Old Saybrook, Connecticut

Looking for the best chillin 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 Chillin Spots in and near Old Saybrook

  • East Haddam, Connecticut

    Explore Chapman Falls in Devil's Hopyard SP

    4.0
    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 set ...
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  • Shelter Island, New York

    Hike through the Mashomack Nature Preserve

    10 mi
    Just a short ferry ride from the Hamptons, South Ferry Road is exactly where it sounds; very close to the South Ferry of Shelter Island. The parking lot of Mashomack Preserve is marked by a large sign. When you walk in, you'll see a large nature center. Sign in at a clipboard at the table out fro...
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  • Middlesex County, Connecticut

    Hike to Glen Falls

    5.0
    0.75 mi
    Accessing Glen Falls may be a little tricky at first. Parking will be very minimal, you will park on Grist Mill Ln. Hop onto the road and you will see the trail map on the left side. The adventure begins when you cross the street and go through the gate with the yellow blaze symbol. Keep followin...
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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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  • Meriden, Connecticut

    Higby Mountain Trail

    2.11 mi / 486 ft gain
    The popular route for this hike is to park your car at the base of the trail which is located right before merging onto 91-S in Middlefield, CT. The parking lot does seem to get crowded mid-day, especially if the weather is nice!  The beginning of the hike is mostly flatter land and an incline w...
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  • 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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  • 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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  • 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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  • 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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  • Westerly, Rhode Island

    Watch the Sunset over Misquamicut Beach

    5.0
    Misquamicut is one of Rhode Island’s most popular beach locations during the day. As the evening approaches most beach goers pack up, tired from a day of playing in the waves and lounging on the beach’s beautiful sand. It’s during this time, when the crowds disperse and the day begins to turn to ...
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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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  • 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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  • Manchester, Connecticut

    Explore Wickham Park

    5.0
    Wickham Park Is open the first weekend in April and closes the last weekend in October. Entrances fees are $5 Monday-Friday and $7 Saturday-Sunday. The park is known for its 250 acres of  open fields, wildflowers, gardens, ponds and nature center. There is no where else can you go have a picnic w...
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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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  • Charlestown, Rhode Island

    Watch the Sunrise at East Beach, RI

    Walking over the dunes in the dark you can hear the waves breaking on shore from the parking lot. Wet suited up, camera in hand, make your way over the dunes and down to the water. East Beach is a sandy beach and with the right swell size and direction you'll get some sizable shore break to play ...
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