Downtown Woodstock’s colorful boutiques and cafes encircle the Green, a patch of lawn where peace demonstrators still congregate.  Make your way to Mower’s Flea Market (Maple Lane, Saturday/Sunday 11-5pm) for one-of-a-kind vintage jewelry, album cover artwork, and antique accessories. Woodstock Bead Emporium (54 Tinker Street) stocks the most gorgeous geodes and semiprecious stones—perfect for making hippie-chic pendants.  Timbuktu (2 Tannery Brook Road) features my favorite artisan furnishings from around the globe—with a focus on sustainable and reclaimed materials, you’ll earn good karma while you shop. 



Get in touch with Mother Nature with a vigorous but rewarding hike up nearby Overlook Mountain.  The summit offers sweeping views of the Hudson Valley and Ashokan Reservoir, as well as the romantic ruins of once-grand Overlook Mountain Hotel.  Cool off with a dip in the Big Deep (Route 212 and Country Road 33) a secluded swimming hole favored by locals for its crystalline waters and sun-dappled boulders.  




For a light bite, try seasonal vegetarian favorite, Garden Café on the Green (6 Old Forge Road)—the wholesome Garden Bowl with baked tofu is earthy and savory.  The Little Bear (205 Tinker Street) is an adorable Chinese restaurant perched above the Sawkill Creek—don’t miss the delicately tender Shumai Dumplings. 



The Bearsville Theater, just next door, is legendary among music and theater enthusiasts for stellar live performances (Bob Dylan and Paul Newman once graced the stage).  Head to Robert’s Auction (43311 State Highway 28, Arkville, Saturdays at 6pm) for an unforgettable shopping experience: city and country-folk pack the auction house each Saturday to bid for a dazzling array of treasures. 



End your night with a decadent scoop of hand-churned cinnamon ice cream at Taco Juan’s (31 Tinker Street) and a stroll through Woodstock’s firefly-lit streets.  The magic of the Catskills is still in the air—I’m betting you’ll be lured back to this spot for seasons to come.