This free-spirited, flower-powered mountain town and countercultural mecca for generations of creative types never actually hosted its namesake music festival back in ‘69 (that legendary concert phenomenon instead unfolded in Bethel, New York, some 60 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 arts colony (beginning with the still-running Byrdcliffe Arts Colony back in 1902) 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 the peace and love.
01 of 08
Go Shopping On and Around Tinker Street
Tinker Street, Mill Hill Road, and the other streets that offshoot Woodstock’s heart at its 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 workshops/readings (tip: don’t miss a tarot reading from Florentine reader/intuitive Silvia Forni).
Also worth seeking out: The Mower’s Flea Market on weekends from May through November (and on Wednesdays in July and August), as well as local farmers’ market Woodstock Farm Festival, on Wednesdays held from late May to mid-October.
02 of 08
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; it was founded by the late music-industry bigwig Albert Grossman, who managed names like Dylan, Janis Joplin, and The Band. At the storied Midnight Rambles, sporadic jam sessions are held at the barn/studios of the late The Band drummer Levon Helm, which are "helmed" today by his daughter and fellow musician, Amy Helm (happily, for the less nocturnal, the acts usually start closer to 8pm). The longest-running 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’s known for its stellar... acoustics.
Back in town, the recently restored Colony Woodstock pairs live music with historic atmosphere in its 1929 ballroom while the late-night The Lodge features open mic nights on Tuesdays and live bands on Fridays. Feeling inspired? Pick up your own musical instrument memento from town retailer Woodstock Music Shop.
03 of 08
Kick Back at the Village Green
Give in to gravity at the village green, Woodstock’s town center and a prime perch for people-watching. Watch the parade of local aging hippies (including some festival leftovers) and visiting hipsters, artists and musicians, pups and protesters, and perhaps even the occasional celebrity (especially of the local ilk, like town fixture Allyn Richardson, aka Grandpa Woodstock) filter through.
While you may come across a guitar being strum on the green at any given time, you’re guaranteed to catch some tunes on summer Saturday afternoons, courtesy of the free, all-ages Concerts on the Green series. Or follow the beat here on Sunday afternoons (from 4 p.m. to 6 p.m.) when the weekly drum circle is held.
04 of 08
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 would follow suit in the years that followed, many of which still maintaining a presence today, like the Maverick Art Colony, now home to the above-mentioned Maverick Concerts (founded in 1905); the Woodstock School of Art, a center for year-round arts... classes (with history dating to 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).
Other notable galleries and exhibition spaces include the Elena Zang Gallery, showcasing contemporary art from Hudson Valley artists (don’t miss the on-site sculpture garden), and the Fletcher Gallery, specialized in early 20th century American art. (Tip: Pay your respects to Woodstock-tied artists of yore at the Woodstock Artists Cemetery, set within walking distance of the village green.)Continue to 5 of 8 below.
05 of 08
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, 2.4-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 (more on that next), 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!)
06 of 08
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’s 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.
07 of 08
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 from October 10-14, 2018.
08 of 08
See a Play at the Woodstock Playhouse
The Woodstock Playhouse opened in 1938, and 80 years 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), the 2018 lineup includes productions like Damn Yankees, The Music Man, and La Cage aux Folles.