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Bennington, Vermont

Top Spots in and near Bennington

  • Wallingford, Vermont

    Hike the White Rocks Ice Beds Trail

    1.6 mi / 180 ft gain
    This 1.6 mile round trip hike starts from the Ice Beds parking lot in the Green Mountain National Forest in Vermont.  The trailhead is close to the parking lot entrance, following the blue-blazed trail.  Be sure to read the signs, as the far trailhead is a hike to the cliffs, not the ice beds. Af...
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  • Deerfield, Massachusetts

    South Sugarloaf Trail

    1.48 mi / 404 ft gain
    South Sugarloaf Trail is a loop trail that takes you by a river located near South Deerfield, Massachusetts.
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  • Stockbridge, Massachusetts

    Laura's Tower and Ice Glen

    5.0
    2.4 mi / 676 ft gain
    You will park at the end of Park Street in Stockbridge, Massachusetts.  From the parking are you will cross a beautiful bridge over the Housatonic River.  The trail crosses railroad tracks and immediately begins to climb into the woods.  You will reach a split in the trail, a left will take you...
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  • Erving, Massachusetts

    Rattlesnake Loop to Red Trail

    1.97 mi / 676 ft gain
    Rattlesnake Loop to Red Trail is a loop trail that provides a good opportunity to view wildlife located near Erving, Massachusetts.
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  • Schenectady, New York

    Hike Plotter Kill Preserve

    4.3
    5.5 mi / 820 ft gain
    There are a few entries into the preserve' however, this hike has you entering off of Mariaville Road. There is a kiosk here and you will enter on the Red trail. Shortly after you can go out and back on the Blue trail to view the Upper and Lower Falls from lookouts above. Once back to the Red t...
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  • Voorheesville, New York

    Hike the Indian Ladder Trail

    4.5
    3.5 mi / 200 ft gain
    There are many parking areas within the park. Park at the overlook parking. From here you head west following the wood fence. This is the Cliff Top trail. Approximately after walking 0.5 miles you will reach the stairs that will lead you to the base of the cliffs. This marks the start of the...
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  • Great Barrington, Massachusetts

    Hike Monument Mountain

    4.0
    2 mi / 720 ft gain
    At 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...
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  • Voorheesville, New York

    Hike the Keleher Preserve Loop

    2.0
    3 mi / 1636 ft gain
    The historic preserve is operated by the Mohawk Hudson Land Conservancy, so trails are clearly marked and extremely well maintained. There are features of the original farm that the land was used for from the 18th Century, including hand-thrown stone walls and an old logging road that cuts throug...
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  • Altamont, New York

    Hike through the Wolf Creek Falls Preserve

    3.0
    3 mi / 200 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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  • Great Barrington, Massachusetts

    Mt. Wilcox and Beartown Mountain Trail Loop

    5.0
    9.29 mi / 981 ft gain
    Mt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.
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  • Hudson, New York

    High Falls Conservation Area Loop

    1.41 mi / 194 ft gain
    High Falls Conservation Area Loop is a loop trail that takes you by a waterfall located near Philmont, New York.
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