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Canaan, Connecticut

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

Top Hiking Spots in and near Canaan

  • Glastonbury, Connecticut

    Hike the Cotton Hollow Nature Preserve

    5.0
    3 mi
    There are two parking locations for Cotton Hollow, the location tagged in the directions is the shortest hike to the old gun powder mill. Suggestions when it comes to exploring the preserve are to stay on the trails, know your limits, and enjoy! There are swimming holes along the river, but swim ...
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  • Hampden, Massachusetts

    Goat Rock Trail

    2.67 mi / 659 ft gain
    Goat Rock Trail is an out-and-back trail where you may see beautiful wildflowers located near Hampden, Massachusetts.
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  • Kent, New York

    King's Chamber and Moose Hill Loop

    3.14 mi / 499 ft gain
    King's Chamber and Moose Hill Loop is a loop trail that takes you by a lake located near Carmel, New York.
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  • Beacon, New York

    Hudson Highlands Overlook Trail

    3.29 mi / 1017 ft gain
    Hudson Highlands Overlook Trail is an out-and-back trail that takes you through a nice forest located near Beacon, New York.
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  • Hamden, Connecticut

    Hike the Tower Trail to the Blue Trail at Sleeping Giant SP

    5.0
    3 mi / 518 ft gain
    Sleeping Giant State Park is a place very close to my heart. I spent 4 years right across the street at Quinnipiac University and have hiked “The Giant” more times then I can count and at all different hours. There are a few different trails you can explore but my favorite one is up to the cliffs...
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  • Hamden, Connecticut

    Hike the Mill River Trail to the Blue Trail at Sleeping Giant SP

    5.0
    3 mi / 518 ft gain
    Since I was a child, I’ve always enjoyed hiking the Giant. As Connecticut parks go, this terrain is some of the most challenging (and unfortunately, the most dangerous) in the state. The actual ridge is approximately 2.75 miles long by 1.75 miles wide, and offers approximately 24 miles of hiking ...
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  • Beacon, New York

    Hike Fishkill Ridge

    Fishkill Ridge is a strenuous but rewarding hike, and one of the less known areas in the Hudson Valley. The parking area is at the very end of Sunnyside Road in Beacon, along with the information board at the trailhead. The red trail leaves the lot and will take you up to the first peak on the ri...
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  • Hamden, Connecticut

    Boulder & Free Climb off the Blue Trail In Sleeping Giant SP

    Sleeping Giant State Park does not just have great hiking, it also has great climbing and bouldering. Pick up the blue trail starting at the backside of the visitor center. This trail climbs pretty steadily but take note that as you hike up the cliff below you is a great spot to checkout for boul...
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  • Middletown, Connecticut

    Explore Wadsworth Falls

    5.0
    0.25 mi
    When it comes to exploring Wadsworth Falls its ease of access couldn't be better. As soon as you pull into the parking lot you hear the falls roaring. Take the quick walk to see the picturesque scenery.Facts about Wadsworth Falls:Height: 25ft tall and doubled in width Rock: Hampden Basalt -the ro...
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  • Ridgefield, Connecticut

    Hike the Hemlock Hills & Pine Mountain Loop

    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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  • Hopewell Junction, New York

    Beaver Pond via Appalachian Trail

    5.0
    3 mi / 400 ft gain
    Beaver Pond is a small body of water created by a dam that was constructed during the days of iron ore mining in the area.  The pond is crystal clear and has a wonderful tree line right on the water.  The best time to visit here is early morning in the fall.  With the leaves changing color they m...
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  • Hopewell Junction, New York

    Lake Canopus Viewpoint

    4.0
    2.07 mi / 148 ft gain
    Its a great place to explore as it has a beautiful calm lake especially in the fall, the reflection of the water and the awesome colors are unbelievable. Its a short hike but you certainly could go further up. Parking is free by the road, hike towards the lake about a mile or so. The sound of bi...
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  • Windham, New York

    Backpack the Catskill's Escarpment Trail

    32.4 mi / 8000 ft gain
    The Escarpment Trail runs the length of the Catskill Escarpment. The Escarpment rises steeply from the valley below forming the northeast corner of the Catskill Mountains. It offers great views toward the Adirondack Mountains to the north and the great Hudson River to the east. The trail is moder...
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  • Deerfield, Massachusetts

    South Sugarloaf Trail

    1.48 mi / 404 ft gain
    South Sugarloaf Trail is a loop trail that takes you by a river located near South Deerfield, Massachusetts.
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  • 3197 U.S. 44, New York

    Hike to Sky Top via the Undercliff Road

    7.3 mi / 900 ft gain
    Starting from the East Trapps parking area ascend the East Trapps connector trail marked with yellow blazes.  You can also park at the Mohonk Preserve visitor center where you can purchase your access pass ($15 per person) and pick up a free map of the presere trails and carriage roads.  The conn...
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  • Cold Spring, New York

    Hike the Perkins/Fahnestock/Charcoal Burners Trail Loop

    7.5 mi / 800 ft gain
    This is one of my favorite hikes in the Clarence Fahnestock State Park. A real mixed bag but mostly very enjoyable. The trail starts at the Charcoal Burners Trailhead Route 301. There is only road side parking on a soft shoulder, both sides of the road.  After a short walk into the forest, you re...
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