This free-spirited, flower-powered mountain town and the countercultural mecca for generations of creative types never actually hosted its namesake music festival back in 1969 (that legendary concert phenomenon instead unfolded in Bethel, New York, some 80 miles away). But it was indeed the tenacious bohemian spirit of liberal and artsy Woodstock—nestled in New York’s Catskill Mountains, about two hours north of New York City—that birthed not only the festival concept but the breeding ground for myriad arts and music movements for more than a century.
Look beyond the kitschy, tie-dye-laden head shops and weekend tourist jams, and you’ll find this hippie haven has real heart. Pulling from its longstanding tradition as an art colony and strong spirit of tolerance, laid-back Woodstock brims with diversions aplenty: eclectic shops, live music venues, art institutions, and mighty mountain environs that foster Zen-seeking and adventures in the great outdoors. All you need to bring is peace and love.
Ride the Longest Zipline in North America
It's not just the longest zipline in North America, but also the highest and the fastest. Located on Hunter Mountain just 20 miles outside of Woodstock, one of the adventure packages from Zipline New York is the most exhilarating way to take in the breathtaking Upstate landscape. Adventure tours last from two to three hours, but the SkyRider tour is the most intense for the ultimate thrillseekers with ziplines 600 feet above the ground and 3,200 feet long.
If you want less of a rush, then mid-mountain packages are available for exciting rides that don't venture quite as high. To finish off the experience with a bang, participants will have to rappel down a 65-foot wall.
Pick Organic Produce at a Local Farm
The quintessential small-town farm, Sunfrost Farms is the perfect place to spend a day picking up locally grown fruits, vegetables, mushrooms, and flowers. There's nowhere better to grab the freshest in-season products, from juicy summer tomatoes to seasonal fall pumpkins. While the market and farm are worth a visit alone, the true highlight of Sunfrost is the organic cafe. Baristas prepare fresh-pressed juices made from locally grown produce to accompany the menu of high-quality bites. Try a breakfast sandwich made with freshly-laid eggs in the morning or one of the homemade soups of the day, among many other options.
Go Shopping on Tinker Street
Tinker Street, Mill Hill Road, and the other streets that offshoot Woodstock’s heart at Village Green make for a wonderfully walkable stretch lined with colorful and quirky mom-and-pop boutiques hawking everything from the requisite tie-dyes and New Age-y crystals to Tibetan crafts and women’s fashions.
Some favorites include mainstay The Golden Notebook, an indie bookstore and community hub; Candlestock for all types of handmade candles; Tibetan Arts and Crafts for authentic Tibetan handicrafts; Fruition Chocolate for award-winning, small-batch chocolates; and Mirabai of Woodstock for spiritually-minded trinkets, books, and special workshops.
Also worth seeking out is the Mower’s Flea Market on weekends from May through November (and also on Wednesdays in July and August), as well as the local farmers’ market Woodstock Farm Festival, held on Wednesdays from late May to mid-October.
Listen to Live Music
Longtime resident Bob Dylan is said to have quipped that you only had to throw a stone and you’d hit a musician in Woodstock. For the less antagonistic among you, an even better bet is to head out to one of the town’s music venues, where you can catch local and national talent almost any night of the week.
Try the streamside Bearsville Theater for weekly indie and alternative acts, founded by the late music-industry bigwig Albert Grossman, who managed names like Bob Dylan, Janis Joplin, and The Band. At the storied Levon Helm Studios, sporadic jam sessions are held at the barn of the late The Band drummer, Levon Helm, which is "helmed" today by his daughter and fellow musician, Amy Helm (happily, for the less nocturnal, the acts usually start closer to 8 p.m.). The oldest, continuous chamber music festival in the U.S., the summertime Maverick Concerts series, was founded in 1916 and runs in a historic, rustic concert hall in the Woodstock woods that are known for its stellar acoustics.
Back in town, the recently restored Colony Woodstock pairs live music with a historic atmosphere in its 1929 ballroom. Feeling inspired? Pick up your own musical instrument memento from town retailer Woodstock Music Shop.
Get Your Art Fix
While Woodstock may ring synonymous with music, the town’s creative roots largely derive from an arts and crafts movement. In 1902, a utopian arts colony envisioned by well-to-do Englishman Ralph Whitehead was founded here in the form of the still-standing Byrdcliffe, one of the country’s oldest arts colonies and a development that would prove pivotal in changing the cultural landscape of Woodstock. Still today, the 250-acre arts-and-crafts colony, managed by the Woodstock Byrdcliffe Guild, maintains a multicultural residency program for artists of all stripes while putting on public events like classes, exhibitions, and performances at its Kleinert/James Arts Center. Guided summer tours are also available.
Additional creative operations followed suit, such as the Woodstock School of Art, a center for year-round arts classes (started in 1906); the Woodstock Artists Association and Museum, which puts on multi-medium exhibits by area artists (established in 1919); and the Center for Photography at Woodstock for photo exhibits and workshops (dating to 1977).
Anther notable exhibition space is the Elena Zang Gallery, showcasing contemporary art from Hudson Valley artists (don’t miss the on-site sculpture garden). Round out your artistic experience by paying your respects to Woodstock-tied artists of yore at the Woodstock Artists Cemetery, set within walking distance of the Village Green.
Head out for a Hike on Overlook Mountain
It’s Woodstock’s bucolic mountain setting that has made it the muse that it is for the artists and musicians who have poured through here over the years. Appreciate the best of that natural beauty atop Overlook Mountain, where a steep, 4.6-mile uphill trek to a summit of 3,140 feet rewards hikers with jaw-dropping Hudson Valley and Catskill Mountain views from a cliff-top perch.
Pick up the wooded trailhead along an old carriage road across the street from the Karma Triyana Dharmachakra (KTD) Tibetan Buddhist monastery, which leads to some notable diversions along the way to the stellar overlook, like the ruins of the old Overlook Mountain House hotel and a fire tower you can climb for some bonus altitude (Warning: keep an eye out for rattlesnakes en route!).
Get Zen at the KTD Monastery
Back down the trailhead, don’t miss a peek at the Karma Triyana Dharmachakra (KTD) Monastery, which looks like it could have been plucked from a Himalayan mountainside and transferred here. The Tibetan Buddhist monastery has a bookstore and there’s a colorful temple filled with ornate shrines that is open to all (when teachings aren’t in session). Free guided tours are available on weekends and Tibetan Buddhism teachings (including meditation courses) are offered to the public via classes and retreats throughout the year.
Catch a Flick at the Woodstock Film Festival
Film buffs should time their visit to coincide with the annual fall Woodstock Film Festival, billed as “fiercely independent” and featuring programming that’s chockablock with indie features and documentaries showcasing emerging and established talent. Apart from the screenings, expect plenty of panels, parties, and the company of industry, media, and celebrity attendees (like Uma Thurman, Natalie Portman, Paul Rudd, to name a few past participants).
Woodstock screenings unfold largely at the town’s movie house Upstate Films, set within an old, steepled Methodist church—a good spot to see an indie film any time of year (more festival films are shown in neighboring towns like Rhinebeck, Kingston, Rosendale, and Saugerties). The event unfolds around early October each year.
See a Play at the Woodstock Playhouse
The Woodstock Playhouse opened in 1938 and almost a century later, it's still entertaining locals and visitors alike via its lively summer stock musical theater programming and historic atmosphere. Rebuilt in 2000 in a design reminiscent of the original playhouse (which succumbed to a fire years before), past lineups have included productions like Damn Yankees, The Music Man, and La Cage aux Folles.