Philipstown, New York

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

Top Hiking Spots in and near Philipstown

  • Sharon, Connecticut

    Hike the Pine Knob Loop, Housatonic Meadows SP

    5.0
    2.5 mi / 770 ft gain
    The Pine Knob loop is a 2.5 mile loop trail that takes you through beautiful thick  woods filled with vistas, wild flowers and tons of wild life.  You will start your adventure at the Pine Knob Trail head where you will be able to a Connecticut Appalachian trail guide. Pine Knob is a blue blaze ...
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  • New York, New York

    High Line

    4.8
    1.47 mi / 26 ft gain
    Built on a historic freight rail line and perched above the streets of Manhattan’s West Side, the High Line is a public park that features a green-lined walkway. Park hours depend on the season, although it never opens before 7am, so best to go for sunset. Although you may have some company on wa...
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  • Sandyston, New Jersey

    Explore the Sussex County Sunflower Maze

    5.0
    3 mi
    I stumbled upon the Sunflower Maze by accident when I was driving through NJ and was quickly distracted by the enormous yellow flowers. So of course, I had to check it out! It opens at 9AM and last admission is at 6PM. The maze is only open from around August to October for the flower bloom. 3...
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  • Sandyston, New Jersey

    Hike the AT to Culvers Lookout Tower

    3.2 mi
    Start your journey in Stokes State Forest at the Culver Gap Parking Lot, located at 41.180239, -74.787954. From the parking lot, jump on over to the Appalachian Trail and hike Northbound. You know you're headed the right way if you are going away from the small town and cross over Sunrise Mountai...
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  • New York, New York

    Brooklyn Bridge Walk

    5.0
    2.4 mi / 26 ft gain
    Brooklyn Bridge Walk is an out-and-back trail that takes you by a river located near New York City, New York.
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  • Brooklyn, New York

    Brooklyn Bridge Walk via Brooklyn

    4.7
    1.12 mi / 0 ft gain
    Walking the Brooklyn Bridge from the Brooklyn side is a rewarding experience that blends history, architecture, and stunning views of New York City. Start your journey at the pedestrian entrance near Cadman Plaza, which is easily accessible by subway (Court Street or High Street stations). The br...
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  • Milford, Pennsylvania

    Hike to Cliff Park Ridge

    5.0
    6.4 mi / 700 ft gain
    This 6.4 mile out-and-back trail (2.7 miles each way) is an excellent trail for those looking to spend an early morning or afternoon outside without the strenuousness of all-out mountain hiking. Throughout the entire hike, there is only 700 ft. of elevation gain. Don't let this turn you away if y...
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  • Milford, Pennsylvania

    Raymondskill Falls

    4.0
    0.41 mi / 92 ft gain
    This waterfall is just a short walk away from the main parking lot. Just a .30 mile hike will take you to a gorgeous three-tiered waterfall. There are platforms providing viewing areas to the falls. Raymondskill Falls is located in the northern portion of the Delaware National Water Gap Recreat...
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  • Woodstock, New York

    Overlook Mountain Trail

    4.53 mi / 1348 ft gain
    It is important to know that parking for the head of this trail is great, located on Meads Mountain Rd in Woodstock NY. The trail is clearly a gravel road marked by Red trail markers, on a gradual inline up to the Hotel first, at the 2 mile mark, and then the Fire Tower is 0.5 miles further down...
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  • Brooklyn, New York

    Brooklyn Botanical Gardens

    5.0
    1.34 mi / 75 ft gain
    Brooklyn Botanical Gardens is a loop trail that takes you by a lake located near New York City, New York.
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  • Brooklyn, New York

    Prospect Park Loop

    4.7
    3.65 mi / 223 ft gain
    There are multiple places to enter Prospect Park. If you're looking for the main entrance to Prospect Park, it faces the stunning Soldiers' and Sailors' Arch in Grand Army Plaza. It is adjacent to the Brooklyn Botanical Garden, the flagship Brooklyn Public Library, and the Brooklyn Museum. As you...
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  • 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...
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  • Canaan, Connecticut

    Explore Great Falls

    3.0
    0.5 mi
    Stumbled upon Great Falls in the Falls Village section of Canaan, CT. The stunning 50ft waterfall doesn't disappoint. very easy hike from parking lot, you must cross the river in order to get close for bottom view. Hop on top of turtle rock and relax as the waterfall tumbles in the distance.
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