The Destination 'Where Upstate New York Begins' Hides A Secret Lake, Quaint Shops, And Appalachian Trail Access

Determining exactly where upstate New York begins can be a bit tricky and relative depending on who you ask. Just 74 miles north of New York City is Pawling, which calls itself "where Upstate begins" — serving as both a launching point into the Hudson Valley's beauty and a comforting retreat where history, community, and nature seamlessly meet. Framed by the foothills of the Berkshires, the picturesque town (with a population of 8,000 people) has a historic charm that attracts a range of travelers. Outdoor enthusiasts delight in Pawling's access to four lakes and more than 440 acres of parkland, including part of the Appalachian Trail.

Though it feels like a world away from the bustle of a major city (or even Hudson, the "Downtown of Upstate"), reaching the town is quite easy. Westchester County Airport is under an hour away, and the Metro-North Railroad has a stop right in Pawling, just two to three hours from New York City's Grand Central Terminal. This town is perfect for day-trippers, hikers, history fans, and anyone craving the upstate's bucolic calm without sacrificing accessibility. Whether you're returning to admire its landscapes or staying for the peaceful pace, Pawling is the upstate ideal of "not too far, yet a world away."

Pawling's shopping experience blends artisan charm with curated, hometown warmth. Book lovers and those who just appreciate old but amazing discoveries should make their way to the Pawling Book Cove. The independent shop features new reads alongside antique and super-rare literary finds. This is truly one of those places you can browse for hours and score something for yourself or the perfect present to bring back home for the bibliophile in your life. The establishment has been around for more than 40 years, and shoppers frequently praise the friendly and helpful staff. Located right inside the Book Cove is Pawling Antiques, a treasure chest of heirlooms just waiting to be uncovered. The space is led by a range of sellers who offer everything from postcards to crystals and home goods.

For the kids, or anyone who's still a kid at heart, Imperial Castle Toy Shop is another Pawling space where you can peruse treasures. "Hudson Valley's premiere toy shop" has the collectibles that are sure to bring back a sense of nostalgia for adults (including game consoles, board games, throwback dolls, and action figures), but also the modern toys the little ones in your family can appreciate. This is truly one of those rare shops where everyone in the family, from the youngest to oldest, can find something they cherish and turn a road trip into a vintage treasure hunt.

Pawling's shopping scene is refreshingly unhurried. It invites you to linger — chat with owners, uncover rare finds, and savor the personal touches. Every storefront echoes community pride and authenticity, making each purchase more than just a transaction, but part of a meaningful connection to the region and even something to make you remember your visit. 

While you can certainly visit Pawling and stay indoors for hours, enjoying one of Pawling's many retail options, getting outdoors and experiencing nature is also essential. The Appalachian Trail in Dutchess County contains more than 30 miles of trails and is easily accessible. There's free parking at Pawling's Metro-North station, and from there you'll be able to cross the 1,600-foot boardwalk that traverses the Great Swamp. With several seating areas and benches along the way, you'll want to marvel at all the wildlife and birds in the area. If you start at the Metro-North station, a worthwhile trail to hike is to Cat Rocks. The trail totals 7 miles out and back and includes climbing Corbin Hill, wet meadows, and ultimately Cat Rocks itself. After a moderate hike, you're rewarded with sweeping views of Pawling and neighboring Connecticut.

The Appalachian Trail is no secret (it spans 14 states and is probably the most famous hiking trail in the world), but for something that feels a bit secretive and not overrun, try Nuclear Lake. Don't let the name turn you off. Though it was once the site of a chemical explosion, the area was purchased by the National Park Service in 1979. Decades later, it's now serene, scenic, and you'll cross it before making your way to Cat Rocks. It's moderately difficult but good for beginners, and the terrain is relatively flat with a few uneven patches. Whether you venture to the "secret" lake, enjoy one of the well-traveled trails along the Appalachian, or spend a leisurely day shopping for antiques, Pawling has something for all skill sets and interests. If you find yourself enamored with Pawling, then you'll also want to check out this art trail in upstate New York.