Middlebury, Vermont

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

Top Hiking Spots in and near Middlebury

  • Clemons, New York

    Black Mountain Loop

    6.79 mi / 1319 ft gain
    Black Mountain is located on the Eastern side of Lake George and is the tallest mountain above Lake George. The trailhead is located on Pike Brook Road (off from Hulett's Rd, Route 6) in Clemons, NY. The parking area is about one mile up Pike Brook Road, on the right. This hike to Black Mountain...
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  • Jericho, Vermont

    Americana and Mobbs Hill Loop

    4.0
    2.83 mi / 515 ft gain
    Americana and Mobbs Hill Loop is a loop trail that is moderately difficult located near Jericho, Vermont.
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  • Keene Valley, New York

    Rooster Comb Mountain

    4.69 mi / 1673 ft gain
    Take in two unique views of the Adirondacks on one hike. Rooster Comb offers a great 5.2 mile round trip hike that gives you some unique vantage points. Starting from the parking lot you cross over a nice wooden bridge to the trail registry. Remember to sign in. Next you'll come up on a pond in w...
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  • Keene Valley, New York

    Climb Haystack, Basin & Saddleback

    18 mi
    This hike starts in the Garden Parking Lot in Keene Valley, NY. The Garden parking lot (operated by the town of Keene) costs $7 per day from late April through the end of October (2014 rate). An attendant is on duty 1 p.m.-7 p.m. Fridays and 7 a.m.-7 p.m. Saturdays, Sundays, and holidays. Town e...
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  • Montpelier, Vermont

    Stone Tower via State House Trail

    1.22 mi / 356.3 ft gain
    Start at the Vermont State House in Montpelier and hike the State House Trail to the stone observation tower. There are 7 miles of trails in Hubbard Park, but the trail from the State House to the tower is 0.5 miles one-way. Started in 1915 and completed in 1930, the 54-foot-tall Hubbard Park ...
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  • Waterbury Center, Vermont

    Hike Mt. Hunger

    4.5
    4.2 mi / 2263 ft gain
    Mt Hunger stands at 3540 ft and face Vermont's tallest mountain, Mt Mansfield. At 45 min drive from Burlington, this is a challenging out and back hike.  The views it offers and the waterfalls you will find along the path, makes it a good alternative to the overcrowded trails of Mt Mansfield. Th...
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  • Fort Ann, New York

    Sleeping Beauty and Bumps & Fishbrook Ponds

    6.16 mi / 1138 ft gain
    Parking is available at the end of Dacy Clearing Rd. There are great primitive campsites throughout the area. In winter and mud season you will have to park at the start of Dacy Clearing Rd which adds 1.6 miles each way. From the parking clearing, turn right passing through a gate. Soon you r...
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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

    Shelving Rock Mountain

    3.09 mi / 581 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 ...
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  • Fort Ann, New York

    Shelving Rock Falls

    0.63 mi / 46 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 ...
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  • North Elba, New York

    Hike Cascade & Porter Mountains

    4.7
    4.8 mi / 1900 ft gain
    Cascade 4,098ft and Porter 4,084ft are two easy peaks which are usually hiked together. The trail starts on Rt 73 and you starts climbing up slowly but not challenging at all. Is 2.4 mIles to summit of cascade, the last 0.2 miles is a open rock scrambling but I'm the winter when the weather is b...
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  • Fort Ann, New York

    Buck Mountain via Shelving Rock Road

    4.44 mi / 1145 ft gain
    There are a few options for this mountain. The route described is the easiest approach and therefore the nicest for a sunset hike. Starting at the trailhead on Shelving Rock Road the sign will read 2.5 miles to the summit. The trail is easy to follow and marked with blue discs. Gentle grade for ...
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  • Ausable Chasm, New York

    Ausable Chasm

    1.84 mi / 210 ft gain
    Ausable Canyon is known as The Grand Canyon of the Adirondacks, this park offers a variety of adventure!! Enjoy the beauty and geologic history as a day trip or spend a few days. Ausable Chasm offers a variety of accommodations including camping, cabins or a motel. The recreation center at the...
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  • Bolton, New York

    Cat & Thomas Mountains

    5.0
    5.67 mi / 1280 ft gain
    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 the...
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  • Bolton Landing, New York

    The Pinnacle via Red Trail

    5.0
    2.06 mi / 541 ft gain
    The Pinnacle via Red Trail is a great, easy hike with views of Lake George, near Bolton Landing, NY. There is a small parking lot at the trailhead with overflow cars parking alongside the street.  This hike is along an out-and-back trail that is a little over 2 miles total and full of beautiful ...
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  • 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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