosses the trail less than 2 miles from the start. Most woods trails, depending upon the amount of moisture, are... trails.com

    8

    Bluff Point State Park

    Depot Rd, Groton, CT     (860) 444-7591

    4 out of 5 based on 80 ratings

    Voted Best Getaway in Connecticut by Connecticut Magazine in 2000, Bluff Point State Park and Coastal Reserve does not disappoint. Here you can explore an almost 4-mile loop trail through woodlands, wetlands, and shoreline as... trails.com

    9

    Trolley Trail, Branford, Connecticut

    Branford, CT    

    4 out of 5 based on 1 ratings

    A gem of a walk and a paradise for bird watchers, the Stony Creek Trolley Trail between the Pine Orchard and Stony Creek sections of Branford is suitable for all ages and abilities. The entire round-trip is less than 2 miles.... trails.com

    10

    Reservoir Loop, Middletown, Connecticut

    Middle Haddam, CT    

    0 out of 5 based on 0 ratings

    This pleasant, easy trail offers a little bit of everything: great views, varied environments, even an old quarry. trails.com

    11

    Orient Town Walk, Greenport, New York

    East Marion, NY    

    0 out of 5 based on 0 ratings

    Places on earth, like people, seem to develop under current conditions along conforming lines. One airport looks pretty much like any other, anywhere in our world, and cities and houses fall into similar categories. Those pla... trails.com

    12

    Mashomack Preserve, Shelter Island, New York

    Shelter Island, NY    

    0 out of 5 based on 0 ratings

    Mashomack is unique. In its 2,000 acres of woodlands, marshes, and tidal creeks, it provides a greater variety of habitats and a greater variety of birds than any other area on Long Island. Walking on some of the 20 miles of ... trails.com

    13

    Niantic Bay Triathlon

    Sun, Aug 4 @ Columbus Ave, Niantic, CT    

    1/2 mile swim, 12 mile bike, 3.5 mile run coolrunning.com

    14

    Branford Trolley Trail

    Branford, CT    

    5 out of 5 based on 1 ratings

    Overview Photos Reviews Nearby traillink.com

    15

    Horton Pt

    Southold, NY    

    0 out of 5 based on 0 ratings

    The Horton Point Lighthouse sits serenely atop a 110-foot bluff, looking something like a canvas by Edward Hopper, over the waters of Long Island Sound facing Connecticut. It was once part of the extensive land allotment of B... trails.com

    16

    Bluff Head, Guilford, Connecticut

    Durham, CT    

    4 out of 5 based on 1 ratings

    Don your sturdy hiking boots, pack a pair of binoculars, and head for Totoket Mountain?s Bluff Head on a bright, clear day. Much of this trail flirts with the edge of the steep cliff, affording dizzying views but creating pro... trails.com

    17

    Orient Beach State Park

    Rte 25, Orient, NY     (631) 323-2440

    4 out of 5 based on 4 ratings

    Orient Point looks to the northeast, but this narrow strip of land that is Orient Beach, 4 miles long, runs to the southwest. What makes it unusual? It affords beautiful views of Gardiners Bay and its shores and islands. Wand... trails.com

    18

    Coast Guard Triathlon

    Sun, Aug 25 @ New London, CT    

    Olympic distance triathlon coolrunning.com