Livingston Manor has that “‘cool but not trying too hard’ vibe—it’s artsy, outdoorsy, and delicious all at once,” says Lisa Karvellas, co-founder of Cedar Lakes Estate in nearby Port Jervis. She suggests grabbing local goods at Main Street Farm, a pint at Catskill Brewery, and wood-fired pizza under the string lights at The Kaatskeller.

Callicoon may be small, but it punches above its weight with a mix of heritage and fresh energy. On Sundays, I always make time for the farmers market—one of the best in the Catskills—before wandering Lower Main Street, where shops like The Farmhouse Project and Lee Hartwell Antiques sit alongside cozy spots like The Creek House Grill and Peppino’s.