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Westbrook, Connecticut

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

Top Chillin Spots in and near Westbrook

  • Simsbury, Connecticut

    Hike to the Heublein Tower on Talcott Mountain

    4.3
    2.54 mi / 404 ft gain
    The Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...
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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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  • Charlestown, Rhode Island

    Visit the Frosty Drew Observatory

    The Frosty Drew Observatory is located near the tip of southern Rhode Island, which means apart from summer this is a very quiet beach town. The isolation from major urban areas provides the perfect conditions for star-gazing. The building itself is located on a large plot of land dedicated to na...
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  • Charlestown, Rhode Island

    Car Camp at Charlestown Breachway Campground

    Rhode Island is nicknamed the Ocean State for a reason, and camping by the coast is something absolutely necessary while in New England. During the summer and early fall, Charlestown, RI, as well as the surrounding beach towns, come alive with tourists from all over the globe. The Breachway Campg...
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  • New Shoreham, Rhode Island

    Walk to North Lighthouse

    1 mi / 0 ft gain
    In order to reach the Lighthouse you must walk along the trail that begins at the end of Corn Neck Rd. This walk is along the beach and then veers off to the left once you get closer to the light house (the seventh picture shows the start of the walk). It's only a half mile to the light house, bu...
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  • New Shoreham, Rhode Island

    Explore Block Island

    5.0
    Block Island, a small island off the coast of the Rhode Island mainland, is well-known as a local summer playland. Tourists typically go to the quaint New England island in the summer months for the biking, hiking, sailing, kayaking, fishing and 17 miles of beaches.Although you can bring a car o...
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  • New Shoreham, Rhode Island

    Explore Block Island on Mopeds

    Block Island offers beautiful beaches, lighthouses, cliffs, and harbors - but what's the best way to see them all? Mopeds of course! We went through Island Moped & Bike but there are other options if you want to shop around. We chose them because they had a special rate for an afternoon/eveni...
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  • New Shoreham, Rhode Island

    Explore the Mohegan Bluffs

    If you make the ferry ride to Block Island the bluffs are a must-see. From the town where the ferry ports, it's about two miles to get there. If you don't travel with your car you can always walk there via the road, bike ride, or rent a moped! There is no fee to use the beach and it can be access...
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  • New Shoreham, Rhode Island

    Explore the South East Lighthouse

    If you're visiting the Mohegan Bluffs, you should take the extra time to see the Lighthouse next to them. There's a beautiful overlook looking out onto the Atlantic and a bench to relax in the grassy hill. It's free to walk around the grounds and it's only about 2 miles from the town the ferry po...
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  • Granby, Connecticut

    Hiking Enders Falls

    4.0
    Enders State Forest sprawls over approximately 2000 acres, and is found within the towns of Granby and Barkhamsted in Connecticut.  Enders has a good sized parking lot directly on Route 219.  From the junction of Route 219 and Route 20, visitors will proceed west on Route 219 for 1.2 miles and tu...
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