The Best Trails in Connecticut (United States)

2,060 trails

(20)
  • Basic Loop

    Mountain Bike
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    near Highland Park, Connecticut (United States)
    Distance
    8.09mi
    Elevation +
    1860f
    TrailRank
    16

    Case Mountain in MANCHESTER, CT This is a common loop for case mountain. Starting at Spring Street, it goes out to Sawmill Road, over to the Shenipset Trail for a bit, and loops up and over Birch Mountain and back. Th...

  • Mt. Frissell

    Hiking
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    near Alander, Massachusetts (United States)
    Distance
    3.19mi
    Elevation +
    1227f
    TrailRank
    16

    Great hike! If you follow the trail we did you can stand in two states at once and if you keep going you will hit a marker and be able to stand in 3 states at once!

  • S. Mass N Ct 65 loop

    Road Bike
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    near Ware, Massachusetts (United States)
    Distance
    68.30mi
    Elevation +
    4721f
    TrailRank
    16

    I did this ride 6-4-11 immediately after the devastating tornado of June 1st. I was awestruck at the damage in Monson and Brimfield

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  • Ridge Trail - West Mountain

    Hiking
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    near Firetown, Connecticut (United States)
    Distance
    3.62mi
    Elevation +
    627f
    TrailRank
    16

    This is the whole trail from route 309 to Firetown Rd. Or vice versa... Some portions are very hard to follow. Use gps...

  • Trumbull Loop

    Mountain Bike
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    near Trumbull, Connecticut (United States)
    Distance
    4.67mi
    Elevation +
    610f
    TrailRank
    16

    E Moneybags showed us around. From what I understand this is his standard route - and it is damn fun. This ride is under 5 miles, with not much climbing at all - but damn, this was a fun fun ride. Trumbull is cool.

  • Early Burner

    Unspecified
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    near Lakeridge Heights, Connecticut (United States)
    Distance
    10.55mi
    Elevation +
    1076f
    TrailRank
    16

    Checks in a little under 11 miles. But its 11 miles of sweet twisty rocky singletrack. Oh my. Felt me a lot of burning in the legs (for a change) throughout, but hot damn this was a darn tootin good ride. I recommend.

  • Windham-Manfield-Coventry-Windham

    Mountain Bike
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    near Willimantic, Connecticut (United States)
    Distance
    26.52mi
    Elevation +
    1158f
    TrailRank
    16
    Photo ofWindham-Manfield-Coventry-Windham Photo ofWindham-Manfield-Coventry-Windham Photo ofWindham-Manfield-Coventry-Windham

    Circular route around these 3 towns. It's not a difficult route but there are some slopes. Most of the route are roads with bike path, trails or not busy roads.

  • 2014 Summer Vacation

    Bicycle Touring
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    near Woods at Sweetwater, Pennsylvania (United States)
    Distance
    424.18mi
    Elevation +
    9232f
    TrailRank
    15

    Start in Gradyville, PA 1st stop: Metuchen, NJ 2nd stop: Norwalk, CT 3rd stop: New London, CT 4th stop: Coverntry, RI 5th stop: Boston, MA Bike used: 2011 Boardman Hybrid Team

  • near Crystal Lake, Connecticut (United States)
    Distance
    0.12mi
    Elevation +
    30f
    TrailRank
    15
    Photo ofStoppleworth Conservation Area (CT)

    This is one of many conservation Areas located in Tolland Connecticut. I didn't get a chance to do the actual trails, but I wanted to at least show you where it is and what is available for just stopping at this spot. Th...

  • near Crystal Lake, Connecticut (United States)
    Distance
    1.16mi
    Elevation +
    289f
    TrailRank
    15
    Photo ofCampbell's Peaceful Valley Conservation Area (CT)

    This is one of the many conservation areas found in Tolland Connecticut. The trails are very well laid out and visitor friendly. This hike will take you up a pretty steep grade to a rock which will give you a very pictur...

  • Knofla Conservation Area (CT)

    Hiking
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    near Crystal Lake, Connecticut (United States)
    Distance
    2.16mi
    Elevation +
    407f
    TrailRank
    15
    Photo ofKnofla Conservation Area (CT)

    One of many conservation areas found in Tolland Connecticut. This is a very nice trail to get out and see what nature in this part of the state has to offer. We did some GEOCaching in the area, which added that much more...

  • near Wapping Mews Elderly Housing, Connecticut (United States)
    Distance
    1.56mi
    Elevation +
    745f
    TrailRank
    15

    The South Windsor Wildlife Sanctuary is an interesting place to visit. There are a number of trails that crisscross the property. They are not blazed, but very worn in. The trail system winds through many habitats, inclu...

  • McCann Family Farm (CT)

    Hiking
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    near Somers, Connecticut (United States)
    Distance
    3.05mi
    Elevation +
    1594f
    TrailRank
    15

    The McCann Family Farm is a land trust that has very nice blazed trails. It is well kept up, with bridges and boardwalks where necessary. As of 2014 it was only open to the public on weekends and holidays. The adjusting ...

  • near Brooklyn, Connecticut (United States)
    Distance
    1.58mi
    Elevation +
    531f
    TrailRank
    15

    This is just one of the trail systems found in Brooklyn CT. The main entrance is located just below the Donald Francis Recreation Park. A small bridge can be found there to cross a small, pretty brook. The trails wind th...

  • near Amesville, Connecticut (United States)
    Distance
    18.02mi
    Elevation +
    4534f
    TrailRank
    15

    This is just a reconstruction of the route of a weekend hike I did with the AMC on the AT in CT and MA. These are NOT tracks. The AT map that comes with the Appalachian Trail Conference booklet puts the hike at more like...

  • near Westchester, Connecticut (United States)
    Distance
    1.17mi
    Elevation +
    272f
    TrailRank
    15

    This hike will take you onto the beautiful trails found in the Day Pond State Park. All the trails are well blazed, which is extra special. We did GEOCaching along the trails, which adds that much more to the hike. I alw...

  • near State Line, Massachusetts (United States)
    Distance
    2.83mi
    Elevation +
    479f
    TrailRank
    15

    This hike will take you into a section of Shenipsit State Forest seldom used. It mainly is a road/trail hike, but we did venture off onto what might someday be a new blue blazed trail. There is a scout camp located along...

  • near Bolton, Connecticut (United States)
    Distance
    2.11mi
    Elevation +
    108f
    TrailRank
    15

    This hike will take you out a ways on the orange blazed trail. We parked at a picnic area at the trailhead. There was a restroom right near the parking area. You will be close to the remnants of some of the old mills whi...

  • Morey Pond Trails (Conn)

    Hiking
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    near Union, Connecticut (United States)
    Distance
    1.03mi
    Elevation +
    344f
    TrailRank
    15

    This hike will take you along Morey Pond. This area has a rich history, starting in 1934 when the Civilian Conservation Corps (CCC) created the area for local activities. There still are remnants of their work - very old...

  • Nipmuck State Forest Trail (Conn)

    Hiking
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    near Staffordville, Connecticut (United States)
    Distance
    0.89mi
    Elevation +
    233f
    TrailRank
    15

    This trail is marked as a snowmobile trail, but is is a fine hiking trail. There are some GEOCaches along it, so you can get those. The trail does cross the main road at one point, so be careful. There is a nice bridge c...

  • near Andover, Connecticut (United States)
    Distance
    3.04mi
    Elevation +
    518f
    TrailRank
    15

    This hike will take you on a section of the Hop River Trail towards Williamantic. The Hop River Trail is an old railroad bed converted to a bike & walking trail. It is a beautiful place to visit. I have only been on the ...

  • Whitaker Woods Trails (CT)

    Hiking
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    near Somers, Connecticut (United States)
    Distance
    2.26mi
    Elevation +
    1578f
    TrailRank
    15

    Whitaker Woods Trails are well blazed and easy to follow. They cross streams, wind up hills, cut through old stone walls and pass through many areas of beautiful ferns. I did the hike in the summer time, but I’m sure hik...

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