In many ways the village of Woodstock is a much different place than it was during its heyday when Hendrix and Dylan roamed, wrote, and performed around town. It is, however, still a place where artists thrive, everyone is or knows a musician, wars are protested, thoughts are openly expressed, and the rules are malleable.
On a busy day in town, the sidewalks are generally split between locals, weekenders, and "second-homers"— those who live part-time in New York City but also have a home tucked away in the Catskill woods—who all flock to the village as a safe place to let their hair down, leave their bras at home, and take in the serene natural landscapes. If there's one thing that connects the Woodstock community of locals, part-time residents, and visitors, it's the Sunday afternoon drum circle, where you'll find Manhattanites in Izod polos beating drums or shaking bells alongside long-haired Deadheads. And then there's the shopping and dining.
Woodstock's main drag—Route 212, which is half Mill Hill Road, half Tinker Street—is home to everything from head shops to fine dining; spiritual stores to designer clothing boutiques. Some have been around for decades while others are like revolving doors with seasonal shops in and out. One noteworthy store that's made a comfortable imprint on Tinker Street is the Golden Notebook, a small but thorough independent bookshop open since 1978. "I see the shop as more than just a bookstore; it's a community place," says Jacqueline Kellachan, owner since 2010. "Our mission is to bring people the books they love, to bring authors to the village and the school, and to be a physical incarnation of a place to share ideas and enjoy the pleasure of discoverability."
Mirabai of Woodstock is one of a few shops that offer an array of spiritual, religious, and inspirational books and music, in addition to crystals, peace flags, and incense. They also host workshops and other occasional live music events.
Scattered clothing boutiques are varied and generally pricey, but between each diverse store, one could find an outfit for any style and taste, from flowing gypsy woman to chic male to girl's-night-out attire. Woodstock Design offers a sophisticated line of dresses, tops, and pants, plus all the accessories to go with them; perfect for professionals, but also ideal for shop-hopping. If the line of colorful cowboy boots in one window isn't enough to draw a fashionista in, the flowing Eileen Fisher garments in the adjacent window are.
When you're ready to grab a bite or a coffee, there is no shortage of options. Several eateries are also ideal settings for celeb spotting: There have been sightings of musician John Sebastian at Yum Yum Noodle Bar, while Crazy, Sexy, Diet author and healthy-living guru Kris Carr frequents the Garden Café. The latter is an organic, vegan eatery that makes such deliciously hearty meals, you'll think twice about ever making a face at the phrase "vegan food" again. (Seriously, try the black bean burger.)
Ethnic-food lovers can taste Mediterranean fare at Joshua's, which has a laid-back java lounge-slash-bar upstairs, or Indian food at Mountain Gate. Asian cuisine can be found at Wok and Roll; its attached bar, Harmony Café, features live music six nights a week.
And just as you might expect from the "world's coolest small town," wandering off the beaten path will lead to some beautiful surprises. Just off Tinker Street on Waterfall Way you'll find the Tannery Brook's waterfall, visible from Treasure Chest Antiques. A short drive away is the Karma Triyana Dharmachakra (KTD) Tibetan Monastery, where Buddhist monks, spiritual seekers, and curious visitors can learn Buddhist teachings, meditate, participate in a workshop or retreat, and tour the facility. The building features traditional Tibetan design with modern construction techniques, offering the best in Eastern and Western design. The monastery also marks the entranceway to scenic hiking trails up Overlook Mountain, which hides the ruins of the Overlook Mountain House, with stone walls, no roof, and trees growing where grand ballrooms once stood.
In the past, no description of Woodstock would have been complete without a mention of musician Levon Helm's legendary Midnight Rambles, but at press time, since the artist's passing in April the old barn at Levon Helm Studios has been without those twangy vocals and snappy snare hits. His death hit the community hard; after his family and staff announced that Helm reached the end of his journey, local radio station 100.1 WDST played a medley of songs by The Band and the Levon Helm Band, interspersed with interviews and comments from acquaintances and bandmates—each person celebrating the life of the musician, the community member, the friend. Last year, the name most often heard around town was "Irene," and it was spoken with fear or sadness—this year it's "Levon," and it's with nostalgic tones and joyous memories.
But, speaking of Irene, after almost a year since the August 2011 hurricane sent the Esopus Creek rushing down Main Street in nearby Phoenicia, the small hamlet's row of shops, galleries, and eateries seems to have healed most of its scars.
Sweet Sue's restaurant, located at the beginning of the main strip, was hit the hardest on Main Street and underwent some swift renovations, reopening just weeks later. Sue's is best known for its praised pancakes—and for the long lines of hungry brunchers waiting for a taste of the more than 20 varieties.
Phoenicia offers the best of both worlds when it comes to shopping for items for the home. The Tender Land Home is a chic boutique offering handcrafted goods by local artisans and other trendy-yet-sophisticated wares, including tabletop accessories, candle items, and more. Mystery Spot Antiques and the General Store sell quirky gift items, plus country crafts, locally made soaps, and a variety of candies. Phoenicia even has its own theater, the STS Playhouse, home of the Shadaken Theatrical Society. Stop into Mama's Boy Café for a post show coffee and treat.
Those who prefer life in the slow lane should take a ride on the Esopus Scenic Train, which makes a stop in Phoenicia. Here you'll find the Empire State Railway Museum, which preserves the history and culture surrounding the busy Hudson Valley railroads from the 1800s to 1940s. The scenic train travels onward through the forests of Kingston and Mount Tremper, home of the Emerson Resort. According to spokesperson Tamara Murray, The Emerson is "a hidden gem" that includes spacious accommodations in both the family-friendly lodge and adults-only Inn. There is also an award-winning spa that faetures both western and Ayurvedic treatment therapies; there are three onsite eateries—The Phoenix, the Catamount Restaurant, and the Country Store Café—and the Country Store gift shop. The resort also hosts live entertainment on select evenings. The intimate Spotlight on Song series curated by musician/producer Doug Yoel is worth checking out; it features regional acts such as Lucky Peterson, Sarah Fimm, Shana Falana, and other talented singer-songwriters.
And as a treat for the younger set—or the young at heart—visit the World's Largest Kaleidoscope, housed on the premises in a transformed silo. Call it a night and stay in one of the resort's sophisticated rooms, or if you're in the mood for something funkier, try Kate's Lazy Meadow not far away. Owned by Kate Pierson of the B-52s, the Lazy Meadow allows you to stay in one of nine brilliantly retro suites.