Connecticut - Outdoor Activities

Connecticut has approximately 1,164 trails, including 935 hiking trails and 668 for walking. These trails range from 0 to 201 miles in length. The most popular trails are Bear Mountain, The Weir Preserve and Ragged Mountain Preserve Trail. The last Trails.com member to complete a trail in Connecticut was Ashish G. who completed Ragged Mountain Preserve Trail.

  • Bear MountainView Trail Details

    16 Reviews

    Salisbury, CT

    • Hiking  
    •  3.5–4.5 hours
    •  6 miles
    •  Guide

    From the parking area, pale-blue-blazed Undermountain Trail immediately passes a kiosk on the right with a posted map; trail maps are sometimes ...

  • Ragged Mountain Preserve TrailView Trail Details

    11 Reviews

    Berlin, CT

    • Hiking  
    •  6.1 miles
    •  Guide

    Located in Berlin, CT. Within this 563-acre open space acquired through the Land and Water Conservation Fund, a demanding loop journeys through ...

  • Mount FrissellView Trail Details

    11 Reviews

    Salisbury, CT

    • Hiking  
    •  3.5–4.0 hours
    •  5.2 miles
    •  Guide

    From the parking area on East Street (called Mount Washington Road in Connecticut), near the Connecticut–Massachusetts state line, red-blazed ...

  • Zoar TrailView Trail Details

    10 Reviews

    Stevenson, CT

    • Hiking  
    •  6.5 miles
    •  Guide

    In Lower Paugussett State Forest, on the west shore of Lake Zoar, this blue-blazed loop applauds lake and woods, with a side trip to a waterfall. ...

  • The Weir PreserveView Trail Details

    9 Reviews

    Wilton, CT

    • Hiking  
    •  1.0 hour
    •  1.1 miles
    •  Guide

    Enter the preserve, owned by the Weir Farm Art Center—a private, nonprofit organization that supports Weir Farm National Historic Site—on a wide ...

  • Lion’s HeadView Trail Details

    8 Reviews

    Salisbury, CT

    • Hiking  
    •  1.5–2.0 hours
    •  1.9 miles
    •  Guide

    From the northeast corner of the parking area, follow the gravel path north through a field of sensitive fern, goldenrod, and isolated islands ...

  • People’s State ForestView Trail Details

    6 Reviews

    Winsted, CT

    • Hiking  
    •  3.0–4.0 hours
    •  4.7 miles
    •  Guide

    Jesse Gerard Trail (blazed yellow on blue) begins at a sign across the road from the parking area; here, trail maps are sometimes available. ...

  • Macedonia Brook State ParkView Trail Details

    6 Reviews

    Kent, CT

    • Hiking  
    •  6.8 miles
    •  Guide

    A demanding loop travels the east and west ridges framing the Macedonia Brook drainage. Special attractions: Vistas, ridge and valley forests, ...

  • Devil's Den PreserveView Trail Details

    6 Reviews

    Redding, CT

    • Hiking  
    •  7.2 miles
    •  Guide

    In Weston and Redding. A broad-swinging loop travels several of the named trails, touring much of the preserve; side spurs visit granite ledges ...

  • The Mianus MazeView Trail Details

    6 Reviews

    Greenwich, CT

    • Mountain Biking  
    •  14 miles
    •  Guide

    This unique trail system, located in the Mianus River Park near Greenwich, Connecticut, is a maze of singletrack and hard-packed old carriage ...

  • Wolcott Trail and Burr PondView Trail Details

    6 Reviews

    Winsted, CT

    • Hiking  
    •  1.5 hours
    •  2.75 miles
    •  Guide

    From the parking lot, follow the light-blue-blazed Wolcott Trail—named for the Civilian Conservation Corps’ Camp Wolcott—north (counterclockwise) ...

  • Mile of Ledges and Tory DenView Trail Details

    5 Reviews

    Bristol, CT

    • Hiking  
    •  2.0–2.5 hours
    •  4.25 miles
    •  Guide

    As part of the Bristol public water supply, the area is posted against trespassing, but hikers are welcome. From the metal gate, follow the level ...

  • Metacomet Trail, Talcott MountainView Trail Details

    5 Reviews

    Bloomfield, CT

    • Hiking  
    •  19.5 miles
    •  Guide

    Three miles west of Bloomfield. This segment of the long-distance Metacomet Trail tours the rolling ridge of Talcott Mountain, topping rock ...

  • Sleeping Giant State ParkView Trail Details

    5 Reviews

    New Haven, CT

    • Hiking  
    •  6 miles
    •  Guide

    Eight miles NE of New Haven. The two hiking loops chosen to represent this award-winning trail system travel mixed hardwood forest and picturesque ...

  • Indian Council CavesView Trail Details

    5 Reviews

    Barkhamsted, CT

    • Hiking  
    •  2.0–3.0 hours
    •  4.6 miles
    •  Guide

    From the parking lot, proceed north across CT 219, step over the cable guardrail, and enter woods of tulip tree, red oak, maple, hemlock, and ...

  • Talcott MountainView Trail Details

    5 Reviews

    Bristol, CT

    • Hiking  
    •  3.0–3.5 hours
    •  3.3 miles
    •  Guide

    Tower Trail begins on the left side of the access road, about 1,000 feet from the CT 185 entrance, but a less crowded feeder path begins at the ...

  • Sessions Woods Wildlife Management AreaView Trail Details

    5 Reviews

    Bristol, CT

    • Hiking  
    •  3.0–4.0 hours
    •  3 miles
    •  Guide

    A gazebo at the far end of the lot contains property information. Beaver Pond trailhead, however, is located at the end of the wide graveled ...

  • Selden Neck CampgroundView Trail Details

    4 Reviews

    Haddam, CT

    • Campgrounds  
    •  Guide

    There is absolutely no way you’ll find an RV at the Selden Neck Campground, in Gillette Castle State Park. It has no designated tent-only areas, ...

  • Trumbull / Old Mine ParkView Trail Details

    4 Reviews

    Trumbull, CT

    • Mountain Biking  
    •  11 miles
    •  Guide

    Just north of the town of Trumbull, off Connecticut Highway 25. The terrain is flat, except for a short, steep climb on a loose gravel jeep road ...

  • Gay City State ParkView Trail Details

    4 Reviews

    Manchester, CT

    • Hiking  
    •  5 miles
    •  Guide

    Five miles SW of Manchester. Two circuits explore the park's woods, wetlands, and history, traveling both woods road and foot trail. Special ...

  • Pine Knob Loop TrailView Trail Details

    4 Reviews

    Sharon, CT

    • Hiking  
    •  1.5–2.5 hours
    •  2.6 miles
    •  Guide

    From the parking area, follow light-blue blazes within a mixed grove of sugar maples. The trail enters a shady woodland with an herb layer of ...

  • Hanging HillsView Trail Details

    4 Reviews

    Meriden, CT

    • Hiking  
    •  4 miles
    •  Guide

    The blue-blazed Metacomet Trail passes over the peaks of the Hanging Hills of Meriden. West Peak, with an elevation of 1,024 feet, offers one ...

  • Bear RockView Trail Details

    3 Reviews

    Higganum, CT

    • Hiking  
    •  1.0 hour
    •  1 miles
    •  Guide

    From the pull-off, near a small pond where spring peepers sing in April, head north uphill on the blue-blazed Mattabesett Trail (part of the ...

  • Ratlum MountainView Trail Details

    3 Reviews

    New Hartford, CT

    • Hiking  
    •  7 miles
    •  Guide

    This walk along the Tunxis Trail begins near the midpoint of Ratlum Road, which begins in New Hartford and ends in Barkhamsted. From the summit, ...

  • Madison - HammonassetView Trail Details

    3 Reviews

    Madison, CT

    • Road Biking  
    •  17 miles
    •  Guide

    Madison is often called a bedroom town for New Haven, but only by those who don’t live there. It not only is a beautiful New England small town ...

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