This Is New York's Quirkiest Little Town
In 1902, the English-born painter Ralph Radcliffe Whitehead sent his colleague Bolton Brown into the Catskills to scout a site for a utopian arts colony. Brown settled on Woodstock, and within a year Whitehead had founded Byrdcliffe on the mountainside above town. Other colonies followed, including Hervey White's Maverick in 1905 and the Art Students League summer school in 1906, and Woodstock's reputation as an art town has held ever since. More than a century later, it still shows on the ground, in the shops along Tinker Street, in a working Tibetan monastery a few miles up the road, and in a theater built during a Depression-era summer that has been staging productions almost continuously since 1938. Woodstock has earned its reputation as one of the quirkier small towns in New York.
Tinker Street
Tinker Street carries most of Woodstock's commercial life in a few walkable blocks. The inventory runs toward the eclectic. Happy Life Productions, a graphic apparel shop that has been in the village for decades, stocks tie-dye and screen-printed tees alongside its own original designs. Three Turtle Doves trades in vintage handbags and estate finds from the mid-20th century onward. For natural remedies and apothecary goods, Remedies Herb Shop sells loose herbs, tinctures, teas, candles, and incense, along with the usual selection of crystals and cards that goes with the territory in Woodstock.
Karma Triyana Dharmachakra Tibetan Buddhist Monastery
A short drive up Meads Mountain Road northwest of the village sits Karma Triyana Dharmachakra, a Tibetan Buddhist monastery established in 1976 under the guidance of the 16th Gyalwa Karmapa as a seat of the Karma Kagyu lineage in North America. The grounds are open daily from sunrise to sunset, and the Main Shrine and the Namse Bangdzo Bookstore are both accessible without appointment. A set of eight stupas on the property represents eight formative moments in the Buddha's life. Guided tours of roughly 45 minutes run on Saturday and Sunday afternoons and cover the temple's iconography, shrines, and ritual artwork. KTD is also the North American seat of the Karmapa when he is in residence.
Live Entertainment And Music Scene
The Woodstock Playhouse has been staging productions since June 1938, when the original barn-style theater was reportedly built in 48 days and opened with a run of Yes, My Darling Daughter. The theater burned in 1988 and was rebuilt on the same site, and it now operates as a summer theater with Broadway musicals, tribute concerts, and dance programming running through the season.
The Colony opened in 1929 as the Colony Arts Hotel and was, at three stories, one of the tallest buildings in Woodstock at the time. Its ground-floor hall has been used for performances almost since it opened. Nearly a century later, Colony still hosts live shows most nights of the week, with a calendar that runs from folk and blues to singer-songwriter sets and DJ nights.
Culinary Scene
Woodstock's restaurants match the rest of the town in ambition. SILVIA, a family-run spot on Tinker Street, builds its menu around locally sourced ingredients cooked over a wood-fired grill in an open kitchen. Pearl Moon serves breakfast, lunch, and dinner, with a menu that leans toward comfort cooking in the form of buttermilk biscuits, griddle sandwiches, and house-made pastas. For a drink after dinner, Tinker Street Tavern occupies a converted historic house on the main strip and hosts live music several nights a week from spring through fall.
Woodstock
What makes Woodstock quirky is not any one feature but the combination. A 120-year-old arts colony, a Tibetan monastery on the mountainside, an 85-year-old summer theater, an apothecary, and a few dozen storefronts that each look about three-quarters committed to their own specific aesthetic all sit within a 10-minute drive of one another. For a town often reduced to a shorthand reference to a festival that didn't take place there, Woodstock has a deeper and stranger set of roots worth stopping for.
