Woodstock is where artistic legacy and mountain beauty meet
When people think of Woodstock, the iconic 1969 festival comes to mind, even though it was held about 60 miles away in Bethel, New York. Today, this small mountain town still attracts tourists wearing tie-dye T-shirts and flowy skirts, but Woodstock is more than just a tourist destination. “Woodstock continues to be the most dynamic and energetic destination in the Hudson Valley,” says Sean Zimmerman, associate broker at Halter Associates Realty Inc., who has been helping homeowners sell their homes for over 20 years. “We have more restaurants, music venues, art galleries and shops than any other town in the region by a long shot. I moved away when I was younger, but it’s the nature that drew me back in.”
Tucked away in the Catskills, the town’s scenic landscape draws artists nationwide. Woodstock’s art scene dates to the founding of the Byrdcliffe Arts Colony and Maverick Art Colony at the turn of the 20th century. “My grandmother lived in the Maverick colony, and my grandfather was an author,” says Laurie Ylvisaker, associate broker at Coldwell Banker Village Green Realty, who has been in the industry for nearly 40 years. “In order to raise money for a new well, they started the Maverick Festival every summer, and it was riotous. It was essentially the original Woodstock.” Over a century later, the festival still occurs at Maverick Concert Hall.
In-town homes are on walkable streets near art, music and dining
In the town of Woodstock, residential streets with modest lots fan out from Route 212. Home styles include American Foursquares, cottages, split-levels, Tudor- and ranch-style homes. Due to its proximity to the village, prices range from the upper $400,000s to over $1 million. Contemporary buildings with black siding and large windows are a newer trend, while the occasional historic Queen Anne and Victorian farmhouse are scattered in between. “Some homes can still sell for as low as $300,000 in Woodstock, but if you want an idyllic retreat, prices begin in the $700,000s and go up from there,” Zimmerman says. Rural mountain roads lead to various secluded estates on acres of land. Custom-built homes and modern log cabins with breathtaking landscapes can range from the upper $900,000s to over $4 million. On the outskirts of town, ranch-style homes can sell for under $300,000. Prospective homebuyers can also build their dream home, with plots of land selling from $10,000 for 1 acre close to town to $7 million for over 600 acres.
Children learn at well-rated schools, some with a Buddhist influence
The Onteora Central School District serves the Woodstock community and earns a B-plus rating from Niche. Kindergarten through third graders may attend Woodstock Elementary, scoring an A-minus, and fourth through sixth graders may attend Bennett Elementary, scoring a B. Onteora Middle earns a B-plus, and Onteora High receives an A-minus. Alternative schools are also popular amongst residents, including Woodstock Day School and the Middle Way School. Both are rooted in Buddhism and emphasize holistic learning, nature and interpersonal skills.
Woodstock has hiking trails, swimming holes and parks in the Catskills
Wooded mountain roads wind around Woodstock while the Saw Kill River’s flowing waters weave in between. The river gives way to calm pools of water, making it a popular spot for a quick dip during the summer. “There are numerous secret and not-so-secret swimming holes like Big Deep and Little Deep,” Zimmerman says. Big Deep is just one mile from the village along New York Route 212, and Little Deep is less than a mile farther along West Hurley-Zena Road.
Heading west into Woodstock, golfers can hit the range at the Woodstock Golf Club, a member-only course. Pocket parks like Village Green and Waterfall Park are scattered throughout the heart of town. Continuing west, glimpses of The Comeau Property, Woodstock’s largest public park, peak through tree-lined streets. The property spans 76 acres and is home to multiple sports fields, hiking trails along the Sawkill stream and a small stage for the community’s annual Shakespeare Festival.
On the outskirts of the village, hiking trails snake around the Catskills. “Overlook Mountain is a crowd favorite,” Zimmerman says. “It’s one of the most visited natural features in the region.” About a 2-mile hike leads to the Overlook Fire Tower, which offers hikers panoramic mountain views.
Tinker Street has boutiques, bookstores and restaurants
Tinker Street is lined with eclectic boutiques dotted with peace signs that sell Woodstock ’69 merch that attract tourists looking for a glimpse of the past. Bookstores feature publications that cater to the spiritually inclined, discussing mindfulness, meditation and herbal remedies. Yoga studios, wellness stores and the occasional psychic draw visitors and locals with enticing storefronts. “The yoga community and natural medicine are big around here,” Ylvisaker says. “I started doing acupuncture last year, and my life changed in two sessions.” Sunflower Market is a natural foods store that sells organic products along Route 212. A wellness information desk even helps shoppers decipher between the many supplements in stock. Hannaford is about 3 miles south along West Hurley Road for chain grocers.
Eateries range far and wide, but one commonality is their penchant for farm-to-table cuisine. “Silvia and Good Night are undoubtedly the two best restaurants in town and my favorites,” Ylvisaker says. Silvia’s dark, cozy interior offers a perfect ambiance for romantic date nights, while upscale American fare like oysters and smoked trout pate cater to those with a gourmet palate. Good Night features a softer, retro interior and Asian-inspired eats like Korean fried chicken and miso Caesar salad. Pearl Moon is one of the many casual spots around with regular live music, but ironically, this music-loving town recently passed a 10 p.m. noise ordinance.
Local theater and music celebrate Woodstock’s legacy
“Artists would come up to Woodstock since it was 2 hours from the city in the Catskills, and the environment was open to eccentricities,” Ylvisaker says. Along New York State Route 212, Woodstock Playhouse is an iconic theater that hosts a range of plays, concerts and musicals. About 2 miles west, the Bearsville Theater and its founder Albert Grossman were major players in the 1960s music revolution. Famous artists like Bob Dylan, Janis Joplin and Johnny Cash recorded in its studio. “I actually knew Janis. She was a fun gal,” Ylvisaker says. Today, its grounds hold events that range from country music festivals to fall harvest festivals and everything in between. Music seeps into the streets weekly, whether that’s the drum circle on Sunday evenings at Village Green or live performances at one of the many restaurants around town.
Scenic drives on Route 212 link Woodstock to nearby towns
Ulster County Area Transit offers free bus service throughout Woodstock, with one stop in the village and additional stops in the neighboring hamlets of Bearsville, Shady, Lake Hill and Willow. The Trailways bus also runs from the city to Woodstock. However, Woodstock is primarily a car-dependent community, and New York State Route 212 is the main thoroughfare. New York City is about a 100-mile drive along Interstate 87. Kingston is about 11 miles southeast and is also home to the HealthAlliance Hospital. Albany International Airport is about a 55-mile drive north.
Spiritual retreats at a Buddhist monastery atop Overlook Mountain
The Hudson Valley’s landscape, dotted with mountain ranges and rushing rivers, makes it popular amongst spiritual seekers. About a 3-mile drive north from the village of Woodstock, residents are greeted by colorful Tibetan prayer flags streaming along the tree line. Sitting on top of Overlook Mountain, Karma Triyana Dharmachakra (KTD) is a Buddhist Monastery and retreat center whose shrine room is enveloped in gold accents and showcases a giant golden Buddha statue.
