Skiing
The parks below provide excellent opportunities for cross-country skiing including some groomed (and at least grooved) trails. For more info, check in with Pawling Cycle & Sport for details and gear. For downhill skiers and snowboarders, Thunder Ridge has groomed trails and snow-making capabilities. 

Appalachian Trail
Pawling Nature Reserve
Lakeside Park
Clarence Fahnestock State Park

Appalachian Trail 

One of America's longest, oldest and best-known trails, the 2,175-mile Appalachian Trail makes it's way through Pawling and the surrounding area across a variety of terrain and ecosystems. Conceived in 1921 and first completed in 1937, it traverses the wild, scenic, wooded, pastoral, and culturally significant lands of the Appalachian Mountains.

There are a number of sections one can hike in the area ranging from 45 minutes to a full day's hike of multiple sections. And if you keep on walking you might end up in Maine or Georgia! 

park service website
appalachian trail conservancy website
wikipedia entry
interactive trail map
google map of trailheads

Pawling Nature Reserve 

Hikers of all levels will enjoy the steep terrain, which includes more than ten miles of marked trails that range from moderate one-hour strolls to strenuous day-long treks. Explore a microcosm of diverse natural communities of the 1,060 acre preserve. 

In the reserve's gorge, Duell Hollow Brook cascades down the rocks and The Appalachian Trail winds through stands of red pines, eastern hemlocks, and mixed hardwoods. Farther up the ridge, a hillside of beech trees slopes down into a yellow birch forest. And at the ridgetop, chestnut oaks, lichens and mosses grace the rocky soil and compliment stunning views of Great Swamp and Harlem Valley below.

website
map
google map of trailhead

Lakeside Park 

With approximately 300 acres of trails, beautiful Green Mountain Lake and sports facilities including a beach and tennis courts Lakeside Park is one of the great outdoor assets of Pawling. A trail system circumnavigates the lake making for an easily accessible one or two hour hike, snowshoe or cross-country ski along the water and through pine forests and open meadow. 

google map

Clarence Fahnestock State Park 

This 14,086 acre park, covering land in Putnam and Dutchess counties, boasts hiking trails, a beautiful beach, picnic areas, scenic campground, and abundant opportunities for cross-country skiing, boating, hunting, fishing, and birding. The park is also home to the Taconic Outdoor Education Center which provides high quality environmental programming and Fahnestock Winter Park which includes 15 kilometers of groomed trails for cross country skiing and snowshoeing, and an area for sledding. 

website
trail map
google map of trailhead