Outbound Collective logo

Windham, New York

Looking for the best hiking in Windham? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Windham. The detailed guides, photos, and reviews are all submitted by the Outbound community.

Top Hiking Spots in and near Windham

  • 3197 U.S. 44, New York

    Hike to Sky Top via the Undercliff Road

    7.3 mi / 900 ft gain
    Starting 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
  • East Nassau, New York

    Kinderhook Creek

    5.0
    1.62 mi / 308 ft gain
    Kinderhook Creek is a loop trail that takes you by a river located near Stephentown, New York.
    Read more
  • Gardiner, New York

    Gertrude's Nose

    4.9
    6.97 mi / 919 ft gain
    It 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

    Lake Minnewaska Loop Trail

    2.01 mi / 348 ft gain
    Lake Minnewaska Loop Trail is a loop trail where you may see beautiful wildflowers located near Kerhonkson, New York.
    Read more
  • Gardiner, New York

    Hike the Millbrook Mountain/Gertrude Nose loop

    9 mi / 1700 ft gain
    This 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
  • Mount Washington, Massachusetts

    Explore Bash Bish Falls

    4.2
    1 mi
    One 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
  • Mount Washington, Massachusetts

    Guilder Pond and Mount Washington Lookout Trail

    3.92 mi / 909 ft gain
    Guilder Pond and Mount Washington Lookout Trail is a loop trail that takes you by the lake located near Copake Falls, New York.
    Read more
  • Mount Washington, Massachusetts

    Mount Frissell and Brace Mountain Loop Trail

    5.08 mi / 807 ft gain
    Mount Frissell and Brace Mountain Loop Trail is a loop trail where you may see beautiful wildflowers located near South Egremont, Massachusetts.
    Read more
  • Cragsmoor, New York

    Sam's Point, Ice Cave Trail, Verkeerderkill Falls

    4.9
    6.99 mi / 1063 ft gain
    Located in Sam's Point Preserve, this hike has three major attractions – panoramic views from Sam's Point, mysterious and chilly Ice Caves, and a knee-weakening perch atop Verkeerderkill Falls. Pay attention to seasonal conditions before making this trip. Spring and early summer are best for see...
    Read more
  • Cragsmoor, New York

    Sam's Point Overlook to Ice Cave Trail

    3.47 mi / 584 ft gain
    Sam's Point Overlook to Ice Cave Trail is an out-and-back trail with scenic views near Lake Maratanza located near Ellenville, New York. This trail is dog friendly on-leash. 
    Read more
  • Sheffield, Massachusetts

    Hike to Race Brook Falls

    4.0
    3.4 mi / 1174 ft gain
    Hiking 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
  • 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
  • Salisbury, Connecticut

    Bear Mountain Loop

    4.5
    6.05 mi / 1516 ft gain
    At 2,316 feet, Bear Mountain is the highest peak in Connecticut. The peak is about a half-mile south of the Massachusetts state line on the Appalachian Trail. The views are great. On a clear day you can see some of the peaks in southern New Hampshire. The remnants of a stone tower are on the summ...
    Read more
  • Great Barrington, Massachusetts

    Hike Monument Mountain

    4.0
    2 mi / 720 ft gain
    At 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
  • Stockbridge, Massachusetts

    Laura's Tower and Ice Glen

    5.0
    2.4 mi / 676 ft gain
    You 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
  • Great Barrington, Massachusetts

    Mt. Wilcox and Beartown Mountain Trail Loop

    5.0
    9.29 mi / 981 ft gain
    Mt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.
    Read more