Exploring Woodstock, NY: A Haven of Music, Art, and Culture

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. Woodstock 1999 took place three hours beyond this hipster town. However, 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.

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. Moreover, Van Morrison wrote “Moondance” in Woodstock, perhaps inspired by the night skies made for star-gazing and romance. Consequently, thousands of artists and dreamers have been drawn to this part of the Catskills due to the region’s natural mountain beauty and peaceful ambiance.

Where to Stay in Woodstock, NY

Vigilant about retaining its small-town character, Woodstock has managed to keep out national hotel and retail chains. It is important to note that the town doesn’t have a real hotel; instead, visitors will find motels, bungalows, inns, and B&Bs. Since summer is high season here, advance reservations are a must.

The following accommodations 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 over 50 years, Twin Gables is a guest 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 has been upgraded to resemble a hipster-minimalist haven, located right on busy Route 28. Guests can enjoy a Mexican meal just steps away at Santa Fe Woodstock, which locals seem to favor.

Shopping in Woodstock, NY

Tinker Street is filled with gift and jewelry stores, eateries, and shops where you can indulge in all your bohemian lifestyle needs. There are several places where the owners’ taste level and the merchandise are outstanding:

• Woodstock Design, Tinker Street – Features minimalist clothing for women from designers like Eileen Fisher and Joan Vass. Also available are 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 delightful store in the heart of Woodstock.
• Elena Zang Gallery – Exquisite handmade pottery, plus paintings and sculptures by local artists. Located 4 miles west of Woodstock on Route 212.
• Pegasus Footwear, 10 Mill Hill Road – This store specializes in comfortable shoes ideal for walkers, offering brands like Birkenstock, Naot, and Ecco.
• Kenco, Hurley Mountain Road and Rt. 28 – If hiking, kayaking, or other mountain activities are on your agenda, this great outdoor clothing and shoe shop is located a mile west of Kingston.
• Loominus Handwovens, Woodstock Village Green – Offers chenille scarves, stoles, jackets, throws, and dusters, often with items on sale during annual events.
• Woodstock Harley-Davidson, Route 28 – A popular spot with motorcycle enthusiasts offering a range of high-priced hogs and friendly atmosphere.

Music & Culture in Woodstock, NY

Every weekend, there’s music to be heard in Woodstock, NY, often accompanied by an art show. During the summer, theater performances abound, while fall brings the annual Woodstock Film Festival. Every spring, the Woodstock Bookfest captivates readers with author panels and more. Below are resources to learn 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 who held the Midnight Ramble on his property every weekend. Though he has passed on, the music continues with various acts rocking the barn. Please check the site for upcoming shows.
• Radio Woodstock, also known as WDST, is Woodstock’s local independent radio station broadcasting alternative rock, world music, and live programming at 100.1-FM. Visit the site to listen live.
• Woodstock Bookfest, formerly the Woodstock Writers Festival, celebrates books and writers every spring.
• The Woodstock Film Festival is an annual event held in early fall, showcasing indie talent.

Although a new generation has come to Woodstock, search no further for reiki practitioners, drumming circles, yoga lessons, journal-writing classes, and mind-body healers. Woodstock provides compelling evidence that the spirit of the Sixties — of community, sharing, spiritual awareness, personal growth, freedom, and proud eccentricity — lives on.