Woodstock in NY's Catskill Mountains

Weekending in Woodstock, Two Hours from New York City

Catskill Reservoir, Woodstock, New York
Catskill Reservoir, Woodstock, New York.

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It never happened in Woodstock in 1969: The Big Concert took place in Bethel, New York, 50 miles to the south. Woodstock's 25th-year reunion was held in Saugerties, miles to the east. And Woodstock 1999 took place three hours beyond this hipster town.

Yet for nearly 50 years, the town of Woodstock -- a leafy hamlet two hours' drive from New York City -- has been synonymous with music, summer, creativity, and hedonism.

Woodstock Photo Gallery >

Bob Dylan, in his heyday, holed up in Woodstock and collaborated with The Band to create the album "Music from Big Pink," named after a nondescript local house. Van Morrison wrote "Moondance" in Woodstock, perhaps inspired by the night skies made for star-gazing and romance. And thousands of artists and dreamers have been drawn to this part of the Catskills by the region's natural mountain beauty/font and peaceful, easy feeling.

Where to Stay in Woodstock, NY

Vigilant about retaining its small-town character (don't count on your cell phone to deliver unbroken coverage here; locals object to defacing the landscape with relay towers), Woodstock has managed to keep out national hotel and retail chains.

In fact, the town doesn't have a real hotel. What it does have are motels, bungalows, inns, and B&Bs. Since summer is high season here, advance reservations are a must.

The first two of the following are within walking distance of the town's central Village Green. (Travelers without a car can reach Woodstock via Adirondack Trailways buses that leave the Port Authority terminal in New York City and stop across from the Village Green.)

  • A restored 1940's motel, The Woodstock Inn on the Millstream at 38 Tannery Brook Road stands by a classic Catskills swimming hole, perfect for cooling off. Continental breakfast is served in a small sun room. On the day we visited, a group of musicians rehearsing for that night's in-town gig filled the air with gentle sounds.
  • Located at 73 Tinker Street (Woodstock's main thoroughfare) for more than 50 years, Twin Gables is a guest home -- a private home with extra baths and bedrooms. Nine bedrooms, decorated with period furnishings and original art, are maintained for visitors. Kids are accommodated at the owners' discretion.
  • You'll need a car to reach 10-room Hotel Dylan, the newest digs in town. This former motel, upgraded to resemble a hipster-minimalist haven, is located right on busy Route 28, so you'll have to go into town to catch the country feeling. Or roll out of bed for a Mexican meal, just steps away at Santa Fe Woodstock, which the locals seem to like. 

Shopping in Woodstock, NY

Tinker Street is filled with gift and jewelry stores, places to eat, and shops where you can stock up on all your bohemian-lifestyle needs: obscure music, "healing" crystals, St. John's Wort bubble bath, and tie-dyed apparel. There are also several places where the owners' taste level and the merchandise are outstanding:

  • Woodstock Design, Tinker Street - Features minimalist clothing for women from designers who include Eileen Fisher and Joan Vass. Also shoes by Donald J. Pliner, Arche and Santana.
  • Jean Turmo, 11 Tinker Street - Fabulous fragrances for the bath, and other sensual delights are found in this sweet-smelling store in the middle of Woodstock.
  • Elena Zang Gallery - Exquisite handmade pottery, plus paintings and sculpture by local artists. Located 4 miles west of Woodstock on Route 212.
  • Pegasus Footwear, 10 Mill Hill Road - If you're a walker, this store is a real find. Dedicated to selling comfortable shoes, it carries Birkenstock, Naot, Ecco, and other brands that make toes curl up and smile.
  • Kenco, Hurley Mountain Road and Rt. 28 - If you're planning to do any hiking, kayaking or other mountain activities, you can outfit yourselves at this great outdoor clothing and shoes a mile west of Kingston.
  • Loominus Handwovens, Woodstock Village Green -- Yummy chenille scarves, stoles, jackets, throws, and dusters. ( In addition to annual July and December sales, there are often items on sale.)
  • Woodstock Harley-Davidson, Route 28 - Okay, so more than a few of the customers closely resemble Hell's Grandpas, scraggly gray ponytails and all. But they're still having a kick-ass time on their high-priced hogs.
2016 Woodstock Film Festival - 'Blind' Premiere
Simon Russell /Getty Images

Music & Culture in Woodstock, NY

Every weekend, there's music to be heart in Woodstock, NY and usually an art show to boot. During the summer, the play's the thing. Fall brings the annual Woodstock Film Festival. And every spring the Woodstock Bookfest thrills readers with author panels and more. These resources can lead you find out more about current events:

  • The Woodstock Chamber of Commerce provides information on dining, music, and more.
  • Levon Helm, a former member of The Band, was a Woodstock hero. Every weekend he held the Midnight Ramble on his property. Although Levon has passed on, the music continues. Different acts, both well-known and not, rock the roof of the barn. Check the site for upcoming shows.
  • R​adio Woodstock, aka WDST, Woodstock's local independent radio station, broadcasts alternative rock, world music, talk, blues, and live programming at 100.1-FM. Visit the site to hear it live.
  • Woodstock Bookfest, formerly the Woodstock Writers Festival, celebrates books and the people who write them every spring.
  • The Woodstock Film Festival is an annual event held in the early fall that draws indie talent.

Although a new generation has come to Woodstock, you still won't need to search far for reiki practitioners, drumming circles, yoga lessons, journal-writing classes, and mind-body healers. Woodstock provides conclusive evidence that the spirit of the Sixties -- of community, of sharing, of spiritual awareness, of personal growth and freedom, and of proud eccentricity, lives on.

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