Wolcott, Connecticut

Looking for the best hiking in Wolcott? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Wolcott. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Wolcott

  • Sharon, Connecticut

    Hike the Pine Knob Loop, Housatonic Meadows SP

    5.0
    2.5 mi / 770 ft gain
    The Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick  woods filled with vistas, wild flowers and tons of wild life.  You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...
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  • New Fairfield, Connecticut

    Hike Squantz Pond Trail

    2.2 mi / 321 ft gain
    The hike is rated as moderate and is accessible all year round. While it’s accessible during all seasons, the sights of the leaves changing colors in the autumn makes it an exceptionally beautiful time to do this hike. You’ll definitely want to snap some photos along the way of the foliage reflec...
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  • Glastonbury, Connecticut

    Blackledge Falls

    4.0
    1.46 mi / 207 ft gain
    Although the park contains hiking trails, a pond and a streambelt, the primary draw of this parcel of land is the 25 foot waterfall. The falls flow varies depending on the volume of precipitation, from a trickle in the dry months to a three-pronged vertical drop after some consistent snow melt or...
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  • Danbury, Connecticut

    Hike Middle Mountain To Thomas Mountain Loop

    3.7 mi / 856 ft gain
    Middle Mountain to Thomas Mountain Loop is a 3.7 mile loop hike that takes you past great forest setting located near Danbury, Connecticut.
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  • Kent, Connecticut

    Hike the Ridge Loop Trail, Macedonia Brook SP

    3.0
    For a quick weekend trip from Newport, RI, Macedonia Brook State Park had a lot to offer for its size. In three or four hours, with lunch, you can hike the 6.4 mile ridge trail and get some fresh air without having to hike on too busy of trails. The elevation gain is only around 700 ft, however, ...
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  • Canaan, Connecticut

    Explore Great Falls

    3.0
    0.5 mi
    Stumbled upon Great Falls in the Falls Village section of Canaan, CT. The stunning 50ft waterfall doesn't disappoint. very easy hike from parking lot, you must cross the river in order to get close for bottom view. Hop on top of turtle rock and relax as the waterfall tumbles in the distance.
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  • Ridgefield, Connecticut

    Hike the Hemlock Hills & Pine Mountain Loop

    5.0
    7.5 mi / 1174 ft gain
    There are several trailheads for Hemlock Hills But the least crowded is at the intersection of Ned's Mountain road and Bogus Road.  I took my 3 year old black lab. There are ton's of little ponds for your dog to jump in and do dog things.  For the most part the hike is flat but at some parts it c...
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  • Dover Plains, New York

    Hike Dover's Stone Church

    4.5
    Dover Stone Church has been a beautiful and popular destination in the Hudson Valley for some time, and recently the park purchased a new parcel of land and added three trails through the nearby woods. But the gem of the park is, and always will be, the impressive cave with the creek and waterfal...
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  • Norfolk, Connecticut

    Campbell Falls

    4.0
    0.99 mi / 161 ft gain
    Campbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....
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  • Bridgeport, Connecticut

    Stroll around Fayerweather Island

    0.5 mi
    Parking is at the end of Barnum Road in the Seaside Park.  Though the lighthouse grounds are accessible the tower itself is not open to the public.  To access the island you must walk across the breakwater.  Please use caution as it is uneven footing and at times can be slippery.  From the isla...
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  • East Haddam, Connecticut

    Chapman Falls

    4.0
    0.55 mi / 49 ft gain
    If you map to Chapman Falls in East Haddam, CT, you will be brought to a parking lot opposite from the waterfall in Devil's Hopyard, a beautiful Connecticut state park. Once there, it's only a few minute walk down a very clear trail to the base of the 60 foot falls.  There's plenty of room to se...
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  • Sandisfield, Massachusetts

    Buck River Swimming Hole

    4.0
    0.3 mi / 250 ft gain
    This swimming hole is 7-feet deep. At the top of the swimming hole is a 12-foot waterfall with slide down. Parking: The swimming hole is located between Sandisfield Town Office and the post office. There is one dirt pull-off space near the swimming hole. The easiest parking is at the Town Offic...
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  • Salisbury, Connecticut

    Explore Riga Falls

    The best part of the adventure is finding this hidden gem also known as Riga Falls. Riga Falls is actually one of Connecticut's lesser known waterfalls, but arguably the most scenic. A helpful hint is that the waterfall lies beside dirt road, keep your ears open! I've already said too much, happy...
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  • Salisbury, Connecticut

    Bear Mountain Loop

    4.7
    6.05 mi / 1516 ft gain
    At 2,316 feet, Bear Mountain is the highest peak in Connecticut. The peak is about a half-mile south of the Massachusetts state line on the Appalachian Trail. The views are great. On a clear day you can see some of the peaks in southern New Hampshire. The remnants of a stone tower are on the summ...
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  • Carmel Hamlet, New York

    Ninham Mountain Fire Tower

    5.0
    1.23 mi / 367 ft gain
    This is more of a stroll than a hike, which is nice because you can add it to another hike in the same day if you're in the area. From the dirt parking lot take the trail off to the right. Just stay straight and in about 15 minutes you'll see a huge fire tower (hard to miss). Feel free to climb a...
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  • Mount Washington, Massachusetts

    Mount Frissell and Brace Mountain Loop Trail

    5.08 mi / 807 ft gain
    Mount Frissell and Brace Mountain Loop Trail is a loop trail where you may see beautiful wildflowers located near South Egremont, Massachusetts.
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