Thomaston, Connecticut
Looking for the best chillin in Thomaston? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Thomaston. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Chillin Spots in and near Thomaston
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Salisbury, Connecticut
Explore Riga Falls
The best part of the adventure is finding this hidden gem also known as Riga Falls. Riga Falls is actually one of Connecticut's lesser known waterfalls, but arguably the most scenic. A helpful hint is that the waterfall lies beside dirt road, keep your ears open! I've already said too much, happy...Read more -
Glastonbury, Connecticut
Blackledge Falls
4.01.46 mi / 207 ft gainAlthough 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...Read more -
Sheffield, Massachusetts
Race Brook Falls
4.02.47 mi / 1145 ft gainHiking along the Appalachian trail I made a detour in Mt Everett State reservation. About a 2.5 mile detour lead me down to a beautiful 100ft waterfall called Race Brook falls. The waterfall felt made me feel like i was in the tropical jungle in Hawaii. Adding to the beauty of the waterfall were ...Read more -
Bridgeport, Connecticut
Stroll around Fayerweather Island
0.5 miParking is at the end of Barnum Road in the Seaside Park. Though the lighthouse grounds are accessible the tower itself is not open to the public. To access the island you must walk across the breakwater. Please use caution as it is uneven footing and at times can be slippery. From the isla...Read more -
Mount Washington, Massachusetts
Bash Bish Falls
4.30.75 mi / 295 ft gainBash Bish Falls is a spectacular 60-foot waterfall located on the Massachusetts-New York border in the southern Berkshires. This popular destination offers easy hiking access and stunning natural beauty, making it perfect for families and casual hikers. Parking Options Massachusetts Side: 0...Read more -
East Haddam, Connecticut
Chapman Falls
4.00.55 mi / 49 ft gainIf 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 se...Read more -
Philipstown, New York
Indian Brook Falls (CLOSED)
2.80.59 mi / 157 ft gainIndian Brook Falls is CLOSED as of 2022. Learn more at HighlandsCurrent.org. Take a short simple walk to a beautiful waterfall near the Constitution Marsh and Audubon Center. This waterfall is great spot for the whole family to take in its beauty. This is about as short a walk and as little eff...Read more -
Beacon, New York
Explore Long Dock and Dennings Point Parks
4.0Long Dock and Dennings Point are two of the most popular parks in Beacon, that just so happen to be connected by a train track turned trail. Plenty of parking is available at Long Dock, and its a perfect spot to picnic, launch your kayak into the Hudson, or cast your line hoping to reel in the bi...Read more -
Stamford, Connecticut
Hike Cove Island Park Loop Trail
5.01.1 mi / 3 ft gainThis 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...Read more -
Chaplin, Connecticut
Hike to Diana's Pool
4.01.3 mi / 45 ft gainThe 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...Read more