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Old Saybrook, Connecticut

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

Top Hiking Spots in and near Old Saybrook

  • 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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  • 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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  • 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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  • Montauk, New York

    Climb the Bluffs of Shadmoor State Park

    1.2 mi / 100 ft gain
    I've never actually been into the Shadmoor State Park, but you can climb up and onto the bluffs from the beach easily; well kind of easily.Most of the parking lots along the beach require Hamptons residency tags, so you can't park right next to beach entrances... bummer. We typically park along ...
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  • North Stonington, Connecticut

    Hike Wyassup Lake

    5.0
    2.4 mi / 278 ft gain
    Wyassup Lake is a 2.4 mile out and back hike that takes you past great forest setting located near North Stonington, Connecticut.
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  • Meriden, Connecticut

    Hike the Metacomet, Blue, and Yellow Loop

    5.0
    4.5 mi / 976 ft gain
    Start from the Castle Craig road entrance. Walk until you're greeted by a beautiful reservoir. You'll notice the strange but beautiful Mine Island in the middle of all this. You'll also notice markers for White Trails and Yellow Trails. The White Trail is an easier/wider trail. The Yellow Trail C...
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  • Montauk, New York

    Stroll along the Montauk Point Lighthouse Cliff Walk

    4.5
    1 mi
    The Montauk Point Lighthouse is one of the main attractions of "The End" of Long Island, but I've only ever walked around it on the cliff walk.When you get to the lighthouse, you can park in the parking lot (depending on when you go there may be a $8 fee). Right along the edge overlooking the wa...
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  • Cheshire, Connecticut

    Hike to Roaring Brook Falls

    1.2 mi / 377 ft gain
    Arriving to the falls, parking is residential but don't worry everyone is friendly. Starting off the hike you will walk past a cool pond where you may be able to see some wildlife. Continuing on, you will follow the marked trail where it will take you further into the woods while gaining elevatio...
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  • Berlin, Connecticut

    Hike the Ragged Mountain Memorial Preserve

    4.5
    5.5 mi / 560 ft gain
    Ragged Mountain main loop is approximately 5.5 miles long, and is known for its expansive bare-rock vistas, vertical cliff faces, and scenic views overlooking cliff-side reservoirs and ponds.  The trail is rated moderate, with some flat stretches among the trees, mixed with some uneven rocky foot...
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  • Westerly, Rhode Island

    Grills Preserve

    4.0
    4.27 mi / 351 ft gain
    Grills Preserve is a loop trail that takes you by a lake located near Bradford, Rhode Island.
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  • Southington, Connecticut

    Hike the Crescent Lake & Metacomet Trail Loop

    4.0
    2.4 mi / 269 ft gain
    The hike to view Crescent Lake is peaceful. You can either walk through the woods where you will be blessed with natures finest birds and wildlife or you can take the trail along the lake edge. Both are similar distances and lead to the same hill at the end! Once you get to the top take a left on...
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  • Voluntown, Connecticut

    Hike Pachaug State Forest Trails

    5.0
    3.6 mi / 200 ft gain
    Lawden Brook Trail Loop is a 3.6 mile loop hike that takes you by a lake located near Voluntown, Connecticut.
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  • Hopkinton, Rhode Island

    Hike to Long Pond & Ell Pond

    5.0
    5.7 mi
    Long & Ell Pond is a favorite hike at any time of the year, but it is not for the faint of heart (or small children)! The path immediately becomes more of a rock-scrambling adventure than a hike, but the views are so worth it.  This GPS address will lead you down a dirt road but you should ea...
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  • Mansfield, Connecticut

    Hike Nipmuck Trail

    5.0
    8.3 mi / 748 ft gain
    Nipmuck Trail is a 8.3 mile out and back hike that takes you past wildlife located near Mansfield Center, Connecticut.
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  • Chaplin, Connecticut

    Hike to Diana's Pool

    4.0
    1.3 mi / 45 ft gain
    The drive to Diana's Pool is worth it in an of itself, taking you through the backroads of Eastern Connecticut. To begin the hike just simply enter the woodland path and follow the trail. In order to go under the bridge just simply take the first left in the path and there will be a stream that f...
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