7 Reasons to Drive to Woodstock, New York
The small Catskills town is more than its music festival past.
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, New York, fall to the back of Empire Staters’ minds. But that’s no excuse for leaving the scenic road to Ulster County untraveled.
To assume that Woodstock is only notable for its namesake 1969 music festival would be a major blunder—the festivities weren’t even held within city limits. 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, or entire week, the 2-hour drive from NYC 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 seven reasons why the journey to Woodstock won’t disappoint.
See how an artists’ colony rose to the 21st century
In the late 1800s, artist colonies began popping up in Western civilization as small rural communities where like-minded crafters could separate from urbanization and work on their trades together. The Byrdcliffe Arts Colony near Woodstock was one of those early utopian communities, comprised of seven farms, 1,500 acres, and 30 buildings at the time of its completion in 1903. There, artists practiced nearly every trade imaginable—furniture-making, metalworking, pottery, weaving, painting, you name it.
Today, the Woodstock Byrdcliffe Guild continues to attract artists hoping to retreat from city life and hone their craft. Visitors can tour the grounds and see where magic was made, then stop by the Woodstock Artists Cemetery in town to pay respect to the creatives in Woodstock who died doing what they loved.
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 ‘60s-era alt movie theater Tinker Street Cinema, educational Woodstock Artists Association & Museum, and quaint Woodstock Public Library will satisfy.
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, meatballs from Sharkie’s, sandwiches from Sunfrost Farms, acai bowls from Little Apple Cafe, cocktails from Station Bar & Curio, organic food from Oriole 9, and ice cream from Sweet Dreams Organic with a confection from Peace, Love & Cupcakes to top it off.
Clock some R&R at a quaint local inn
Cute towns naturally come with cute places to stay. While the options are plentiful in Woodstock, a few low-capacity inns and hotels rise above the competition. The historic Twin Gables Guest House was built in the 1880s and established as a hotel during the boom of Woodstock’s artist colony. Its charming aesthetic fits right in on Tinker Street, with a quaint exterior, fashion-forward decor, and the choice of a private suite or community living.
For a woodsier experience, choose between the Woodstock Way Hotel and the Woodstock Inn on the Millstream. The former could be described as cabin chic, harboring modern upscale rooms behind a waterfall just off Tinker Street—plus, its communal area serves La Colombe coffee and features an artisan retail space with local goods. The latter inn leans into the small-town feel, with cottages, guest rooms, and a tiny house on the grounds surrounded by gardens, lawns, and the namesake millstream.
If you don’t mind staying off the beaten path, Hotel Dylan is worth the short drive into town. The bohemian-style destination has 22 rooms that look out on fire pits in the central lawn. Visitors can borrow board games and vinyls from the front desk—there’s a record player in every room —and enjoy its saltwater pool during warmer months.
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.
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. The park is most famous for its land art, in which the creator turned the walls of an abandoned quarry into a 6.5-acre stone sculpture inspired by Mayan ruins.
The park as a whole spans 50 acres that includes stunning meadows and forest paths, and rotating art galleries mean there are always new sculptures to see.
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.
Wind down at a Tibetan Buddhist monastery
Overlooking Woodstock is Karma Triyana Dharmachakra, or KTD, a Tibetan Buddhist monastery that serves as the North American seat for the head of the Karma Kagyu lineage. There, people can sign up for multi-day personal retreats or stop by on weekdays for public tours.
When the Karma Kagyu leader decided to open the lineage’s first US monastery, he wrote that “all indications seemed to be that this must be the place, the most auspicious and appropriate place for the construction of the monastery,” adding that his goal was not just to erect a building, but to use the grounds to contribute to the peace and harmony of Americans.
Don’t have time for it all? Looks like a second trip to Woodstock is in store.