Middlebury, Connecticut
Looking for the best hiking in Middlebury? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Middlebury. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Middlebury
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Kent, Connecticut
Hike the Ridge Loop Trail, Macedonia Brook SP
3.0For a quick weekend trip from Newport, RI, Macedonia Brook State Park had a lot to offer for its size. In three or four hours, with lunch, you can hike the 6.4 mile ridge trail and get some fresh air without having to hike on too busy of trails. The elevation gain is only around 700 ft, however, ...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 -
Simsbury, Connecticut
Hike to the Heublein Tower on Talcott Mountain
4.32.54 mi / 404 ft gainThe 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 ...Read more -
Dover Plains, New York
Hike Dover's Stone Church
4.5Dover Stone Church has been a beautiful and popular destination in the Hudson Valley for some time, and recently the park purchased a new parcel of land and added three trails through the nearby woods. But the gem of the park is, and always will be, the impressive cave with the creek and waterfal...Read more -
Middlesex County, Connecticut
Hike to Glen Falls
5.00.75 miAccessing 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...Read more -
Glastonbury, Connecticut
Hike the Cotton Hollow Nature Preserve
5.03 miThere 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 ...Read more -
Pound Ridge, New York
Leatherman's Loop
1.25 mi / 1183 ft gainThis loop trail is moderately rated and reaches a total elevation gain of approximately 1,183 feet. It’s located in the Ward Pound Ridge Reservation, which spans roughly 4,315 acres. It is Westchester County’s largest park and includes roughly 35 plus miles of hiking trails to explore. The Ward...Read more -
Carmel Hamlet, New York
Ninham Mountain Fire Tower
5.01.23 mi / 367 ft gainThis is more of a stroll than a hike, which is nice because you can add it to another hike in the same day if you're in the area. From the dirt parking lot take the trail off to the right. Just stay straight and in about 15 minutes you'll see a huge fire tower (hard to miss). Feel free to climb a...Read more -
Granby, Connecticut
Enders Falls
4.00.5 mi / 118 ft gainEnders 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...Read more -
Canaan, Connecticut
Explore Great Falls
3.00.5 miStumbled upon Great Falls in the Falls Village section of Canaan, CT. The stunning 50ft waterfall doesn't disappoint. very easy hike from parking lot, you must cross the river in order to get close for bottom view. Hop on top of turtle rock and relax as the waterfall tumbles in the distance.Read more -
Kent, New York
King's Chamber and Moose Hill Loop
3.14 mi / 499 ft gainKing's Chamber and Moose Hill Loop is a loop trail that takes you by a lake located near Carmel, New York.Read more -
Norfolk, Connecticut
Campbell Falls
4.00.99 mi / 161 ft gainCampbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....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 -
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 -
Hopewell Junction, New York
Lake Canopus Viewpoint
4.02.07 mi / 148 ft gainIts a great place to explore as it has a beautiful calm lake especially in the fall, the reflection of the water and the awesome colors are unbelievable. Its a short hike but you certainly could go further up. Parking is free by the road, hike towards the lake about a mile or so. The sound of bi...Read more -
Hopewell Junction, New York
Beaver Pond via Appalachian Trail
5.03 mi / 400 ft gainBeaver Pond is a small body of water created by a dam that was constructed during the days of iron ore mining in the area. The pond is crystal clear and has a wonderful tree line right on the water. The best time to visit here is early morning in the fall. With the leaves changing color they m...Read more