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Pine Plains, New York

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

Top Hiking Spots in and near Pine Plains

  • 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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  • 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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  • 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 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 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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  • 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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  • 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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  • 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

    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...
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  • Beacon, New York

    Hudson Highlands Overlook Trail

    3.29 mi / 1017 ft gain
    Hudson Highlands Overlook Trail is an out-and-back trail that takes you through a nice forest located near Beacon, New York.
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  • 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...
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  • Windham, New York

    Backpack the Catskill's Escarpment Trail

    32.4 mi / 8000 ft gain
    The Escarpment Trail runs the length of the Catskill Escarpment. The Escarpment rises steeply from the valley below forming the northeast corner of the Catskill Mountains. It offers great views toward the Adirondack Mountains to the north and the great Hudson River to the east. The trail is moder...
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  • Carmel Hamlet, New York

    Ninham Mountain Fire Tower

    5.0
    1.23 mi / 367 ft gain
    This is more of a stroll than a hike, which is nice because you can add it to another hike in the same day if you're in the area. From the dirt parking lot take the trail off to the right. Just stay straight and in about 15 minutes you'll see a huge fire tower (hard to miss). Feel free to climb a...
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  • Phoenicia, New York

    Hike Mt. Wittenberg

    4.3
    Looking for a great day hike in the Catskill region of NY? Then you should definitely look into and consider tackling Mt. Wittenberg then. A challenging climb up but a very rewarding summit view.Starting at Woodland Valley Campgrounds visitor registration house (where you can pay for parking for ...
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  • Phoenicia, New York

    Camp at Woodland Valley

    3.0
    If you are looking for a great campground up in the Catskill Mountains of New York then you definitely have to check out Woodland Valley Campgrounds. Located about 2 hours north of New York City, it is the perfect place to go to get off the grid. No service for about 30 minutes in any direction.T...
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  • Beacon, New York

    Explore Long Dock and Dennings Point Parks

    4.0
    Long Dock and Dennings Point are two of the most popular parks in Beacon, that just so happen to be connected by a train track turned trail. Plenty of parking is available at Long Dock, and its a perfect spot to picnic, launch your kayak into the Hudson, or cast your line hoping to reel in the bi...
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