Thomaston, Connecticut
Looking for the best hiking 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 Hiking Spots in and near Thomaston
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Mount Washington, Massachusetts
Explore Bash Bish Falls
4.21 miOne of my favorite walks to a spectacular falls. The trail is easy to follow and one mile from NY parking lot and 0.5 from the parking lot. The apparent place to swim. There are several very nice, family safe swimmable pools in the creek above and after the falls. There are signs at the top of t...Read more -
Great Barrington, Massachusetts
Mt. Wilcox and Beartown Mountain Trail Loop
5.09.29 mi / 981 ft gainMt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.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 -
East Haddam, Connecticut
Explore Chapman Falls in Devil's Hopyard SP
4.0If 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 set ...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 -
Great Barrington, Massachusetts
Hike Monument Mountain
4.02 mi / 720 ft gainAt 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...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 -
Hampden, Massachusetts
Goat Rock Trail
2.67 mi / 659 ft gainGoat Rock Trail is an out-and-back trail where you may see beautiful wildflowers located near Hampden, Massachusetts.Read more -
Stockbridge, Massachusetts
Laura's Tower and Ice Glen
5.02.4 mi / 676 ft gainYou will park at the end of Park Street in Stockbridge, Massachusetts. From the parking are you will cross a beautiful bridge over the Housatonic River. The trail crosses railroad tracks and immediately begins to climb into the woods. You will reach a split in the trail, a left will take you...Read more -
Cold Spring, New York
Hike the Perkins/Fahnestock/Charcoal Burners Trail Loop
7.5 mi / 800 ft gainThis is one of my favorite hikes in the Clarence Fahnestock State Park. A real mixed bag but mostly very enjoyable. The trail starts at the Charcoal Burners Trailhead Route 301. There is only road side parking on a soft shoulder, both sides of the road. After a short walk into the forest, you re...Read more -
Holyoke, Massachusetts
Whiting Street Reservoir Loop
3.74 mi / 138 ft gainWhiting Street Reservoir Loop is a loop trail that takes you by a lake located near Holyoke, Massachusetts.Read more -
Beacon, New York
Hudson Highlands Overlook Trail
3.29 mi / 1017 ft gainHudson Highlands Overlook Trail is an out-and-back trail that takes you through a nice forest located near Beacon, New York.Read more -
Beacon, New York
Hike Fishkill Ridge
Fishkill Ridge is a strenuous but rewarding hike, and one of the less known areas in the Hudson Valley. The parking area is at the very end of Sunnyside Road in Beacon, along with the information board at the trailhead. The red trail leaves the lot and will take you up to the first peak on the ri...Read more -
Mansfield, Connecticut
Hike Nipmuck Trail
5.08.3 mi / 748 ft gainNipmuck Trail is a 8.3 mile out and back hike that takes you past wildlife located near Mansfield Center, Connecticut.Read more -
Beacon, New York
Hike the Scofield Ridge Loop
7.5 mi / 1850 ft gainThere are some great view points along this route. Start from the Mount Beacon Park trailhead parking area. This leads to the Casino Trail (red markers). The trail climbs steeply to some old ruins of a casino. Most of what remains is only the brick structure housing the mechanics for a trolle...Read more