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Madison, Connecticut

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

Top Chillin Spots in and near Madison

  • 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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  • Patchogue, New York

    Fire Island's Watch Hill

    4.0
    2 mi
    If departing from NYC, catch the early LIRR train from Penn Station (or Atlantic Terminal) towards Patchogue. You may have to transfer at both Jamaica & Babylon, but it's an easy hop across the platform. Trip will take approximately an hour and a half and cost around $15, Off Peak, each way. ...
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  • Washington, Connecticut

    Hike the Mount Tom Tower Trail

    1.3 mi / 337 ft gain
    Starting from the parking lot of Mt. Tom State Park, hop onto the Tower Trail (yellow trail) which leads more into the woods. During winter time, the trail may be slippery, please use your best judgement and always know your limits. Gaining about 300 feet in total elevation in approximately 1 mil...
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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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  • 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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  • 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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  • Stamford, Connecticut

    Hike Cove Island Park Loop Trail

    5.0
    1.1 mi / 3 ft gain
    This trail is accessible year round and features water views of the Long Island Sound with beach access. The trail is a popular spot for walking, biking, fishing, and even bird watching. But if you’re not quite in the mood to get your steps in, you can use the small beach to sit and chat with a f...
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