Hiking
There are a great number of places to enjoy a hike in the area. One of the world's most famous trails passes through Pawling, the Appalachian Train and there are a number of premier spots for a walk in the woods. All of these spots make for great snowshoeing in the winter. See below for more information.
Appalachian Trail • Pawling Nature Preserve • Stone Church • Roger Perry Preserve • Great Thicket National Wildlife Preserve • Ninham Mountain • Lakeside Park • Clarence Fahnestock State Park • Michael Ciaiola Conservation Area • Wonder Lake State Park • Macedonia Brook 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 Preserve
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.
official website
trail map
nature conservancy website
google map of trailhead
Stone Church
One of the areas natural wonders, Stone Church in Dover, NY is located in a 60 acres preserve and features a large stone entrance in the shape of an arch leading to a cavern with a 30-foot waterfall inside the cavern. Pequot Chief Sassacus is said to have hidden in the cave called Dover Stone Church, escaping English soldiers after the massacre at New London. The site is also across the street from the Dover Plains Metro North stop which may be convenient for travelers.
https://hikethehudsonvalley.com/hikes/dover-stone-church/
visitor's guide
google map of trailhead
Roger Perry Preserve
Once known locally as the White Sands of Dover, this 117-acre site in Dover Plains features a series of eroded limestone ridges and bedrock outcrops crested by cottonwood trees. Sparkling white sand covers much of the land, punctuated by limestone outcroppings, dense conifer forest, and secluded fens. This landscape mosaic is unlike any other habitat in the region. Due to the sensitivity of the fens to trampling, please stay on the trail.
Great Thicket National Wildlife Preserve
This beautiful preserve was formerly the Nature Conservancy's Nellie Hill Preserve. From atop this 143-acre preserve's rocky summit of a 120-foot calcareous cliff, enjoy gorgeous views of pocket grasslands that resemble savannas, sloping meadows, a rich oak woodland and a limestone woodland. Five springs burble gently through the property, and two ponds rest in the valley below. In the spring and late summer, glorious wildflowers fill the fields with color and vibrancy. Because of its varying habitats, Nellie Hill in Dover Plains is a hot spot for migratory birds.
Ninham Mountain
The Ninham Mountain summit may be it's focal point, but this 1,023-acre park in Carmel, NY has miles of over 15 miles of trails for exploration. The trails are suitable for both hiking and biking, so it is very popular with mountain bikers who have few alternatives in the area. This park is also heavily used by hunters in season. Sachem Daniel Ninham and his Wappinger Munsee people owned this land. In 1756 refugees from various tribes joined with Daniel Ninham and the camp moved to the Housatonic Valley, then to Stockbridge, Massachusetts. Ninham tried to use the courts to get his Putnam land back, but the courts were biased and Ninham lost his case. The west side, the mountain itself, also was farmed, mostly by members of the Smalley family, which is why on old maps the mountain is called Smalleys Hill. The fire tower was built in the 1930s by the Civilian Conservation Corps.
google map of trailhead
trail map
more info on the tower
reviews
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.
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 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.
Michael Ciaiola Conservation Area
Previously known as Merritt Park (and also sometimes known as Haviland Hollow), this conservation area consists of over 800 acres and is Putnam County's largest. Wildlife abounds in this conservation area. One may see deer, turkey, bobcat, bear, along with various songbirds and small mammals. One of the most popular spots is the Great Gorge Waterfall just north of the old Merritt campsite. Bring a lunch and enjoy a picnic on one of the many flat boulders with a great view to admire.
Wonder Lake State Park
Wonder Lake State Park is a 973-acre state park in Putnam County, New York, U.S. in the Town of Kent. It was founded in 1998, and has been recently expanded by the purchase of 106 acres of open space. The state park was once the summer home of television star Elizabeth Montgomery (Samantha on Bewitched). Acquisition provides protection to the Great Swamp watershed and unique open space areas.
Macedonia Brook State Park
The 2,300-acre Macedonia Brook State Park's exciting terrain has resulted from the slow wearing down of its hard rock formation base. The Blue Trail crosses Cobble Mountain and several other peaks, offering outstanding views of the Catskills and Taconics. Numerous springs and streams add to the pleasure of hiking, camping and fishing.