Bear Mountain, New York

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

Top Hiking Spots in and near Bear Mountain

  • Jefferson, New Jersey

    Thru Hike the Four Birds Trail

    19 mi / 1200 ft gain
    The Four Birds Trail is about 19 miles long and is a great thru hike or can be done in sections as out and back hikes or part of loop hikes with other trails.  Starting from the north, the trail ascends gradually over easy terrain until you reach a cliff ridge.  There are several good view points...
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  • Rye, New York

    Hike the Marshlands Conservancy Loop

    4.0
    1.55 mi / 125 ft gain
    Located along the Long Island Sound, this 147-acre conservancy is home to a plethora of different birds, including marsh wrens, seaside sparrows, and American woodcocks. The conservancy has 3 miles of trails, all easy to navigate. Starting out from the visitor's center, take the trail to the rig...
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  • Englewood Cliffs, New Jersey

    Hike the Dyckman Hill/Huyler's Landing Loop

    9 mi / 980 ft gain
    There is two ways to access this loop hike.  The first is from the Englewood Picnic area just off Exit 1 from the Palisades Interstate Parkway.  Parking here requires a fee of $5 May through September. The second is to drive past the Englewood Picnic area turnoff on Henry Hudson Drive and continu...
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  • New Paltz, New York

    Hike Mohonk Preserve's Gatehouse to Skytop Tower

    5.0
    9 mi / 1268 ft gain
    Begin 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 ...
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  • New Fairfield, Connecticut

    Hike Squantz Pond Trail

    2.2 mi / 321 ft gain
    The hike is rated as moderate and is accessible all year round. While it’s accessible during all seasons, the sights of the leaves changing colors in the autumn makes it an exceptionally beautiful time to do this hike. You’ll definitely want to snap some photos along the way of the foliage reflec...
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  • 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...
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  • Englewood Cliffs, New Jersey

    Hike the Dyckman Hill/Carpenter's Grove Loop

    4.0
    4 mi / 400 ft gain
    This loop hike can be started from several different places.  I chose to start from Allison Park which overlooks the Hudson River in Englewood Cliffs, NJ.  From the parking area, walk out to the entrance road and travel south to Saint Peter's College.  The Long Path Trail, which you join from All...
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  • 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. 
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  • 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...
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  • Gardiner, New York

    Hike The Millbrook Mountain Ridge Trail

    5.0
    7 mi / 1400 ft gain
    Want 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 ...
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  • Gardiner, New York

    Hike the Dickie Barre, Peters Kill and Awosting Falls Loop

    3.0
    7.8 mi
    This 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 ...
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  • Gardiner, New York

    Hike the Overcliff - Undercliff Road Loop

    5.3 mi / 350 ft gain
    From 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...
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  • Gardiner, New York

    Millbrook Mountain & Gertrude Nose loop

    8.77 mi / 1253 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...
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  • 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.
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  • 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...
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  • Stamford, Connecticut

    Hike Cove Island Park Loop Trail

    5.0
    1.1 mi / 3 ft gain
    This trail is accessible year round and features water views of the Long Island Sound with beach access. The trail is a popular spot for walking, biking, fishing, and even bird watching. But if you’re not quite in the mood to get your steps in, you can use the small beach to sit and chat with a f...
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