Old Chatham, New York

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

Top Hiking Spots in and near Old Chatham

  • 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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  • North Adams, Massachusetts

    The Cascades Trail

    4.3
    1.97 mi / 315 ft gain
    The Cascades Trail is an out-and-back trail that takes you by a waterfall located near North Adams, Massachusetts.
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  • Niskayuna, New York

    Lisha Kill Preserve Loop

    4.5
    2.22 mi / 200 ft gain
    This 2.2 mile loop trail is lightly trafficked and great for all skill levels. Starting out the trail register, you will see signs from The Nature Conservancy which manages the preserve. Descending down a hill with lots of exposed tree roots, you will then cross over the meandering Lisha Kill and...
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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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  • 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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  • Tannersville, New York

    North Mountain

    4.7
    6.16 mi / 1060 ft gain
    Have you ever wanted to feel as if you were hiking two different locations at once? If so, then North Mountain is definitely somewhere to check out. Take the birch tree forests around Aspen, CO and pair it with the spruces/pines of the Adirondacks and you'll have this route in the Catskills. Par...
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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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  • 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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  • Savoy, Massachusetts

    Tannery Falls Loop

    0.54 mi / 135 ft gain
    The hike to Tannery Falls may be a little confusing, I'll clear it up for you before you even go there! To get to The falls you will travel down a dirt road that isn't very well maintained during the winter. As you keep driving down the dirt road you will notice a pond , which means you are almos...
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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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  • 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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  • Norfolk, Connecticut

    Campbell Falls

    4.0
    0.99 mi / 161 ft gain
    Campbell Falls, one of the most beautiful parks in CT. Don't let the size of the park fool you, that's what adds to the beauty. With it's strong pine and fresh flower scented woods you slowly forget that you're even in Connecticut. The trails aren't labeled the greatest but still can be made out....
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  • Sandisfield, Massachusetts

    Buck River Swimming Hole

    4.0
    0.3 mi / 250 ft gain
    This swimming hole is 7-feet deep. At the top of the swimming hole is a 12-foot waterfall with slide down. Parking: The swimming hole is located between Sandisfield Town Office and the post office. There is one dirt pull-off space near the swimming hole. The easiest parking is at the Town Offic...
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  • Altamont, New York

    Wolf Creek Falls Preserve White Trail Loop

    3.0
    1.93 mi / 256 ft gain
    Over 3 miles of trails provide access to all parts of the preserve, and end up winding through mixed terrain including a wetland, waterfalls, and old stone walls. The property crosses the Bozenkill Road at two points on either side of private parcels (with beautiful homes), so be vigilant there; ...
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  • Windham, New York

    Escarpment Trail

    21.97 mi / 5282 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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  • Elka Park, New York

    Hike to Huckleberry Point

    4.5
    4.5 mi / 644 ft gain
    This is a 4.5 mile hike that is great for hikers of all skill levels. Because it is short and not overly difficult, beginners will enjoy this hike. There are some steep sections that will get your heart pumping, though, and a stunning payoff is waiting for you at the end.From the trailhead, follo...
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