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Vogue’s Guide to the Most Famous Small Town in the World: Woodstock, New York
OCTOBER 6, 2014 12:00 PM
In Vogue’s October issue, longtime Manhattanite Jonathan Van Meter writes of his recent decision to leave the city and relocate to Woodstock, “where the 1969 music festival famously didn’t take place.” Jonathan already owned a house in Woodstock, which he’d bought five years earlier, after having visited the town only once. The place seems to have this effect on people. I too rashly bought a house in Woodstock after visiting only once. My husband and I first went four years ago to see a friend who was recording an album there. On a perfect fall night, a group of us went to the Midnight Ramble, the concert series held at the late drummer Levon Helm’s home studio, where for a few hours we watched Levon play with Steve Earle and shuttled between a potluck spread inside and a bonfire outside under the stars. That was it. On our second trip to Woodstock, we laid down our life savings on a cabin in the woods that we found on Craigslist. It’s an often repeated joke that Woodstock is made up of people who don’t realize the concert is over, but the truth is it’s filled with all kinds of people—an “oddball menagerie,” as Jonathan puts it—and was a haven for artists long before the festival that wore its name. Did we mention it’s only two hours from New York City? Below, we’ve compiled a list of the places you’ll want to visit over a weekend there. If afterward you find yourself combing real-estate listings, don’t say we didn’t warn you.

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Phoenicia Diner
This gem on Route 28 is where you want to fuel up before or after a hike. Be forewarned that if you order one of their skillet dishes, you may not be hungry for dinner, or ever again. Another terrific breakfast and lunch spot is Oriole 9, which serves strong coffee and excellent huevos rancheros.
Photo: Courtesy of Upstate Stock / @upstatestock
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There are stunning hikes all around the area. The shortest with the biggest payoff is the one-mile trail to Kaaterskill Falls, pictured here, a two-drop waterfall and frequent subject of the Hudson River School painters. The two and a half-mile hike to Huckleberry Point is shaded and rambling and worth it for the sweeping view of Plattekill Clove. The trail from the Tibetan Buddhist monastery to Overlook Mountain is also two-and-a-half-miles, and uphill the whole way, but leads to a fantastic view of the Hudson and surrounding Catskills.
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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The Graham & Co.
This relatively new 20-room motel in the nearby town of Phoenicia is owned by four Brooklyn-based friends who work in design, and it shows. There’s a swimming pool, hammocks, a badminton court, a fire pit, and cruiser bikes. Closer to Woodstock is the new Hotel Dylan, whose tagline, naturally, is “Peace. Love. Stay.”
Photo: Courtesy of The Graham & Co. / @thegrahamandco

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Woodstock Way
This cluster of charming historic cabins, along a stream right in the middle of town, was recently bought by Ryan Giuliani, and his wife, Mary Giuliani, caterer to the stars. They have done a lovely, painstaking renovation, and the location couldn’t be better.
Photo: Courtesy of Cindy Halliburton
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The Center for Photography at Woodstock
This non-profit exhibition space was founded in 1977 by Howard Greenberg, owner of the gallery on East Fifty-Seventh, and it offers a terrific roster of shows, speakers, and programs. (Past instructors: Richard Misrach, Sally Mann, and Arnold Newman.) Bonus: It’s housed in the building that was once Café Espresso, the bar where Bob Dylan and Joan Baez played in the sixties. The Elena Zang Gallery also shows great work, and when they host openings, the whole town shows up.
Photo: Courtesy of Lef Carroll / @lef_iv
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Garden Café on the Green
If you don’t like the vegan food here, you don’t like vegan food. With dishes like Indian chickpea enchiladas and exceptional build-your-own macro bowls, it’s a hub for Woodstock’s health-nut contingent, including green-juice motivational speaker Kris Carr. Sunfrost Farms, an organic grocery with an attached café and juice bar, is another great spot.
Photo: Courtesy of Lauren Lynch / @laurenlynchh

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Opus 40
A retired art professor from Bard and quarryman named Harvey Fite spent 37 years building this six-acre maze of a sculpture out of bluestone. Fite worked alone, using only hand tools. The site is now a sculpture park and museum, and an awesome place to spend a Sunday.
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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There are a number of great antique shops on Tinker Street, and in the nearby town of Saugerties, clustered around the intersection of Main and Partition Streets. Standouts are Scandinavian Grace, pictured here, which has a small but cool selection alongside new Scandi homeware; Resource Gallery, owned by the dealer James Morrison; and Time and Materials, owned by Tom Luciano.
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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The Golden Notebook
The little independent bookstore that could, the Golden Notebook stocks a selection to satisfy die-hard readers, holds more than a hundred author events a year, and partners closely with the Woodstock Writers Festival, run by Martha Frankel (former New York City editor, writer, and bon vivant), to bring internationally known writers to town.
Photo: Courtesy of Azita A. / azitaloves

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Woodstock Farm Animal Sanctuary
Where rescued farm animals live the good life. Goats, turkeys, and more roam free and are cared for by two former film people who used to work with Errol Morris. (Word to the wise: unless you want the biography of every chicken in the chicken coop, skip the guided tour.)
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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Byrdcliffe Theater
The Byrdcliffe Arts Colony, one of the country’s first utopian arts communities (past visitors: Isadora Duncan, Bob Dylan), has two great venues: the theater on its 300-acre campus, shown here, and a gallery space on Tinker Street. There’s always something good going on at The Woodstock Playhouse, and at the Bearsville Theater, the latter of which is the brainchild of Albert Grossman, the music-industry honcho who managed Janis Joplin, Odetta, Bob Dylan, and The Band, among others.
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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Swimming Holes
More of a summer activity, but the area’s watering holes are one of its biggest draws. The Millstream, pictured here, is right downtown and one of the most popular. Big Deep is not far and a bit larger. Fawn’s Leap is further afield but very gorgeous.
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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Woodstock Film Festival
Woodstock’s annual film festival bills itself as “fiercely independent” and lives up to the promise with a program heavy on international features and documentaries, a good portion of which screen at the Woodstock location of Upstate Films, pictured here. This year’s festival is right around the corner: it starts on October 15 and runs through October 19.
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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It ain’t the Rockies but the skiing upstate is still totally fun and easily the best way to cope with a polar vortex. The closest and the tallest is Hunter Mountain, pictured here, which also has a crazy-high zip line that you can ride in the summer months. Windham Mountain is generally less crowded and a little more ideal for beginners. For cross-country, you can’t do better than the trails on the expansive property of the ridiculously picturesque Mohonk Mountain House in New Paltz.
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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Hippie Merch
Close readers of Vogue.com know that tie-dye is back, from the runway to home décor. You can pick up shirts, scarves, and onesies at the stand pictured here, which is set up near the village green during the warm months. There is also the year-round Not Fade Away should you need, say, tie-dyed shoelaces or a Pink Floyd change purse.
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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Woodstock General Store
The Steven Alan of Woodstock, if that’s possible. This store on Tinker Street stocks Fjällräven parkas, Baggu bags, No.6 clogs, great wool socks and gloves, and the most amazing 100 percent argan oil, which the owner, Nabile Taslimant, gets directly from his family’s village in Morocco.
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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There are beautiful roads and some pretty serious climbs all around these parts. If you don’t have a bike you can rent one in town from the excellent Overlook Mountain Bikes, where you can also pick up cycling maps with suggested routes of varying length. Two particularly scenic rides are around Cooper Lake, shown here, or along the Ashokan Reservoir Dam.
Photo: Courtesy of Abby Aguirre / @abbyaguirre
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This Italian spot serves delicious pizza and pasta on the wraparound porch of an old farmhouse and is co-owned by Lois Freedman, president of the Jean-Georges empire. Two other Woodstock institutions are The Bear Cafe, which serves hearty mountain fare streamside, and Yum Yum Noodle Bar, whose bibimbap and Korean tacos are addictive.
Photo: Courtesy of Dana McCullough (via Foursquare)
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Somewhat counterintuitively, Woodstock is a great tennis destination. There’s the Woodstock Tennis Club, as well as Total Tennis in Saugerties, pictured here, a world-class camp with 20 outdoor courts and a superstar teacher named Ty Dennis.
Photo: Courtesy of Sean Cutick / @sean.cutick
Woodstock New York


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