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Artists Rock

Located at North-South Lake state park. If you bring your dog you must have its papers to get into the park. Swimming and kayaking is also available. Artist Rock is a fantastic trail with lots of vistas, you can make it a short hike or a very long one. More information is available at park’s entrance booth.
GPS: North-South Lake park NY

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K. Wilson state park

A perfect place for snowshoeing. No entrance fee in the winter months.
GPS: 859 Wittenberg Road, Mt. Tremper, NY 12457

 
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Comeau Property

Easy walk in the woods and along the river. Right from the center of Woodstock.
Address: 95 Comeau Drive, Woodstock, NY

 
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Ashokan Reservoir

Plenty of places to bike, walk, skate around the reservoir. Dogs not allowed.
GPS: 27 B W S Rd, Kingston, NY 12401

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Overlook Mountain

A wide, popular trail about 1.5 hour straight up. With ruins of an old hotel along the trail. The top is well-worth the effort . There’s a fire tower to climb even higher. On a nice day you can see four states (NY, NJ, MA, CT), parking is at : 353 Meads Mountain Rd, Woodstock, NY 12498 On a nice day the lot gets filled up fast.
GPS: 353 Meads Mountain Rd, Woodstock, NY 12498

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Ashokan Rail-To-Trail

The ever so popular trail, 11 miles long perfect for biking or walking. For nicest part enter at the Boiceville entrance. Google Ashokan rail trail