A New York Locale Once Named 'America's Coolest Small Town' Boasts A Walkable Downtown And Fairytale Charm

Victorian storefronts hold more stories than their century-old bricks let on. In Owego, the 19th-century architecture line the streets like old friends who never moved away, weathering more than a century of New York winters, housing bookshops where readers settle into worn armchairs and antique stores where treasure hunters spend entire afternoons. The Susquehanna River flows past downtown, indifferent to the accolades that have found this small town over the years, including Budget Travel readers naming it America's Coolest Small Town in 2009.

The title still rings true over a decade later. Owego sits in the broader constellation of New York's hidden gems, sharing the state with the castle-dotted waterways of the Thousand Islands region, where old-world villages offer their own hidden escapes. But Owego has carved out its own identity along the Susquehanna, with a satisfying heft of independent merchants that have built a downtown that rewards wandering.

Fortunately, there are plenty of ways to get to this fairytale town, no matter where you're coming from. A 3.5-hour drive from either New York City or Philadelphia gets you to Owego. You're also close enough to Canada that you can reach the Toronto area in about 5 hours from here. Prefer to fly? It's only 27 miles away from the domestic Greater Binghamton Airport (BGM).

Start early at Early Owego Antique Center, housed in what used to be the J.J. Newberry Building. Over 95 vendor booths fill the space here, a kind of ephemera that sends collectors into quiet raptures. It could easily consume an entire morning if you let it and still miss half of what's crammed into the showcases, but the trouble is that Owego has a laundry list of other places vying for your attention.

The Riverwalk's paths alone teem with shops and restaurants. Along Front Street, stop by The Cellar Restaurant & Lounge and settle onto one of the velvet-dark booths lining the interiors, lit with an amber glow that turns every glass of water into something that looks suspiciously like champagne. After lunch, walk to Riverow Bookshop, just across the street, an iconic establishment with its cheery yellow building, announcing itself with "BOOKS" painted across the façade. The staff will pour you tea or wine while you browse on creaky hardwood floors. What more can you ask for?

The answer lies a 2-minute walk away in the aptly named Spellbound Books for this equally spellbinding little town. It looks more inconspicuous from the outside, with just a welcome mat and a chalkboard advertising weekend soup specials. But it's a different world entirely once you step inside, like discovering a Hobbit door into someone's very specific dream of what a bookstore should be. It leans hard into its folk and fairytale theme, while doubling as a cafe that serves locally roasted coffee and bagels. Choose the barista-favorite mocha pistachio latte to truly clinch the deal. Along with everything else conspiring to make you fall in love with the place, Spellbound Books commits to its concept with workshops that include, delightfully, potion making.

Indeed, with so much ground to cover, it only makes sense to stay a few days to make the most out of it. The accommodations are destinations in themselves, well worth the extra time, too. Take the Belva Lockwood Inn, an adults-only bed and breakfast that operates out of the restored home of Belva Lockwood herself. She ran for president twice in the 1880s before women could even vote, and became the first woman to argue a case before the Supreme Court. Staying here means experiencing that same defiant spirit, right down to the tunnel system beneath the building, believed to have been part of the Underground Railroad. You're greeted with a complimentary drink at the piano bar — crafted from an actual piano with ivory keys preserved under glass — and rooms decorated with a meticulous level of period detail to transport you to another time. Breakfast arrives in a picnic basket delivered to your door each morning, which beats a continental buffet in a fluorescent-lit lobby by several miles.

If the idea of staying in a historical figure's former home feels too intimate, Tioga Downs Casino Resort is just a short drive away from town and offers a wildly different vibe. The place operates as a working harness racetrack from May through September, but for the rest of the year, the casino takes over, featuring nearly 900 slot machines, 28 table games, and a poker room. On-site restaurants offer everything from quick bites to full dinners at P.J. Clarke's, the New York steakhouse that has been operating since 1884. It's a useful contrast if you've already maxed out on Victorian appeal for the day, especially in a region that overflows with charming storybook towns, wine, and waterfront escapes.