In the early 1960s, when newly famous Bob Dylan needed to escape New York City — where constant fan attention was becoming a drag — he moved upstate and into the guest quarters of his manager’s vacation home in Woodstock, an artsy village on the edge of the Catskill mountains. There he rode (and famously crashed) his motorcycle along winding roads and lounged around Café Espresso on Tinker Street, the town’s main thoroughfare. “Soon Dylan was spending so much time at the Espresso — drinking coffee, playing chess, reading The New York Times — that the [owners] asked if he wanted to work in the room above it,” music journalist Barney Hoskyns writes in his book Small Town Talk, which explores the village’s musical pedigree. The typewriter-equipped upstairs bedroom became Dylan’s hideaway — and a favorite writing spot.
I’m standing on the balcony outside my room at the recently opened Woodstock Way Hotel (845-684-5911, woodstockway.com), gazing the 100 yards toward the rear windows of Dylan’s old haunt, which is now the Center for Photography, an arts nonprofit. The boutique hotel, which opened last fall, celebrates this region’s musical legacy. Photos in the lobby recall the 1969 Woodstock concert festival (which, due to zoning disputes, actually took place 60 miles from here). All rooms feature coffee-table books commemorating the concert, plush bathrobes, CBD-infused drinks in the minibar, and an outdoor firepit overlooking a small waterfall. Our room is also equipped with Bluetooth turntables and Bose speakers and a small collection of vinyl that includes The Monkees, Wings, Steve Martin, and Blues Traveler. The hotel is a two-minute walk from the heart of the village and proves an ideal spot for my wife and me to spend our anniversary weekend.
It’s our first time here, but I’ve been hearing about Woodstock for years. In the 1990s, when I worked at a magazine in New York, several high-ranking editors had summer places here, in keeping with the cultural stereotype: Wall Streeters head east to the Hamptons, creatives head north to the Catskills. Although The New York Times recently reported that this region is seeing a rise in multimillion-dollar properties, we see little evidence of this glitzification. Instead, we observe ramshackle rural homes, art galleries, and a noticeable lack of trendy chains (not a Starbucks or a SoulCycle in sight). Despite too many souvenir stores hawking ’60s-era memorabilia, Woodstock remains noticeably chill even as the 50th anniversary of the famed concert approaches this August.
We begin our first morning by heading 3 miles out of town to the Karma Triyana Dharmachakra (845-679-5906, kagyu.org), one of the largest Tibetan Buddhist monasteries in the United States. Each day it opens its doors to the public at 6 a.m., and by 8:30 a.m., we find ourselves perched on round, firm pillows inside the main temple as a volunteer taps a resting bell and begins chanting. She repeats the lines three times in Tibetan, then once in English. (“From the stormy waves of birth, old age, sickness, and death / from the ocean of samsara, may I free all beings.”) For the next 25 minutes, my wife and I, along with two others, sit in silence, meditating. After a five-minute break to stretch and chat, a new volunteer solemnly announces, “sitting meditation” and rings the bell, and we sit in silence some more. Driving back toward town afterward, hips sore from an hour on the pillows, we notice how many houses are adorned with fluttering multicolored prayer flags, a sign that the counterculture spirit of the ’60s is alive and well.
But humans require more than spiritual sustenance, and on that front there’s good news: Woodstock knows how to cook. For breakfast, start at The Mud Club (themudclub.com), which opens at 7 a.m. and offers bagels cooked in a wood-fired oven, or try the all-vegetarian (and mostly vegan) fare at the Garden Cafe (845-679-3600; thegardencafewoodstock.com), which also offers brunch-appropriate cocktails. For lunch, stop by Tinker Taco Lab (845-679-8226, facebook.com/tinkertacolab), which goes beyond the basics to offer more unusual items such as beef tongue tacos, fried avocado tacos, and yam tamales. For snacks, go to Nancy’s (845-684-5329, nancysartisanal.com) for artisanal ice cream, or Peace, Love and Cupcakes (845-247-3687, woodstockcupcakes.com), whose treats are named after musicians who played the 1969 festival.
At dinner, fancier options abound. Cucina (845-679-9800, cucinawoodstock.com) offers contemporary Italian fare in a rambling yellow farmhouse just east of downtown. Forgoing the long communal table, we take a two-top near a front window, from which we imagine dining al fresco on the wide porch on a warmer, drier summer night. The food — bruschetta with prosciutto, fig spread, and burrata, followed by orecchiette with lobster, roasted tomato, and jalapeño — is imaginative and hearty. If we lived nearby, we’d eat here often.
For Saturday night dining, locals suggest upscale Silvia in the heart of downtown (but it’s fully booked), Miss Lucy’s Kitchen in Saugerties (a 10-mile drive), or The Red Onion (3 miles from downtown). We prefer to stay within walking distance of our hotel, so we type “vegetarian” into the Yelp search field and take a chance on Woodstock Pizza Theater (845-679-2700, woodstockpizzatheater.com), on the western edge of downtown. Although less renowned than Cucina and Silvia, the Pizza Theater proves a fine option for a more casual, less expensive meal. The menu is peppered with vegan and “vegetarian option available” items, including many with house-made meat alternatives that use tempeh or seitan. Its pizza, with a slightly salty, spongy-light crust, proves impossible to stop eating; a tuna, shrimp, and chicken taco special arrives with a homemade coconut-cilantro sauce I’d spoon over anything. As we linger at the bar watching a ballgame, the chef joins us to chat.
There’s no shortage of live music options on many evenings in Woodstock. During our weekend stay, we’re uninterested in the folk singer playing at The Colony, a renovated concert hall that offers ticketed shows, and Levon Helm Studios, the venue created by the drummer from The Band who was a long-time Woodstock resident before his 2012 death, is closed this spring weekend. We grab a drink amid a mostly local crowd at Station Bar & Curio (845-810-0203, stationbarandcurio.com) as a band sets up its gear on the outdoor stage. We consider staying for the show but grow impatient and leave after the bartender’s playlist cycles through Jimi Hendrix’s “Foxey Lady” twice in 20 minutes. (If you go out at night in Woodstock, be prepared to hear a lot of music from the 1960s.)
More contemporary songs emanate from the speakers at A&P Bar (845-684-5395, aandpbar.com), a two-year-old establishment tucked in the rear of what was once Woodstock’s primary supermarket. These days the tall shelves of bottles highlight A&P’s status as the region’s cocktail mecca. At 9 p.m. on a Saturday in July, this area would be jammed with patrons — but tonight there’s just a handful of people finishing meals or enjoying a nightcap. Bartender Carl Bester prepares one of his signature drinks, the Dawa: apple vodka, lime, mandarin orange, and sugar, which is served with a thick wooden muddler coated in whipped honey. “It’s a different drink with every sip,” Bester says, explaining how the gooey honey slowly melts into the drink. He’s right: It starts out astringent and vodka-dominant, but by the last sip, the honey’s sweetness has mellowed and balanced everything out.
As we drink and talk, Bester pours, stirs, sniffs, and tastes. He’s experimenting. He takes a sip from a new drink and passes me the glass. It’s the same cocktail I’m drinking, but he’s replaced the apple vodka with a curried vodka. To me it tastes like a boozy Thanksgiving side dish, but Bester raves about its complexity, passing the glass to waitstaff and fellow patrons. Next he takes a Mason jar from a high shelf and mixes a new version, this one containing a homemade chili concoction. He sips and grimaces. “Wow. Serious heat.” I sip, immediately regretting it. “TOO HOT,” cries the waitress after her try. Becker tastes again. “I’m going to feel this tomorrow,” he says.
When the weather cooperates, Woodstock is best experienced outdoors: the nearby Catskills offer spectacular hiking. The area’s best-known route goes 2.4 miles up Overlook Mountain. Partway up lie the remains of an abandoned 1920s hotel; at the top of the 3,150-foot peak is a fire tower offering Instagram-worthy views. It rained at the start of our weekend, but late one afternoon, as things begin drying out, we drive up the curvy mountain road to the trail.
This turns out to be a popular idea: The parking lot is jammed, so we follow signs to a satellite lot that adds an extra mile of walking (each way) just to get to the trailhead. We start off enthusiastically. Our energy ebbs slightly as the trail (and our pants and shoes) become muddy. Although the trail’s website describes it as a “gradual but nonstop incline” that rises 1,370 feet, it feels far steeper than that. The mud makes it slippery and slow going. Winded, I stop for a break.
It’s now 4 p.m., we’re only halfway up, and most of the other hikers we encounter are on their way down. In theory we have at least two hours until sundown, but this is starting to feel like one of those Everest disaster movies in which the protagonists’ irrational pursuit of the peak leaves them in the “death zone” as temperatures drop and daylight wanes. I suggest we turn around.
My wife ponders our options. “If we bail, are you going to say it was because of safety, or because you’re out of shape?” she asks.
“Definitely safety,” I say between breaths.
Tired and back in our hotel room, we put a record on the turntable and pull out our phones, Googling to see who can find the best photo from the top of the mountain we failed to climb. The views remind us of the lyric from The Who: “I can see for miles and miles” — and provide yet another reminder of why Dylan and so many others found this area so special. Next time, with better weather and an earlier start, we plan to see that vista for ourselves.
Daniel McGinn is a senior editor at Harvard Business Review. Send comments to firstname.lastname@example.org. Get the best of the magazine’s award-winning stories and features right in your e-mail inbox every Sunday. Sign up here.
BY THE TIME WE GOT TO BETHEL
Travel writers are supposed to know the ins and outs — to show you the way. Sometimes, however, they provide a cautionary tale. This is one of those times.
Imagine you’re visiting Woodstock. You like music and history, so of course you want to visit the site of the 1969 music festival. You know the concert actually took place miles away in Bethel, now site of the Bethel Woods Center for the Arts (845-583-2079, bethelwoodscenter.org), which contains a Woodstock museum. But it’s a nice day for a drive. Why not tuck a trip to Bethel into your weekend in Woodstock?
Bad move. The 60-mile drive, on rural roads with village speed limits routinely dipping down to 30 miles per hour, takes longer than you’d expect. (Figure at least 90 minutes.) And because Bethel is southwest of Woodstock, if you’re heading back to Boston after your museum diversion, you’ve just added 50 miles to the drive home. (Figure on four hours back to Boston.)
The museum is hosting a special exhibition celebrating the 50th anniversary of the concert, featuring memorabilia, photography, and films. Many of the docents leading tours attended the concert themselves. Together, the exhibits do a fine job of explaining how 400,000 people flocked to nearby fields for “3 Days of Peace and Music” — and places the event in context against the backdrop of the Vietnam War and the social unrest of the 1960s. The surrounding fields, once Max Yasgur’s dairy farm, are open to the public during the summer.
So if you’re especially interested in ’60s history and culture, by all means plan a visit, and consider seeing a show while you’re there: Dave Matthews, Jackson Browne, Elvis Costello, and Sheryl Crow are all playing the grounds at Bethel Woods this summer.
But unless you enjoy long road trips, don’t try to experience Woodstock-the-concert and Woodstock-the-village in the same weekend. Make separate trips.