The Appalachian Trail is one of Dutchess County’s largest park with 30+ miles of trails within a protective corridor of 4,000+ acres.
The trail enters via Southern Dutchess County (north end of Fahnestock State Park) through the towns of East Fishkill, Beekman, Pawling, and Dover before entering Connecticut.
There is Free Parking in Pawling, NY off Route 22. The free parking is located at Pawling's Metro-North Appalachian Trail Train Station
The Pawling Appalachian Trail has a new 1,600 foot long boardwalk spanning the Great Swamp. The boardwalk provides several sitting areas and a 34-foot bridge that provides easy access to and from the Metro-North AT train station. Crossing the Great Swamp was originally not a problem for hikers, but storms and beaver dams constructed created many problems weekend hikers. Raised water levels interfered with traditional trail-maintenance techniques, and a temporary solution was improvised using cinder blocks, wood pallets and planks until the boardwalk's completion.
Hike Pawling Appalachian Trail Starting Points
#1 From Metro-North AT Train Station on Route 22 to Cat Rocks Out and Back is 7.2 miles. Walk the new boardwalk, climb Corbin Hill, descend through wet meadow to West Dover Road at the large Oak Tree, continue south on AT; side trip along the way to Telephone Pioneers Shelter and reach Cat Rocks with it’s wonderful viewpoint.
#2 Appalachian Trail Route 22 through Pawling Nature Preserve.
Approximately 5 miles. The trail rises through meadow, over stiles, to the Hammersley Ridge bordering the Harlem Valley. Enter the Pawling Nature Preserve woodland area onto the red trail in order to return, and again hit the AT southbound.
#3 Dover Oak to Route 22, 3.2 miles oneway. Need Two Cars
Ideal weekend hiking for beginners. Car pool from route 22 Metro-North Appalachian Trail train station to the Big Oak Tree on Dover Road in Pawling.
Start hike at large Dover Road Oak Tree - simple uphills through meadow, (say hello to the cows) then tip=toe on boards through wet meadows, uphill then downhill woodland onto flat "Great Swamp" which is where the new boardwalk is located. The new Appalachian Trail boardwalk has several areas with benches. (Midway, view swampy area with beaver dams). Plan on an hour and a half walk with shuttle to retrieve cars. 150 feet north of Metro-North Appalachian Train Station is a garden center with some food, water and showers. Sprint cellphones work OK
How to get to the Appalachian Trail by train from New York City.
Go to New York City Grand Central Terminal off 42nd Street by Vanderbilt or Lexington Avenue. Pawling, NY is approximately 80 miles north of New York City.
Weekdays: Take the Harlem Line train to the Pawling, NY train station. You will need to hop onto a taxi for about a 10 minute ride to route 22. On the way back, use your right thumb and catch a southbound car heading into town.
Weekends: Take the Harlem Line train directly to the Appalachian Trail train station. Train leaves from Grand Central Terminal Saturday, Sunday and holidays only.
By Geoffrey Gonzalez Dutchess County hiking trails.