Litchfield, Connecticut
Looking for the best hiking in Litchfield? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Litchfield. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Litchfield
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New Paltz, New York
Hike Mohonk Preserve's Gatehouse to Skytop Tower
5.09 mi / 1268 ft gainBegin at the intersection of Gatehouse Rd and Mohonk Private Rd. There is a small shoulder to park on here. Begin hiking into the preserve along the gatehouse road. There will be signs stating you need a membership or pass to enter. Don't worry about these, there will be a place on the trail ...Read more -
Cornwall-on-Hudson, New York
Hike the Stillman - Bluebird Loop
5.4 mi / 1200 ft gainThis loop hike starts at the northern trailhead of the park where the Stillman Trail begins. The parking area has enough space for only 6 or 7 cars. Start off on a wide maintained carriage road. After about a half mile, the Stillman Trail (yellow markers) breaks of to the left. However, stay ...Read more -
High Falls, New York
Scramble Bonticou Crag and Table Rocks
4.5This is not a hike for the inexperienced. There is a very steep rock scramble that has some dangerous section if you are not aware of your footing and positioning. For those up to the challenge, it is extremely rewarding at the top.To start, each person has to pay $12 to access the Monhonk Preser...Read more -
High Falls, New York
Mohonk Mountain House Labyrinth and Lemon Squeeze Hike
4.5Mohonk Mountain House is a historic resort located just outside the Catskills in the Hudson Valley just 90 miles north of New York City. With 85 miles of winding trails throughout the Mohonk Preserve, you'll have endless hiking options upon your arrival.Parking at the Gatehouse is limited, so be ...Read more -
Philipstown, New York
Hike the Osborn Loop
7.6 mi / 850 ft gainThe Osborn Loop trail itself is not a loop. It connects to a 2.5 mile section of the Appalachian Trail. Hiking these together creates the loop. Start at the trail head for the Appalachian Trail on South Mountain Pass Road. There is parking for two or three cars. Walk up the road a short dist...Read more