Trails Near Milton, NY

Bashakill

Bashakill is a 10 mile loop trail located near Wurtsboro, New York that features a lake and is only recommended for very experienced outdoorsmen. The trail offers a number of activity options and is accessible from April until December.


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  • 10 miles
  • Wurtsboro, NY

Baxter Mountain Trail

Baxter Mountain trail is a 2 mile out and back trail located near Roscoe, New York that offers the chance to see wildlife. The trail is rated as moderate and primarily used for birding, hiking, trail running & walking. Dogs are also able to use this trail but must be kept on leash.


Profile
  • 2 miles
  • Roscoe, NY

Blue Mountain Twin Summits Trail

Blue Mountain Twin Summits Trail is a 5 mile loop trail located near Cortlandt Manor, New York and is rated as moderate. The trail is primarily used for hiking, mountain biking & trail running and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.


Profile
  • 5 miles
  • Cortlandt Manor, NY

Bonticou Crag Hike (Mohonk Preserve)

Travel from open fields through the woods and hike to the top of a prominent, stark-white crag overlooking the valley. (Optional, challenging rock scramble up.) Note that there is a small fee, per person, as this is on the Mohonk Preserve.


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  • 3.5 miles
  • High Falls, NY

Bronx River Pathway

Bronx River Pathway is a 16.3 mile point-to-point trail located near Valhalla, New York that features a waterfall. The trail offers a number of activity options. Dogs are also able to use this trail but must be kept on leash.


Profile
  • 16.3 miles
  • Valhalla, NY

Buck Mountain Trail

Buck Mountain Trail is a 7 mile out and back trail located near Ringwood, New Jersey that features a river and is rated as difficult. The trail is primarily used for hiking, rock climbing & trail running and is accessible from April until October. Dogs are also able to use this trail.


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  • 7 miles
  • Ringwood, NJ

Burr Pond

Burr Pond is a 2.7 mile loop trail located near Torrington, Connecticut that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible from April until October. Dogs are also able to use this trail but must be kept on leash.


Profile
  • 2.7 miles
  • Torrington, CT

Campbell Falls

Campbell Falls is one of the top waterfalls in Mass. The combination of the short and easy hike and the zig zagging plunge through a gorge makes this waterfall a great area to visit and photograph.


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  • 0.2 miles
  • Norfolk, CT

Catfish Loop Trail

One of the many loop trails in the park. Great 5 mile loop. Red Blaze


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  • 4.31 miles
  • Putnam Valley, NY

Chadwick Lake

It is a very easy walk. Beautiful lake, okay fishing, row boating, playground, roller rink, biking. The trail is gravel (con) can be busy, good for running, walking or biking


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  • 4 miles
  • Newburgh, NY

Connecticut Coast Scenic Drive

Connecticut Coast Scenic Drive is a 134 mile point-to-point trail located near Stamford, Connecticut 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.


Profile
  • 134 miles
  • Stamford, CT

Devil'S Den Concourse

Devil's Den Concourse is a 8 mile loop trail located near Weston, Connecticut and is good for all skill levels. The trail is primarily used for hiking & trail running and is accessible year-round.


Profile
  • 8 miles
  • Weston, CT

Devil'S Den Preserve Trail

Devil's Den Preserve Trail is a 7.0 mile loop trail located near Weston, Connecticut and is good for all skill levels. The trail is primarily used for hiking and is accessible year-round.


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  • 4.5 miles
  • Weston, CT

Earl Reservoir Loop

Earl Reservoir Loop is a 1.2 mile loop trail located near Highland Mills, New York that offers scenic views 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.


Profile
  • 1.2 miles
  • Highland Mills, NY

Enchanted Trail

A public trail blazed with diamond-shaped yellow markers that crosses Bethel from Meckauer Park in the north to Huntington Park in the south


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  • Bethel, CT

Escarpment Trail

Amazing Catskills and HudsonValley views from multiple view points along the way. Significant climbs and descents with the occasional rock scramble.


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  • 23 miles
  • Jewett, NY

Fahnestock Trail

One of if not the main trail in the park. Blue Blazing.


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  • 6.09 miles
  • Philipstown, NY

Goose Pond Mountain - Bike Trails

Goose Pond Mountain - Bike Trails is a 7.5 mile loop trail located near Chester, New York that features a river and is rated as moderate. 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.


Profile
  • 7.5 miles
  • Chester, NY

Great Ledge- Redding Land Trust

Great trail connecting the Nature Conservancy's Devils Den and the Centennial Watershed State Forest's Saugatuck Valley Trail


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  • Redding, CT

Harlem Valley Rail Trail

Harlem Valley Rail Trail is a 11 mile point-to-point trail located near Copake Falls, New York. The trail is good for all skill levels offers a number of activity options.


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  • 11 miles
  • Copake Falls, NY

Hemlock Hills & Pine Mountain

Pine Mountain Reserve is a 368 acre[1] open space in Ridgefield, Connecticut. The space has many trails, trail heads and also one of Ridgefield's highest points, at 1,021 feet (311 m)[2] above sea level.


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  • 0.4 miles
  • Ridgefield, CT

Highlander Trail

A great trail that leads from Maple Road to the high school and Westbrook Elementary School and halfway down Highlander Road.


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  • 0.5 miles
  • West Milford, NJ

Jockey Hill

The majority of trails at Jockey Hill are single track, varying in difficulty from fairly flat cruises over rocks & roots, to super-technical trails running along sloped hills with logs, roots, water, mud and trees closer than a handlebars width to negotiate.


Profile
  • 11 miles
  • Kingston, NY

Larkin State Bridle Trail

Larkin State Bridle Trail is a 10.3 mile point-to-point trail located near Oxford, Connecticut. The trail is good for all skill levels and primarily used for hiking, mountain biking, trail running & walking. Horses are also able to use this trail.


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  • 10.3 miles
  • Oxford, CT

Marian Yarrow Sanctuary (The Nature Conservancy)

Travel through hardwood forests to discover wetlands, lakes and streams.


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  • 1.5 miles
  • Katonah, NY

Millbrook Mountain

Millbrook Mountain is a 4.7 mile loop trail located near Kerhonkson, New York that features beautiful wild flowers and is rated as moderate. The trail offers a number of activity options and is accessible from April until November.


Profile
  • 4.7 miles
  • Kerhonkson, NY

Moonbeams Preserve Trail

An Orange County Land Trust nature preserve that includes 150 acres of fields, forest and wetlands located at the base of the Shawangunk Ridge and bordering the Shawangunk Kill. Great views of the Shawangunk Kill.


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  • Middletown, NY

Mount Beacon

Mount Beacon is a 3.5 mile out and back trail located near Beacon, New York and is rated as moderate. It is a challenging uphill climb that pays off in spades. Fantastic panoramic views of the Hudson, Newburgh, and Beacon. The trail is primarily used for hiking and is accessible year-round.


Profile
  • 3.5 miles
  • Beacon, NY

Mount Holly Preserve Trail (The Nature Conservancy)

Mount Holly Preserve Trail (The Nature Conservancy) is a 1.7 mile loop trail located near Katonah, New York and is good for all skill levels. The trail offers a number of activity options and is accessible year-round.


Profile
  • 1.7 miles
  • Katonah, NY

Mt Loop

mt loop is a 3 mile trail located near Nyack, New York. The trail is primarily used for trail running.


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  • 3 miles
  • Nyack, NY

Nature Trails

White Memorial Foundation: Nature Trails. There are 35 miles of trails on 4000 acres of fields, waters and woodlands. There are also 3 campgrounds, a museum and special areas for large outdoor gatherings.


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  • 7.6 miles
  • Litchfield, CT

Ninham Mountain Mua

Ninham Mountain MUA is a 8 mile out and back trail located near Carmel, New York that features a river and is good for all skill levels. The trail offers a number of activity options and is accessible from March until November. Dogs are also able to use this trail but must be kept on leash.


Profile
  • 8 miles
  • Carmel, NY

North County Trailway

North County Trailway is a 29.4 mile paved rail trail from Elmsford at the south end to Brewster at the northern end. The trail is good for all skill levels and primarily used for road biking & trail running.


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  • 29.4 miles
  • Millwood, NY

Old Croton Aqueduct Trailway: Yonkers To Croton Dam In Three Sections

Old Croton Aqueduct Trailway: Yonkers to Croton Dam in Three Sections is a 26.2 mile point-to-point trail located near Tarrytown, New York and is good for all skill levels. The trail is primarily used for hiking, mountain biking, trail running & walking and is accessible year-round.


Profile
  • 26.2 miles
  • Tarrytown, NY

Onteora Lake

About a dozen miles of superb singletrack. Rocky sharkfins of slate. Lots of crags and pine. Scenic lakes. Some powerclimbs but not much elevation change


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  • 10 miles
  • Kingston, NY

Pootatuck State Forest

Hilly terrain with great features.


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  • New Fairfield, CT

Putnam Memorial State Park

This was the site of the Continental Army's 1779 winter encampment under the command of General Israel Putnam. The site consists of remains of the encampment, reconstructed log buildings, and a museum. Connecticut's oldest State Park!


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  • Redding, CT

Railtrail

railtrail is a 2.1 mile trail located near Nyack, New York. The trail is primarily used for trail running.


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  • 2.1 miles
  • Nyack, NY

Shelton Rec Trail

Shelton Rec Trail is a 9.3 mile out and back trail located near Shelton, Connecticut. The trail is rated as moderate offers a number of activity options.


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  • 9.3 miles
  • Shelton, CT

Shepherd Lake

Shepherd Lake is located near Ringwood, New Jersey that features a waterfall and is rated as moderate. The trail offers a number of activity options and is accessible from April until October.


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  • Ringwood, NJ

Sierra Trail To Freedom Trail

Sierra trail to Freedom Trail is a 3.4 mile trail located near Fishkill, New York. The trail is primarily used for hiking & trail running.


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  • 3.4 miles
  • Fishkill, NY

Stewart State Forest Trails

The 6700-acres of Stewart State Forest are unique in the northeast and increasingly rare in the Hudson Valley. A mix of wetlands, fields and woods, the site includes 18 miles of gravel roads and over 22 miles of major trails which provide unparalleled recreation.


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  • 18 miles
  • Rock Tavern, NY

Strauss & Giddings Preserves

Interconnected land parcels.


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  • Sherman, CT

Taconic State Park: Copake Falls Area Campground

Taconic State Park: Copake Falls Area Campground is located near Copake Falls, New York and features a lake. The trail offers a number of activity options. Dogs are also able to use this trail but must be kept on leash.


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  • Copake Falls, NY

Tarrywile Park

The Park has over 21 miles of trails, ponds & numerous vistas.


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  • 2.9 miles
  • Danbury, CT

The Mianus Maze

The Mianus Maze is a 14 mile loop trail located near Stamford, Connecticut that features a river. 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.


Profile
  • 14 miles
  • Stamford, CT

Thompson Pond

Thompson Pond is a 2.4 mile loop trail located near Pine Plains, New York that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible from May until October.


Profile
  • 2.4 miles
  • Pine Plains, NY

Timp Trail

I started at the Anthony Wayne Recreation Area and hiked into Bear Mountain State Park via the Fawn trail. The Fawn trail intersects the Timp Torne trail which I followed South up the ridge leading to Western Mountain then turns East towards Jones Point overlooking the Hudson River.


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  • 8 miles
  • Tomkins Cove, NY

Topstone Park

topstone park is located near Redding, Connecticut. The trail is good for all skill levels and primarily used for hiking, trail running & walking. Dogs are also able to use this trail but must be kept on leash.


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  • Redding, CT

Trumbull / Old Mine Park

Trumbull / Old Mine Park is a 11 mile loop trail located near Trumbull, Connecticut. The trail runs along the West Branch of the Pequonnock River it is a prime river to catch trophy trout. The trail is primarily used for mountain biking.Dogs are also able to use this trail.


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  • 11 miles
  • Trumbull, CT

Turkey Mountain Trail

Turkey Mountain Trail is a loop trail located near Yorktown Heights, New York that offers scenic views. The trail is rated as moderate and primarily used for birding, hiking & trail running.


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  • Yorktown Heights, NY

Wallkill Valley Rail Trail

Wallkill Valley Rail Trail is a 15.8 mile point-to-point trail located near New Paltz, New York. The trail is good for all skill levels offers a number of activity options.


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  • 15.8 miles
  • New Paltz, NY


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