Outbound Collective logo

Woodbury, New York

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

Top Hiking Spots in and near Woodbury

  • Briarcliff Manor, New York

    Hike Kate Kennard Trail

    1.8 mi / 140 ft gain
    If 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
  • Vernon Township, New Jersey

    Stairway to Heaven

    4.8
    6.8 mi / 1089 ft gain
    This popular hike starts out on the Appalachian Trail (AT, white blazes). You begin on a boardwalk that crosses over a marsh, then you leave the boardwalk and enter a forested area. At around 1.4 miles, follow a bicycle path, Canal Road, then turn right, cross over a bridge, and take a left throu...
    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
  • 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
  • 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
  • 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
  • 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

    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

    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 ...
    Read more
  • 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 ...
    Read more
  • 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...
    Read more
  • 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 ...
    Read more
  • 89 Van Orden Road, New Jersey

    Hike the Hank's Pond Loop

    7 mi / 500 ft gain
    Hank's Pond loop can be accessed from the south at the corner of Clinton road and Van Orden road or from the north, parking at the lot on Stephens road.  I hiked from the south on this trip.  Follow the wide trail known as Hank's East trail marked with white blazes.  Soon you will reach a trail c...
    Read more
  • Pound Ridge, New York

    Leatherman's Loop

    1.25 mi / 1183 ft gain
    This 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
  • 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...
    Read more
  • Closter, New Jersey

    Hike Alpine White Trail (Stateline Lookout)

    5.0
    5 mi / -520 ft gain
    Starting at about 520 feet, the White path takes you along the Stateline Lookout which is a small stone building overlooking the Hudson River. The initial descent is your average hike through the woods and across a couple of wooden bridges until you reach the Giant Steps. The Giant Steps take you...
    Read more