Trails Near Bennington, VT

Albany Pine Bush Preserve

Located within the Capital District Region, the Albany Pine Bush Preserve contains one of the best remaining examples of an inland pine-barrens ecosystem in the world.


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  • 4.5 miles
  • Albany, NY

Arrowhead Recreation Park

Arrohead Recreation Park is open year round offers groomed slopes that can be skied or snowboarded during the winter time and also has a public tubing area open from january to march. During the warm months Arrowhead offers several miles of recreational hiking trails that open to mountain bikers.


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  • 2.5 miles
  • Claremont, NH

Ashley Reservoir Loop

Ashley Reservoir Loop is a 3.7 mile loop trail located near Holyoke, Massachusetts that features a lake and is good for all skill levels. The trail is primarily used for nature trips, road biking, trail running & walking and is accessible year-round.


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  • 3.7 miles
  • Holyoke, MA

Black North Wma

Black North WMA is an out and back trail located near Acworth, New Hampshire that features a river and is good for all skill levels. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • Acworth, NH

Bobby Woodman Trail

Bobby Woodman Trail is a 1 mile point-to-point trail located near Claremont, New Hampshire that features beautiful wild flowers and is good for all skill levels. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 1 miles
  • Claremont, NH

Buck Mountain Trail

The trail to the summit is 3.3 miles one-way and gains 2,000 feet elevation, and is well traveled and well marked. This hike is moderate and you should give yourself plenty of time to complete it.


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  • 6.6 miles
  • Kattskill Bay, NY

Ceda-T Trail

Ceda-T Trail is a 4 mile loop trail located near Charlestown, New Hampshire that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 4 miles
  • Charlestown, NH

Cherry Plain State Park Campground

A great State Park that offers a beach, pavilions, facilities, camping and multiple trails to choose from (short to longer).


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  • 3 miles
  • Petersburg, NY

Cohoes Falls

cohoes falls is a 3.4 mile trail located near Waterford, New York. The trail is rated as moderate and primarily used for trail running.


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  • 3.4 miles
  • Waterford, NY

Fall Mountain State Forest

Fall Mountain State Forest is a 6 mile loop trail located near Alstead, New Hampshire that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 6 miles
  • Alstead, NH

Green Mountain Towers

Green Mountain Towers is a 2.5 mile out and back trail located near Claremont, New Hampshire that features a river and is rated as moderate. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 2.5 miles
  • Claremont, NH

Green Mountain Trail

Green Mountain Trail is a 6 mile loop trail located near Danby, Vermont and is rated as difficult. The trail offers a number of activity options and is accessible year-round.


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  • 6 miles
  • Danby, VT

H. Newman Marsh Memorial Trail / Sanderson Brook Falls

This is a terrific wooded trail taking you into the Blandford/ Chester State Forest through thick wooded areas a beautiful vista, especially early spring and fall and to the beautiful Sanderson Brook Falls.


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  • 4.3 miles
  • Chester, MA

Hand Hollow Conservation Area

walking, hiking, snowshoe trails as well as birding and fishing


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  • 3 miles
  • East Chatham, NY

Hang Glider Trail

Hang Glider Trail is a 7 mile out and back trail located near Brownsville, Vermont that features beautiful wild flowers and is rated as difficult. The trail is primarily used for hiking, snowshoeing, trail running & walking and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 7 miles
  • Brownsville, VT

Hannacroix Creek Preserve

waterfall, scenic view, easy walk


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  • 2.5 miles
  • West Coxsackie, NY

Haystack Mountain Trail

Haystack Mountain Trail is a 4 mile out and back trail located near West Rupert, Vermont and is rated as moderate. The trail offers a number of activity options and is accessible year-round.


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  • 4 miles
  • West Rupert, VT

Huyck Preserve Trail System

The Huyck Preserve has 12 miles of trails open to the public daily dawn to dusk. Trails snake along the Rensselaerville falls, meander through peaceful old-growth forests, circumvent both Lake Myosotis and Lincoln Pond, and wind through several 80+ year old pine and spruce plantations.


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  • 12 miles
  • Rensselaerville, NY

Knapp Pond

Knapp Pond is an out and back trail located near Cavendish, Vermont that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • Cavendish, VT

Lisha Kill Preserve

beautiful forest, small creek, easy walk, close to home


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  • 2 miles
  • Schenectady, NY

Little Ascutney Wma

Little Ascutney WMA is a 4 mile loop trail located near Reading, Vermont that features a river and is rated as moderate. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 4 miles
  • Reading, VT

Mohawk-Hudson Bikeway (Erie Canal, Eastern Section)

Easy to use paved trail. Perfect for biking, walking, jogging.


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  • 36.5 miles
  • Albany, NY

Moody Park Loop

Moody Park Loop is a 2 mile loop trail located near Claremont, New Hampshire that features beautiful wild flowers and is good for all skill levels. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 2 miles
  • Claremont, NH

Mount Ephraim

Mount Ephraim is a 4 mile out and back trail located near Springfield, Vermont that features a river and is rated as moderate. The trail is primarily used for hiking, snowshoeing, trail running & walking and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 4 miles
  • Springfield, VT

Ooms Conservation Area

Open conservation area with loop trails


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  • 3 miles
  • Old Chatham, NY

Pine Bush

Pine Bush is a preserve over 3000 acres large with many different sections to run.


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  • Albany, NY

Quabbin Reservoir Gates 11-12 Loop

Quabbin Reservoir Gates 11-12 Loop is a 4.5 mile loop trail that features a lake and is rated as moderate. The trail is primarily used for hiking, nature trips, trail running & walking and is accessible year-round.


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  • 4.5 miles
  • Pelham, MA

Roland Preserve

Roland Preserve is a 1.5 mile trail located near Ballston Spa, New York. The trail offers a number of activity options.


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  • 1.5 miles
  • Ballston Spa, NY

Ruffin'S Ridgeway Loop

Ruffin's Ridgeway Loop is a 4 mile loop trail located near Claremont, New Hampshire that features beautiful wild flowers and is rated as moderate. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 4 miles
  • Claremont, NH

Schodack Island State Park Trail

schodack island is a 5.0 mile trail located near Schodack, New York. The trail is primarily used for hiking.


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  • 5 miles
  • Schodack, NY

Shelving Rock Mtn.

Shelving Rock Mtn. is a 1.6 mile out and back trail located near Fort Ann, New York that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.


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  • 1.6 miles
  • Fort Ann, NY

Slot Trail

Slot Trail is a 7 mile out and back trail located near Windsor, Vermont that features a waterfall and is rated as moderate. The trail is primarily used for hiking, snowshoeing, trail running & walking and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 7 miles
  • Windsor, VT

Spire Mountain Trail On Grant Mountain

Spire Mountain trail on Grant mtn is an out and back trail located near Gansevoort, New York that features a great forest setting and is rated as difficult. The trail is primarily used for mountain biking & trail running and is accessible year-round.


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  • Gansevoort, NY

Springweather Dams Via Sand Hill

To complete the full loop you must cross back over the river just before the Power Dam, during autumn and winter this is pretty simple as it will be very shallow or completely frozen over however, in the spring and early summer the water will be much higher and faster obviously making crossing risky


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  • 8 miles
  • Perkinsville, VT

Table Rock Trail Fall Mountain

Table Rock Trail Fall Mountain is a 2 mile out and back trail located near North Walpole, New Hampshire that features beautiful wild flowers and is rated as moderate. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 2 miles
  • North Walpole, NH

Taconic Crest Trail

The Taconic Crest Trail is a 35.4 mile ridge trail that skirts along the NY/MA/VT borders with varied terrains and entry points.


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  • 35.4 miles
  • Petersburg, NY

Tollgate To Thatcher Park

A 10 mile course. The first 6.5 miles are fairly flat and the last 3 miles are all uphill.


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  • 10 miles
  • Albany, NY

Wilkinson National Recreation Trail

Here in the autumn of 1777, American forces met, defeated and forced a major British army to surrender. This crucial American victory in the Battle of Saratoga renewed patriots hopes for independence, secured essential foreign recognition and support, and forever changed the face of the world.


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  • 4.1 miles
  • Stillwater, NY

Wilson M Powell Wildlife Preserve

A great preserve for birding and hiking - 145 acres of fauna and flora diversity.


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  • 2 miles
  • Old Chatham, NY

Wilton Wildlife Preserve(Fox Trails)

wilton wildlife preserve(fox trails) is located near Wilton, New York. The trail is good for all skill levels offers a number of activity options. Dogs are also able to use this trail but must be kept on leash.


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  • Wilton, NY

Windsor Trail

Windsor Trail is a 3.4 mile out and back trail located near Windsor, Vermont that features a waterfall and is rated as difficult. The trail offers a number of activity options and is accessible from January until January. Dogs are also able to use this trail but must be kept on leash.


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  • 3.4 miles
  • Windsor, VT


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