By Carly Fisher
IG: @dinnerwithcarly
Long before Woodstock became synonymous with the free-spirited hippies and peaceniks of the Summer of Love, the famed Ulster County town was already a haven for artists, makers, quarrymen, and dreamers who shaped New York State’s creative landscape.
Drawn to the seclusion of the Catskills and the tranquility of the Ashokan Reservoir, Woodstock’s countercultural roots reach back to the early 1900s, when Englishman Ralph Radcliffe Whitehead brought the Arts and Crafts Movement to the U.S. by founding the Byrdcliffe Arts Colony in 1902. Grounded in hand craftsmanship and a reverence for nature, the region has remained a magnet for creatives ever since, nurturing generations of sustainable art and land-based practices across Ulster County.
For travelers, that legacy offers a unique opportunity to explore the art, stewardship, reclaimed spaces, and local craft that has shaped the past, present, and future of the area. Here’s how to pack in a taste of Ulster County into one weekend:
Start with the galleries at the Woodstock School of Art, located in a historic bluestone and timber building from 1939, where you can browse exhibitions from local artists or sign up for a weekend drawing, painting, printmaking, or sculpture workshop.
Then wander Woodstock’s creative corridor to visit Candlestock, a family-owned candlemaker and workshop since 1970, that produces candles using sustainably sourced local beeswax and essential oils. Nearby, Clouds Gallery, now in its 51st year, celebrates independent American craft with a refined mix of glass, jewelry, woodwork, and more. Next, visit the Woodstock Artists Association & Museum, founded in 1919 and dedicated to showcasing works created within a 50-mile radius, along with exhibitions, panels, screenings, and artist talks that highlight the region’s enduring creative community. Just next door, the Byrdcliffe Kleinert/James Center for the Arts provides another hub for local exhibitions, concerts, readings, and multidisciplinary programming. Stay for a live-music-filled evening with dinner and acoustic sets at Pearl Moon, then catch a show at Colony, a 1929-built venue hosting national acts and beloved local cover bands.
Saturday
Over the past few years, Kingston has emerged as the next frontier for the Mid-Hudson creative class: an eclectic mix of makers, artists, and chefs operating with a distinctly hand-touched sensibility.
Begin at Rosie General, an artisan bakery, deli, and provisions shop where almost everything is scratch-made or sourced from nearby farms. Don’t miss the egg toast on house-made sourdough with braised greens, white beans, a soft-poached egg, and chile crisp.
From there, visit two neighboring cultural gems: the Center for Photography at Woodstock (CPW) and International Museum of Dinnerware Design (IMoDD). Housed in a former cigar factory and bottling plant, CPW now features international-scale artists alongside a community gallery, darkroom, digital lab, workshops, and screenings. IMoDD, a curatorial project years in the making and newly permanent as of 2025, celebrates the global artistry of dinnerware with rare pieces and rotating exhibitions. Two blocks away, Kingston Bread & Bar is the perfect lunch stop, known for its house-made breads, local cheeses and meats, and an impressive selection of local kombucha and beer. Spend the afternoon Uptown exploring the Senate House State Historic Site, followed by a glass of wine at Chleo’s. For dinner, head to Restaurant Kinsley, located in a beautifully restored former bank. The menu spotlights hyper-local, seasonal ingredients, and the restaurant often hosts live music—ideal for a pre-show meal before heading to indie venue Assembly.
Sunday
Time it right and cap off the weekend with two singular experiences in nearby Saugerties, each offering a different lens on local bluestone and sculptural work.
Begin with a private tour of Opus 40, the monumental lifelong project of artist Harvey Fite. Over 40 years, Fite transformed more than 60 acres of abandoned quarry into spiraling walkways, terraces, and ramps—each hand-placed slab anchored by a towering central monolith. Initially conceived as an outdoor stone garden, the site evolved into a sculptural environment and now includes a Quarryman’s Museum, plus a calendar of live concerts and community events.
A short drive away, explore Spiral House Park, created by the late artist Tom Gottsleben with his wife, Patty Livingston. Inspired by sacred geometry, the property centers around a visionary home comprising 52 walls that shrink and expand to form perfect spirals ascending to the apex backed by sweeping views of Overlook Mountain, native plantings, woodlands, walking trails and on-site ADA-accessible sculpture park.
Between tours, stop in Woodstock for brunch at Oriole 9 for brunch, featuring fresh-baked pastries from Balthazar, gluten-free selections from Deising’s, and local art for sale.
Where to stay: Channel your inner Joplin or Hendrix at Hotel Dylan, a rock-and-roll-inspired boutique stay where each room includes its own record player and access to the hotel’s vinyl library.
