In a state that’s home to the Hamptons, Finger Lakes, Appalachian Trail, and Big Apple it’s no surprise that small communities like Woodstock, fall to the back of the mind. To assume that Woodstock is only notable for its namesake 1969 music festival (that didn’t occur there) would be a major blunder—the three-day festival was held on a dairy farm in nearby Bethel. In reality, Woodstock is a charming little Catskills oasis where fewer than 6,000 residents prop up an art, religion, music, and theater scene worthy of national attention.
Whether you’re visiting for a day, weekend, entire week, or longer, the drive to Woodstock will prove worth it. If you have some extra time to kill, the town can also be reached by transit—just head to Poughkeepsie via Metro-North or Amtrak then use the Ulster County bus service to get to Kingston Plaza and then Woodstock.
Still need convincing? Here are five reasons why the journey to Woodstock won’t disappoint.
1. See how an artists’ colony rose to the 21st century
In the winter of 1902, construction of the Byrdcliffe Arts Colony began on Mount Guardian just outside of Woodstock. Seven farms, 1500 acres in all, were purchased for the enterprise by a wealthy Englishman named Ralph Radcliffe Whitehead. By the time it was completed in 1903, 30 buildings stood comprising what has been referred to as a textbook example of a utopian Arts and Crafts community.
The Arts and Crafts movement began in England in the last quarter of the 19th century as a reaction against rapid urbanization and industrialization. It’s most passionate and well-known English spokesmen were art critic, John Ruskin and artist, William Morris. They shared a rural, utopian ideal based on a brotherhood of artistic collaboration. They believed that life would have enhanced meaning if work reflected the nobility thought to have been lost when machines eliminated the need for the skills and art of hand craftsmanship.
Today, the Woodstock Byrdcliffe Guild continues to attract artists hoping to retreat from city life and hone their craft. Visitors can tour the 250-acre mountainside campus grounds and see where magic was made then stop by one of Woodstock’s most enduring settings, the Woodstock Artists Cemetery.
2. Stop, shop, and eat on Tinker Street
Every small town has a main street and in Woodstock, it’s Tinker Street. If you’re looking for a pastime, the 1960s-era alt movie theater Tinker Street Cinema, educational Woodstock Artists Association & Museum (WAAM), and quaint Woodstock Public Library will satisfy.
Since its founding in 1919, WAAM has been committed to exhibiting, collecting, and supporting artists and art education and in sustaining the tradition of Woodstock as a Colony of the Arts. Located in the center of the village of Woodstock, WAAM functions as a cultural center as well as a repository for the work of American artists associated with the Art Colony.
If you want to support small business, there is no shortage of gift shops, boutiques, and assorted retail stores. Get a book to read in nature at The Golden Notebook, a vacation keepsake at The Rare Bear, a vintage find at Three Turtle Doves, and a handmade candle at Candlestock on Tinker’s sister street Mill Hill Road— or just roam the downtown and see which window boxes call your name.
And when you get hungry from all your Woodstock adventures, treat yourself to local grub: tacos from Tinker Taco Lab, brisket from Dixon Roadside, hot meatball dishes from Sharkie’s, salads and sandwiches from Sunfrost Farms, açaí and smoothie bowls from Little Apple Cafe, cocktails from Station Bar & Curio, locally sourced organic food from Oriole 9, and ice cream from Sweet Dreams Organic with baked goods from award-winning Peace, Love & Cupcakes to top it off.
3. Embrace the small town’s music and theater
While you’re in the area, you can (and should!) visit the iconic Woodstock Festival grounds in nearby Bethel, New York—just keep in mind that the area’s music and theater festivals far predate 1969. In the same way that the town’s culture was built on physical arts and crafts, the community has long valued performance art as a valuable form of expression and entertainment. At The Maverick, home to a barn-like concert hall that’s still in operation today, locals have been enjoying outdoor hippie music festivals since the dawn of the 20th century.
In the decades that followed, the music and theater scene exploded to include now-prominent spots like the Woodstock Playhouse, a rural extension of Broadway, and the Levon Helm Studios and Bearsville Theater which host a variety of shows.
From May to September, the city also hosts outdoor concerts at the Village Green for all to enjoy.
4. Roam through a renowned sculpture park
East of Woodstock sits the Opus 40 Sculpture Park and Museum—aptly named, since it’s arguably the region’s most impressive feat. Created over 37 years by pioneering artist and professor Harvey Fite, Opus 40 is a nonprofit sculpture park, museum, and artistic environment with 63 acres of meadows, historic quarrying trails, and bluestone quarries—centered on 6.5 acres of earthwork sculpture.
Fite hand-sculpted Opus 40 entirely from bluestone harvested on site, fusing the local quarrying and ancient Mayan and Aztec stonework learned through his travels. He framed his stonework sculpture with the surrounding woods and mountains, ensuring the local ecosystem would always be central to this Natural Historic Register site. An artisanal studio/home overlooking the sculpture created by Fite in the late 1930s and a series of freestanding bluestone sculptures and fountains complete the large artistic environment at the center of our site.
Guests can experience the site for day-visits, guided tours, classes and workshops, or a live performance.
5. Take in the scenic Catskills landscape
You don’t need to go out of your way in Woodstock to appreciate the natural beauty of Catskill Park but if scenery is a priority you can immerse yourself in the environment through a number of hiking trails and lookout points.
The obvious nature destination is the Overlook Mountain Wild Forest—the 4.6-mile mountain trail begins beside the monastery and runs along ruins of a never-completed hotel, a historic fire tower, and stunning viewpoints of the Hudson Valley.
Other nearby activities include hiking the 1.3-mile Sloan Gorge Loop which features vernal pools and unique rock formations and passing through Woodstock Waterfall Park in the heart of town, a small community area fit for people of all ages.
Don’t have time for it all? Looks like a second trip to Woodstock is in store!
Don’t bother Max’s cows. Let them moo in peace.
—Sign in the town of Wallkill protesting the festival held on Max Yasgur’s dairy farm, as reported in the New York Times, August 16, 1969