This Is New York's Quirkiest Little Town
While Woodstock’s early history largely mirrors that of many other New York towns, a pivotal moment at the beginning of the 20th century forever shaped the town’s identity. In 1902, a man named Bolton Brown arrived in Woodstock on behalf of Ralph Whitehead, who was searching for the perfect location for a utopian art colony. Upon seeing the town, Brown instantly knew that Woodstock would be the right fit. After the founding of this first colony, several other colonies and art organizations emerged in the subsequent years, transforming Woodstock into the artistic and creative hub it is today. Upon browsing eclectic shops, attending a renowned theater performance, and exploring a massive stone sculpture, it quickly becomes clear why Woodstock stands out as the quirkiest town in New York.
Tinker Street
Travelers can experience a lot of Woodstock’s quirky energy along Tinker Street, the town’s Main Street. The shops in this area have all kinds of eclectic offerings, ranging from vintage collectibles to tie-died hoodies and herbal remedies. For those on the hunt for a one-of-a-kind t-shirt, Happy Life Productions is a must-visit. This graphic apparel shop has been open since 1987 and specializes in tie-dye clothing and bold graphic tees. Three Turtle Doves is another beloved shop along Tinker Street, which sells vintage handbags, accessories, and other rare finds for your closet. Woodstock High is another place to stop by if you are looking for a souvenir, selling Woodstock Memorabilia and novelty items. If you are looking for a home remedy or natural health product, Remedies Herb Shop offers a wide selection of roots, loose herbs, and spices, as well as candles, incense, and tea.
Karma Triyana Dharmachakra Tibetan Buddhist Monastery
About a seven-minute drive north of Woodstock, travelers will find the Karma Triyana Dharmachakra, a Tibetan Buddhist monastery established in the latter half of the 20th century. It was founded with the support of the Sixteenth Karmapa, in response to students seeking the presence of a Tibetan Buddhist monastery in the west. Travelers are welcome to visit the monastery any day of the week from sunrise to sunset. While exploring the grounds, the monastery recommends that visitors see the Main Shrine, the Namse Bangdzo Bookstore, and the Eight Stupas which represent the stages of the Buddha's life. Visitors can also attend a guided tour of the grounds on the weekend, with 45-minute tours available on Saturday and Sunday afternoons. The tour includes a walk through the temple, where guests will learn about the artwork, sacred shrines, and architectural features, as well as the monastery’s traditions and beliefs.
Live Entertainment & Music Scene
The Woodstock Playhouse, constructed in just 48 days, has been operating since 1938, with its first performance being Yes, My Darling Daughter. Since then, the theater has hosted countless acclaimed performances and launched the careers of many theater stars who now perform on Broadway and national tours. Some of the upcoming performances that visitors can attend include Disney’s The Little Mermaid in May, Grease in June, and Rodgers and Hammerstein’s Oklahoma! in July.
Attending a performance at Colony is also a memorable experience. Originally opened as a hotel in 1929, the venue was the tallest building in Woodstock at the time. Travelers who lodged in the hotel would often dine and listen to bands perform in Colony’s great room. Nearly a century later, guests continue to enjoy live music at Colony, with the venue hosting a performance nearly every night. The venue welcomes a diversity of performers, ranging from DJs and karaoke nights to iconic blues guitarists and folk musicians, so make sure to check the calendar to find a performance that suits your taste.
Culinary Scene
Make sure to save room for dinner, because Woodstock’s restaurants are every bit as impressive as its art and shopping scene. Travelers seeking an up-scale and contemporary meal should make reservations at SILVIA, a family-owned restaurant that uses locally sourced ingredients and cooks in an open kitchen with a wood-fired grill. Pearl Moon, meanwhile, is a great option no matter the time of day. Open for breakfast, lunch, and dinner, this restaurant serves comfort food like buttermilk biscuits, grilled cheese sandwiches, and house-made fettuccine. If you are in the mood for a post-dinner drink, head over to Tinker Street Tavern, a cozy bar set in an 1897 home that features live music from Thursday through Saturday.
Final Thoughts
Carrying more than a century of art-centered history, it is easy to see why Woodstock is such a quirky town. Meanwhile, landmarks like the Karma Triyana Dharmachakra Tibetan Buddhist Monastery also contribute to the town’s unique features, attracting visitors who want to experience a different side of New York. Even during dinner, visitors will see the creative effort that the restaurants put into meals. If you are looking for something a bit more unexpected in your travels this year, Woodstock should definitely be on your itinerary.
