New Windsor, New York

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

Top Hiking Spots in and near New Windsor

  • 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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  • Bridgeport, Connecticut

    Stroll around Fayerweather Island

    0.5 mi
    Parking is at the end of Barnum Road in the Seaside Park.  Though the lighthouse grounds are accessible the tower itself is not open to the public.  To access the island you must walk across the breakwater.  Please use caution as it is uneven footing and at times can be slippery.  From the isla...
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  • Dingmans Ferry, Pennsylvania

    Explore Dingmans Falls

    3.8
    0.4 mi
    The waterfall is about 0.2 miles into the hike. I would recommend going to the very top of the biggest waterfall towards the end of the hike, there are steps leading up to it! There's also a hidden water hole at the very top of the waterfall about 0.2 miles up stream, I saw people in it during th...
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  • New York, New York

    Jacqueline Kennedy Onassis Reservoir Running Path

    5.0
    1.68 mi / 69 ft gain
    Jacqueline Kennedy Onassis Reservoir Running Path is a loop trail that takes you by a lake located near New York City, New York.
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  • Barryville, New York

    Camp at Kittatinny Campground

    This campground is perfect for a group of friends that want to spend a couple days outdoors camping!With 350 campsites, there are many different types of sites available: from sites with electricity to sites 3 miles from the main camp. Decide how intense (or not intense) you and your group want ...
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  • New York, New York

    Northwest Central Park Loop

    3.63 mi / 164 ft gain
    The Northwest Central Park Loop in New York City offers a scenic, family-friendly experience through some of the park’s quieter sections. The loop features well-maintained paths, stunning views of the surrounding nature, and landmarks like the Reservoir. It’s perfect for walking, jogging, or ca...
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  • 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.
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  • Salisbury, Connecticut

    Bear Mountain Loop

    4.7
    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...
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  • Dingmans Ferry, Pennsylvania

    Hornbecks Creek Waterfall

    4.3
    2.16 mi / 226 ft gain
    Follow the Hornbeck Creek Trail for approximately 1 mile, until the trail comes to an end and opens up into the waterfall and large pool beneath it. There is a rope swing to the left of the falls for swimming. Driving Directions: From 209, enter into the Delaware Water Gap and in between the 10...
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  • Dingmans Ferry, Pennsylvania

    George W Child's Park

    4.0
    1.12 mi / 108 ft gain
    Once parked, enter the trailhead and follow the trail down Dingmans Creek to the first set of falls. Try taking pictures from off the trail to the right of these falls. Continue on to the second waterfall and again step off the trail to take pictures from the right side of the waterfall, if you d...
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  • Elka Park, New York

    Layman's Monument and Kaaterskill Falls

    3.05 mi / 892 ft gain
    Layman's Monument and Kaaterskill Falls is an out-and-back trail that takes you to one of New York's tallest waterfalls at 231 feet and to the historical monument for Frank D. Layman, who passed away in 1990 while fighting a forest fire. This trail is located near Haines Falls, New York.
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  • Greene County, United States

    Hike to Newman's Ledge

    4 mi / 584 ft gain
    Located in the beautiful Catskill Mountains, this is an outdoors-mans(and woman's) dream spot! Although this hike is accessible year round, if you decide to go during the summer you should expect crowds. Luckily, there are so many different trails and activities that it won't even matter. North-S...
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  • Palenville, New York

    Kaaterskill Falls via Laurel House

    4.5
    1.67 mi / 360.89 ft gain
    This short hike is one of the most popular in the Catskills — and for good reason. From the Laurel House Road Trailhead, it’s less than a mile round trip to reach Kaaterskill Falls, New York’s tallest two-tiered waterfall, with a dramatic 260-foot drop into a rocky amphitheater. The trail itse...
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  • Tannersville, New York

    Kaaterskill Rail Trail + Kaaterskill Falls

    5.0
    3.61 mi / 246 ft gain
    The Kaaterskill Rail Trail begins near Haines Falls, New York heading toward North and South Lake. The trail is set in a gorgeous forest, and is used for hiking, trail running, and birding trips. The trail provides exceptional views of the surrounding mountains, valleys, forests, and towns. 
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  • Dingmans Ferry, Pennsylvania

    Hike to Indian Ladder Falls Along Hornbecks Creek

    3.5
    2 mi / 400 ft gain
    For some time, the trail was eroded above the first falls on Hornbecks Creek, not allowing hikers to access the creek's upper falls if they were coming upstream from Route 209. I am writing this in June 2017 and that is no longer the case! You can hike from Rt. 209 all the way up the creek to Eme...
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