Washington, Connecticut
Looking for the best hiking in Washington? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Washington. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Washington
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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 -
Great Barrington, Massachusetts
Hike Monument Mountain
4.52 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 -
New Windsor, New York
Jessup/West Ridge Loop via the Sweet Clover Trail
9.17 mi / 1916 ft gainSchunnemunk Mountain State Park is one of my favorite parks. It offers many trails and possibilities for different loops. The attraction of Schunnemunk Mountain is the long double ridges running parallel to each other and amazing views in all directions. This hike starts at the Taylor Road par...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 -
Briarcliff Manor, New York
Hike Kate Kennard Trail
1.8 mi / 140 ft gainIf you’re in the town of Briarcliff and looking for an easy local trail to try out, Kate Kennard Trail is good for getting in a quick run or walk. It’s a straight line path the whole way. You’ll know you’ve reached the end of the path when you see a sign that marks the beginning of a road leading...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 -
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 -
Pleasantville, New York
Swan Lake Loop
5.01.37 mi / 85 ft gainSwan Lake Loop is a loop trail that takes you by a lake located near Hawthorne, New York.Read more -
3197 U.S. 44, New York
Hike to Sky Top via the Undercliff Road
7.3 mi / 900 ft gainStarting from the East Trapps parking area ascend the East Trapps connector trail marked with yellow blazes. You can also park at the Mohonk Preserve visitor center where you can purchase your access pass ($15 per person) and pick up a free map of the presere trails and carriage roads. The conn...Read more -
Hudson, New York
High Falls Conservation Area Loop
1.41 mi / 194 ft gainHigh Falls Conservation Area Loop is a loop trail that takes you by a waterfall located near Philmont, New York.Read more -
Gardiner, New York
Hike The Millbrook Mountain Ridge Trail
5.07 mi / 1400 ft gainWant to walk on the edge? visit Millbrook Mountain in the Catskills of NY. This loops hike follows the mountains ridge line most of the way to the summit with multiple viewpoints and cliff ledges to walk out on. This hike is recommended those in the area.Park at West Trapps Parking Lot and head ...Read more -
Gardiner, New York
Hike the Dickie Barre, Peters Kill and Awosting Falls Loop
3.07.8 miThis loop hike takes you to Awosting Falls (65 ft.), as well as to great valley views along the ridge of Dickie Barre, and across Peters Kill, on the way.Start out on West Trapps Connector Trail (yellow blazes) at the east end of the West Trapps parking lot (get their early because the lot will ...Read more -
Gardiner, New York
Hike the Overcliff - Undercliff Road Loop
5.3 mi / 350 ft gainFrom the West Trapps parking lot ($15 for hikers), walk to the end of the parking lot and past a large kiosk. The trail connects the parking lot to the Overcliff Road/Undercliff Road junction. The loop can be done in either direction. I turned left on the Overcliff Road. This takes you behind...Read more -
Gardiner, New York
Gertrude's Nose
4.96.97 mi / 919 ft gainIt would be impossible to see all of Minnewaska’s beautiful spots in one day. Gertrude's Nose is, in my opinion, the best view in the entire park. Round trip, the hike is approximately 5 hours, and is a 7.5 mile trip. To get to the trailhead: Drive to the Minnewaska State Park entrance, pass the...Read more -
Gardiner, New York
Millbrook Mountain & Gertrude Nose loop
8.77 mi / 1253 ft gainThis great loop hike starts from the upper parking lot of Lake Minnewaska State Park. Walk towards Lake Minnewaska and once on that carriage road, turn left and follow the road to the to the opposite end of the lake. Along the way are great view points of the lake and several picnic areas for day...Read more