Overlook Mountain above Woodstock in early fall. Photo by Daniel Case, CC BY-SA 4.0, via Wikimedia Commons; color-graded.
The most famous thing about Woodstock never happened here. The 1969 festival that made the name a household word took place on a dairy farm in Bethel, some sixty miles to the southwest. Woodstock lent it the name, and the reputation that came with it, because by then the town had already spent nearly seventy years as one of the most creative small places in America. Painters arrived first, at the turn of the twentieth century. Musicians followed, and over the decades so did writers, potters and a steady stream of people from the city looking for something they couldn’t quite name. Many of them found it.
The best things to do in Woodstock, NY still trace back to that history: a working arts colony founded in 1902, a summer chamber music series that has played every season since 1916, a mountain with a ruined hotel on top, and a main street lined with independent restaurants, galleries and shops. Here is how to spend a weekend in the town that gave a generation its name.
Getting Your Bearings in Woodstock
Woodstock sits at the foot of the Catskills, about two hours north of New York City and fifteen minutes west of Kingston and the Thruway. The town center is compact. Tinker Street and Mill Hill Road meet at the village green, and most of what this guide covers sits along those two streets or a short drive up into the hills around them. Bearsville, a hamlet just to the west, holds a few of the town’s best-known music venues.
Parking in the center is mostly metered lots and street spaces, and on a summer Saturday they fill early. Arrive in the morning, park once, and walk. The town rewards it.
Landmarks Worth the Trip
Byrdcliffe is where modern Woodstock began. Ralph Radcliffe Whitehead founded the arts colony in 1902 on the slopes above town, and it remains one of the oldest continuously operating arts colonies in the country. Today the Woodstock Byrdcliffe Guild runs exhibitions, artist residencies and performances at the Byrdcliffe Theater, and the hillside campus of rustic studios is worth a walk on its own.
Where to Eat
Woodstock eats well for a town of its size, and its restaurants have as much personality as its history. Here is where to go, depending on the kind of meal you’re after.
SILVIA on Mill Hill Road is the one most visitors have already heard about, and it lives up to the buzz. It’s a warm, wood-fired New American restaurant with a buzzing bar, good music and a menu built for sharing: house pita with whipped butter, smoked beets, prosciutto with fig and a mushroom pasta people plan return trips around. Book it for a special dinner, or grab a seat at the bar. For something easygoing, Pearl Moon a few doors down is a lively all-day spot with live music, a dog-friendly patio and a brunch menu that runs from birria tacos to crab cake Benedict.
The Garden Cafe is a sunny, welcoming vegetarian and vegan cafe with a garden patio, where the tofu satay, veggie lasagna and soup-and-cornbread lunches win over plenty of people who eat meat at home. Alba’s Kitchen on Tinker Street is a cozy, art-filled house turned restaurant with a menu that wanders happily from Salvadoran pupusas and huevos rancheros to pizza and clam linguine, the kind of small, personal place locals have been quietly loyal to since it opened.
Shelter on Mill Hill Road is the place for a fun night out with friends, with moody lighting, good music, a patio and a menu of empanadas, milanesa, skirt steak and smash burgers meant for passing around the table. At the far end of Tinker Street, Tibet Pho serves Tibetan dumplings and Vietnamese pho beside the creek, a relaxed, warm-hearted spot where the momos and lemongrass chicken are reason enough to walk the extra block.
Coffee and Bakeries
Bread Alone is a Catskills institution, an organic bakery that got its start just down Route 28 in Boiceville, and on weekend mornings the line at its Woodstock cafe on Mill Hill Road is part of the ritual. It moves quickly, and the reward is a pistachio latte, a canelé or an egg sandwich on bread that is the whole point. Up on Tinker Street, Overlook Bakery is the stop after a hike: chocolate chip cookies people call addictive, rich layer cakes and plenty of vegan and gluten-free options.
For a morning bagel, Moonrise Bagels is known for its playful stuffed bagels, from buffalo chicken to Reuben, and has built a following on Tinker Street. And Nana’s Take Out Cafe & Sweetery on Mill Hill Road is a sweet little cafe with a friendly counter, hearty breakfast sandwiches and a case of homemade cakes for the drive home.
Where to Drink, and Where to Hear Music
In Woodstock, the bar and the stage are often the same room. Colony fills a 1929 building with an intimate music hall, an upstairs balcony that looks right down on the stage, and a beer garden out back, and it books shows most nights. Small Talk is the opposite kind of night: a tiny, cozy cocktail bar at the foot of Tinker Street, unassuming on the outside, where knowledgeable bartenders talk you through inventive drinks. It’s perfect before dinner or after a show.
Out in Bearsville, the newly renovated Bearsville Theater is a two-level room beside a stream with excellent acoustics, a small enough space that every seat feels close. Nearby, Levon Helm Studios carries on the Midnight Ramble, the barn concerts the late Levon Helm of The Band started at his home studio. The barn sits deep in the woods, the sound is warm and close, and some fans stand right behind the musicians. For music lovers, it’s about as close to the Woodstock legend as a visitor can get.
Every summer, Maverick Concerts presents chamber music on summer weekends in a rustic concert hall built by hand in the woods, a series that has run every summer since 1916. Sitting under the old wooden beams with the windows open to the trees is a uniquely peaceful way to hear music. The Woodstock Playhouse rounds out the stage scene with a summer season of musicals, tribute concerts and shows for kids that make it an easy family night out. For craft beer, Woodstock Brewing runs a friendly brewery and beer garden about twenty minutes west on Route 28 in Phoenicia, with fire pits, mountain views and plenty of room for families and groups.
Art and Culture
The Woodstock Artists Association & Museum, founded by the town’s artists in 1919, sits on Tinker Street across from the green and shows both its historic collection and contemporary work by regional artists. Around it, small galleries line Tinker Street and Mill Hill Road, and the Historical Society of Woodstock tells the longer story of how a mountain farm town became an art colony.
Outdoors: Overlook Mountain and Beyond
Overlook Mountain is Woodstock’s signature hike. From the trailhead on Meads Mountain Road, a few minutes’ drive up from the village green, a wide old carriage road climbs steadily for about two and a half miles to the summit. Near the top, the trail passes the roofless shell of the Overlook Mountain House, the last of several grand hotels built on the peak, never finished and slowly being reclaimed by the forest. Push on to the fire tower and the view opens across the Hudson Valley, the river and the Ashokan Reservoir. It’s a steady climb on a wide old carriage road, manageable for families with older kids, and the payoff at the top is one of the great views in the Catskills.
For a gentler outing, the Ashokan Reservoir is about fifteen minutes away, with a flat promenade along the water and wide views of the Catskill peaks.
Farms and Seasonal Stops
The Woodstock Farm Festival runs a weekly farmers’ market through the growing season, with local produce, baked goods and prepared food, and it doubles as one of the town’s best people-watching hours.
More Things to Do in Woodstock
The Golden Notebook on Tinker Street is a small, cozy independent bookstore stuffed to the rafters, with a well-chosen kids’ section and signed copies worth hunting for. On weekends in season, Mower’s Saturday & Sunday Flea Market fills a field just off the village with vintage finds, records, art and odds and ends, and it has been a Woodstock fixture for decades. And about twenty minutes northeast in Saugerties, Opus 40 is a six-and-a-half-acre sculpture of quarried bluestone that one artist spent nearly four decades building by hand.
When to Visit, and Where to Stay
Summer is Woodstock at full volume, with Maverick concerts, the farm market and Tinker Street at its busiest. Fall brings the foliage and the best hiking weather on Overlook. Winter is quiet in the best way, with music in small rooms and a table at SILVIA that is actually possible to get.
Woodstock pairs naturally with the rest of the region. Kingston is fifteen minutes east, and our field guide to Beacon covers another Hudson Valley town with art at its center. When you’re ready to plan a longer stay, browse Artisan Stays homes in the Hudson Valley and Catskills.
Stay Nearby
