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Greenwich, New York

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

Top Hiking Spots in and near Greenwich

  • Shaftsbury, Vermont

    Hike Around Lake Shaftsbury

    1.3 mi / 42 ft gain
    Lake Shaftsbury State Park is a small park in Southern Vermont between Bennington and Manchester. It is well-loved by locals as swimming spot in the summer, especially for families with kids.  Less well known is the nature trail that meanders around the perimeter of the lake. While only a mile in...
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  • Dorset, Vermont

    Hike 'The Merck'

    4.0
    2.5 mi
    Of the 10 trails at The Merck, The Wildlife Trail is a great hike through the forest that offers you the best way to see wildlife, streams and tracks. You can do the whole hike as a loop in about 2-2 1/2 hours or shorten it up with some shortcuts if you just want a quick hike. Great for family ...
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  • Cropseyville, New York

    Hike Dickinson Hill Fire Tower

    4.5
    3 mi / 200 ft gain
    Once you drive onto N. Long Pond Road you will follow it appproximately 1.5 miles to the end. From the parking you can take the short walk back on the road to the start of the trail. The trail is actually a rough Fire Tower Road. You will follow this for about 1.3 miles. Here you will see a se...
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  • Glen Road, Vermont

    Hike the Lye Brook Falls Trail

    4.0
    4.7 mi / 938 ft gain
    The Lye Brook Falls Trail is a 4.7 mile hike through scenic trails just outside of Manchester Center, Vermont. The trail is open year-round, but the best time to go is during spring blooms or to see the fall colors. This hike is family friendly and fun for all ages. Dogs are allowed on this trail...
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  • Woodford, Vermont

    Woodford State Park Loop

    2.41 mi / 203 ft gain
    A great loop for the summer, Woodford is also amazing when winter winter comes to the State Park. It also comes earlier than just about anywhere else in Southern Vermont. At 2,400 feet above sea level, this is an easy spot to find winter without spending a fortune at the local ski resorts. Woodfo...
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  • Schenectady, New York

    Hike the Lisha Kill Preserve Loop

    5.0
    2.3 mi / 324 ft gain
    This 2.3 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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  • Hadley, New York

    Hike the Adirondack's Hadley Mountain

    5.0
    3.6 mi / 1545 ft gain
    Hadley Mountain historically has faced its share of forest fires. The fires left thin soil, leading to more exposed rock on this fairly quick, scenic hike. Due to the rockiness, when you're thinking about heading out for this hike, be sure to grab a sturdy pair of hiking boots or at least your st...
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  • Poultney, Vermont

    Camp on Mount St. Catherine

    5.0
    Looking for the best view in all of Poultney, Vermont? Look no further than Lake St. Catherine Mountain. Located within Deane's Nature Preserve, this fast and easy hike tops as one of the best views and camping spots for the little time and energy needed to reach the summit. Only 30-45 minutes fr...
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  • Fort Ann, New York

    Hike to Shelving Rock Falls

    1 mi / 50 ft gain
    The hike to beautiful Shelving Rock Falls is only a half mile and well worth the side trip if visiting the east side of Lake George.  Shelving Rock Road, the road to the parking area, is long, winding, and unpaved, but maintained pretty well and passable in a sedan. You'll want to take the road a...
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  • Fort Ann, New York

    Hike Shelving Rock Mountain

    3.4 mi / 650 ft gain
    The trailhead for Shelving Rock Mountain has enough room for about five cars but additional parking can be found on the road leading to it. Be sure to sign the log book and begin the hike by passing around the "stop" car barrier.The trail starts off following a small stream (on your right) but yo...
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  • Albany, New York

    Blueberry Hill East

    1.73 mi / 59 ft gain
    Blueberry Hill East is a loop trail where you may see beautiful wildflowers located near Albany, New York.
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  • Albany, New York

    Blueberry Hill West Red and Yellow Trail

    1.37 mi / 52 ft gain
    Blueberry Hill West Red and Yellow Trail is a loop trail where you may see beautiful wildflowers located near Albany, New York.
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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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  • Williamstown, Massachusetts

    Hike Mt. Greylock via Money Brook Trail

    9.7 mi / 3034 ft gain
    Park in the parking lot on Hopper Rd. Walk to the end of the road where you will find the Hopper Trailhead. Take the right fork. The Money Brook trail will take you to a waterfall, the Mt. Greylock summit, and back to the end of Hopper Rd. The trail is long but worth the hike, exploring parts of ...
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  • Bolton, New York

    Hike Cat & Thomas Mountains Preserve

    5.0
    5.8 mi
    There are a few ways to approach these two peaks. We chose to do a traverse using two vehicles.Starting at Edgecomb Pond Rd you will park along the road. There will be a sign and yellow discs directing you to the start of the trail. The first 0.4 miles is following a dirt road. You will then ...
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  • Williamstown, Massachusetts

    Hike the March Cataract Falls Trail

    4.0
    2.2 mi / 511 ft gain
    Park at the Junction of Sperry Rd and Rockwell Rd. To get to the trailhead, hike along Sperry Road for about 30 minutes. (Not to the end of the road, see map below.) Then hike along the March Cataract Trail, an out-and-back. You can bring dogs on leash. The trail is short but steep in some parts ...
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