5 Favorite Hiking Trails Near Pawling, NY


We know many of our guests are avid hikers, whether they're completing the whole Appalachian Trail or just looking for a casual Sunday saunter. Here are five beautiful trails just a stone's throw from Station Inn.


 5 Favorite Hikes Near Pawling, NY


Appalachian Trail from the AT Train Stop (Great Swamp Boardwalk & Corbin Hill)

Easy to Moderate | 3–12 miles depending on route

Right off the Appalachian Trail stop on the Metro-North Harlem Line, this trail begins with a magical 1,600 foot boardwalk spanning the Great Swamp. Walk among the reeds then find yourself back in the trees; follow the trail long enough and it’ll lead across West Dover Road up to Cat Rocks.


Cat Rocks via the Appalachian Trail

Moderate | ~1.8 miles (short version) or 7.2 miles out-and-back from the AT train stop

Right in the parking area for this hike, you'll meet a local celebrity—the Dover Oak, the largest tree on the AT. Then, embark on a challenging but short climb with a satisfying payoff. At the top, spread out on Cat Rocks with a picnic and enjoy gorgeous views of surrounding mountains, farms, and the town of Pawling.


Pawling Nature Reserve

Easy to Moderate | Multiple trails totaling ~12 miles

The multiple trails in this 1,060-acre area will bring you through a gorge rimmed by hemlocks, swamps, overgrown fields, meadows, fern glens, and forested uplands. The tree-species guessing game along the trail is a great distraction for curious kids, as are the frogs and salamanders bubbling in spring’s vernal pools.


Dover Stone Church Preserve

Easy | ~1 mile to the cave, 4+ miles of additional trails

This enchanting trail in nearby Dover leads to a cathedral-like rock formation christened the Dover Stone Church, a fissure in metamorphic rock through which a brook flows, forming ledges and cascades which descend into a pool below. Kids and adults alike will love darting across the rocks and exploring the cavern.


Kent Falls State Park

Easy to Moderate | ~0.8–1.1 miles

Just across the Connecticut line and well worth the quick drive, Kent Falls offers a chance to wander across an old-fashioned covered bridge and feel the mist on your face as water cascades 250 feet down to the Housatonic River. Check out the charming village of Kent after the hike for lunch and shopping. Ascend the steps to see waterfall after waterfall, or head into the woods for a quieter walk.

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48 Hours in Pawling

September 25, 2026
a relaxing weekend away
Living room with dark wood furniture, blue chairs, and a large window.

Chapman House Writing Residency: Sunday November 15 - Friday November 20, 2026

September 30, 2025
This November, we are excited to offer our second annual no-cost writing residency to four writers at the Chapman House, a property of Station Inn Pawling, hosted in partnership with the Pawling Library. The dates for this year’s residency are Sunday November 15 – Friday November 20. This residency is open to emerging writers of fiction, memoir, poetry, and nonfiction. We define "emerging" to include writers who have not yet published a book-length project and do not have one forthcoming in the next year. The Chapman House has four beautiful suites set in the heart of the charming Village of Pawling. We hope the time away from routine and responsibility will provide fertile ground for creative inspiration. Write, hike on the nearby Appalachian trail, connect with the other writers, soak up small-town life, or just take time to let your brain settle and ideas germinate. We are excited to partner with the Pawling Library to host a public reading and reception featuring the residents on Thursday, November 19. The library will also provide a dedicated workspace for the residents to use for the week.