Earthy meets sophisticated in Woodstock, a hippie-chic Hudson Valley hotspot with a rich history.
Longtime Woodstocker Debbie Dougan has watched her famous town transform from the renowned home of sex, drugs, and rock ’n’ roll to a hippie-chic Hudson Valley hotspot that lures tourists from New York City and beyond with its earthy-meets- sophisticated vibe and rich history. But for Dougan, owner of Glo Spa (62 Ricks Rd., 845.679.7800)—a 6,000- sq.-ft. spa offering everything from facials and body treatments to massage, as well as yoga and Pilates—it’s just home. She moved there from the Bronx at age 12, and though she has spent time living in New York City, Boston, and L.A., “this is the one place I really know that I belong,” explains Dougan, who is well-versed in the town’s culture and proud of the plentiful, thriving independent small businesses. She also loves the mix of old-timers, weekend regulars, and visiting newcomers that make up her clientele. —Amy R. Partridge
Small, unique shops are a Woodstock mainstay, and Dougan is proud of the plentiful number that are women-owned, including one of her favorites— high-end vintage boutique Three Turtle Doves (62B Tinker St.).The shop offers a curated selection of Art Deco–influenced vintage jewelry, accessories, clothing, and beauty items.
For “small and understated jewelry,” Dougan makes the short trip to Rhinebeck to jeweler Adel Chefridi (47 E. Market St., 845.684.5185). “The line has always spoken to me,” she says of Chefridi’s pieces, known for showcasing gems in dotted patterns.
For wine, Dougan heads to Kingston’s The Wine Hutch (936 Rte. 28, 845.334.WINE ), another woman-owned favorite. Owner “Ursula Woinoski is incredibly knowledgeable and so likable,” Dougan says.The shop is known for its selection of local, organic, and biodynamic options.
In Woodstock’s vibrant dining scene, two favorites stand out for Dougan. These, too, are women-owned. The Garden Café (6 Old Forge Rd., 845.679.3600) is her go-to for its delicious vegan food and “simply delightful owner, Lea,” who grew up in town. Meals are organic, GMO-free, and locally sourced. The café also boasts a new juice bar. Silvia (42 Mill Hill Rd., 845.679.4242) is Dougan’s pick for special-occasion dining. The restaurant, housed in the former Joyous Lake building—a ’70s nightlife spot where the Rolling Stones, Muddy Waters, and others played—offers sophisticated New American food with Asian influences and a farm-to-table ethos in a stylish setting. “It’s a beautiful and unique spot. It’s so great to have it in the community.”
During the pandemic lockdown, Dougan and her family took to kayaking and hiking at Wilson State Park (859 Wittenberg Rd.) in Mt. Tremper.
She also recommends the Ashokan Rail Trail, a scenic 11.5-mile trail that runs along Ashokan Reservoir and is on the site of the former Ulster & Delaware Railroad corridor. It’s open to the public from sunrise to sunset year-round for hiking, biking, enjoying nature, and, in the winter, cross-country skiing and snowshoeing.
A visit to Westwind Orchard in Accord (215 Lower Whitfield Rd., 845.626.0659) is a fall must, says Dougan. You can visit a cidery, a tasting room, and an outdoor dining area offering wood-fired pizzas and live music. “There’s always something special going on there.”
Dougan is a self-professed “Christmas cuckoo,” and one of her favorite Woodstock traditions is The Sounding Joy, an annual Christmas variety show that benefits local women’s shelter the Washbourne House and is performed at Levon Helm Studios (160 Plochmann Ln., 845.679.2744). Such well-known names as Natalie Merchant of 10,000 Maniacs have performed in the show. Known as Levon’s Barn, the popular concert venue is named after its owner, the former drummer and vocalist for The Band.