Woodstock: A new generation meets the OG Catskills getaway

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The cozy backyard at the Herwood Inn, complete with a fireplace and a cedar hot tub. Photo: Kara Zuaro.

Fifty years after the music fest that made it famous, Woodstock is still dripping with tie-dye, its sidewalks are decked out with hand-painted guitar sculptures, and when you’re on Tinker Street, you can often detect a trace of patchouli in the Catskills breeze. Nowdays, Woodstock’s long-held traditions of local vegan fare, crystals, and head shops appeal to a whole new generation of visitors. Plus, the brand-new Herwood Inn (a mini-paradise in itself) makes Woodstock more walkable than it ever was before. We daresay that this little hippie town is hitting a second renaissance, making it the perfect place to escape the city. Here, you can nourish your mind, body, and soul with cozy accommodations, great food, music, yoga, art, and nature. And you don’t necessarily need a car to do it right.

Macrame swing + highly Instagrammable potted plants = porch life at the must-visit Herwood Inn. Photo: Kara Zuaro.

How to get there

It’s a two-and-a-half-hour drive from Brooklyn to Woodstock, and having a set of wheels will give you access to all the hikes, scenic drives, and nearby towns that you’ll want to visit on an extended trip. However, if you’re just heading up for a weekend and staying on or near the main drag of Tinker Street, a bus ticket is all you need. We’ve had good experiences with the Trailways bus, which delivers passengers from Port Authority to a Woodstock hardware store smack in the middle of town. The LINE bus drops riders right at partner hotels, like the Woodstock Way and the Graham & Co. (located in nearby Phoenecia), but you don’t need to stay at those hotels to ride the bus.

At Woodstock’s Herwood Inn, the rooms are named for Aretha Franklin, Carole King, Joni Mitchell and Stevie Nicks. Photo: Kara Zuaro.

Where to stay

If you’re not renting a car, we’d recommend treating yourself to a splurgey suite at the just-opened Herwood Inn, before everyone finds out about the place and it’s booked for all eternity.

The meticulously designed 4-room hotel is owned and operated by a pair of spunky and savvy young women, Em Atkins & June Peterson, who started their partnership restoring furniture found on the streets of Manhattan. They’d take the salvaged pieces home to a makeshift woodshop in their 1-bedroom Hell’s Kitchen apartment, hence the origin of “her-wood”). At this sustainability-minded inn, each space-efficient room is equipped with a kitchenette, a surprising amount of potted plants, a bedside iPad loaded with into about the room, an illustrated map of Woodstock, and a zodiac crystal chosen by Grateful Gemhead to rep the astrological sign of the luminary musician for whom the suite is named. (Seriously, you cannot get more Woodstock than this.) An amethyst geode adorned a tabletop beside a selection of Carole King records in our King Suite, and the other rooms pay tribute to Aretha Franklin, Joni Mitchell, and Stevie Nicks. Plus, there’s a communal hang-out area with an outdoor fireplace and cedar hot tub, and borrow-able bikes with adorable wood-grained helmets. You don’t have to be a woman to stay at the Herwood, but if you happen to be a lady with a Wing membership, you really won’t want to stay anywhere else.

Another downtown hotel is the well-designed, 12-room Woodstock Way (which happens to be owned by the Giuliani and Halliburton families, so it’s perhaps less crystal-powered), and Hotel Dylan, a 22-room motel with a lot of boho charm, is just a 5-minute drive from Tinker Street’s main drag. Venture a little farther from town to find Kate’s Lazy Meadow a colorful and campy collection of retro 1950’s cabins owned by B-52 Kate Pierson. If you prefer to rent a house, we’ve spent some quality relaxation time in this 3-bedroom mountain villa and this family-friendly modern log house.

At Woodstock brunch spot Oriole 9, the early bird gets the coconut curried tofu hash. Photo: Kara Zuaro.

Where to eat

Eating out

For breakfast and brunch, everybody loves Oriole 9. They open at 8:30 on weekends, and on a recent autumn Saturday, every table was full by 10 a.m. It’s worth the wait for this family-friendly spot, especially if you’re craving a big ol’ plate of chilaquiles or a satisfying hippie breakfast of coconut curried tofu hash.

Your lunch spot is Tinker Taco Lab, which is only open in the afternoons on Fridays, Saturdays, and Sundays, serving killer tacos. Go for their chipotle-barbacoa, pineapple-mahi-mahi, or fried avocado and shishito tacos with some tasty yam or pork tamales on the side.

If you’re in the mood for a sweet afternoon snack, wander into the alleys behind Tinker Street and follow the signs to Peace Love Cupcakes, where the cupcakes are named after classic rockers. We liked the salted caramel Joe Cocker cupcake, but the Pretzel Hippie Chipper Cookie Sandwich, two chocolate chip-pretzel cookies sandwiching a generous layer of pretzel-peanut butter cream, stole the show here. You could also get a few scoops of ice cream at Nancy’s, where classic chocolate, vanilla, and strawberry meet specialty flavors, like sour cream cherry.

For dinner, head to A&P Bar for oysters, buttermilk fried chicken, and steak frites, and their best-in-town cocktails. Their drink menu features classics like negronis and sazeracs alongside original concoctions, like the Kellerman, a bitter, bubbly mix of gin,aperol, house-made ginger beer, and prosecco. If you’ve still got some stamina, head for another round at local favorite, Station Bar.

If you’ve got a few more nights in town, upscale favorites include Cucina for Italian fare, Silvia for vegetable-centric farm-to-table fare, and the locally beloved Red Onion, located in a farmhouse halfway between Woodstock and Saugerties.

Mussels, chorizo, Calabrian chiles and a tangle of bucatini on the table at Woodstock’s Cucina. Photo: Kara Zuaro.

Eating in

If you’ve rented a house (or want to try out the Herwood’s cute little kitchenettes), you’re going to need to do a bit of grocery shopping. Woodstock has some serious veggie-friendly vibes, but for the omnivores among us, Woodstock Meats is the go-to butcher for Hudson Valley pasture-raised meats. Pair some sausages, ribs, chicken, and steak with a selection of well-curated bottles and cans from the cooler at R&R Taproom, and shop for locally grown produce at Sunfrost Market or Sunflower. For an easy breakfast after a late-night feast, hit up the Mud Club for a good cup of coffee and bring home a bunch of bagels, fresh out of the wood-fired oven.

Frank Bango takes the stage at Woodstock’s destination-worthy music venue, Colony. Photo: Kara Zuaro.

What to do

See a show at Colony

It’s true that the 1969 Woodstock festival actually took place 43 miles away in Bethel, NY, but Woodstock remains the quintessential classic rock town, and you really aren’t getting the full experience until you take in some live music. The best place to do this is at Colony, a 90-year-old venue complete with a gorgeous old bar, a billiards room, and a canopy of twinkling string lights over a red-robed stage. Upcoming performers include Thurston Moore, Max Weinberg, Delicate Steve, and the Felice Brothers. And if comedy is more your thing, Colony has also recently hosted Chris Getherd, Gilbert Godfrey, and Eddie Pepitone. It’s an intimate space, so there’s not a bad seat in the house, but if someone you love is performing here, try to score a ticket for one of the upper level seats (which promise the unbeatable sight-lines pictured above) and build a trip around the show.

Take a yoga class

Here’s a good excuse to plan a whole week (or at least a 3-day weekend) in Woodstock: Alison Sinatra of Woodstock Yoga Center only offers her transportive Morning Vinyasa I-II on Wednesdays and Fridays. There are surely very good instructors on the weekends, too, but Sinatra’s been at this studio for over a decade, through three different owners, and not only is the class unique (her breathwork and sequences are atypical of your usual flow class), she’s the funniest yoga teacher you’ll ever practice with. For real. 

In-room coffee service at Woodstock’s welcoming Herwood Inn. Photo: Kara Zuaro.

Go on a hike

There are hiking options for every skill level around Woodstock. If you don’t mind a steep climb (you’ll need cleats for your shoes if there’s snow and ice on the ground), you can hike Overlook Mountain to find some hotel ruins and a fire tower, or you can take a scenic drive along the Shokan Reservoir and can bring a backpack picnic to Vernooy Falls, a moderate hike that leads to a series of beautiful cascading pools. If you want to soak up some nature without a breaking a sweat, the Comeau Property promises a dog-friendly walk through a field and a forest with a stream running through it. And if it’s swimming season, Big Deep Swim Hole is pretty mellow during the week, but busy and loud on the weekends—and parking gets tighter the later you arrive. Another option for swimmers and paddler boarders is Onteora Lake, an easy hike just outside of Woodstock.

See art and shop

If the weather isn’t great, you can roam the galleries at the Woodstock Art Museum or check out the Woodstock Art Exchange, which presents the work of local artists and sometimes offers glass-blowing demonstrations on the weekends. Or maybe you’ll just want to hit the artistic little home goods store, Shop Little House, where you may find the perfect modern rustic souvenir as you admire the well-curated space.

Opus 40, a sculpture park and labyrinth of hand-laid slate. Photo: Brooklyn Doublewide.

Side trips

If you’ve got a car, you’ll want to make time to visit Opus 40, an awe-inspiring sculpture park that’s less than a 15-minute drive from the heart of Woodstock. It’s on the way to Saugerties, a quaint Hudson Valley town with a great little restaurant called Miss Lucy’s Kitchen. If it’s warm enough to eat ice cream outside, find your way to the window of the itsy bitsy ice cream shop Alleyway Ice Cream, which doesn’t have indoor space and closes in the wintertime. Savor a small-batch scoop of Ube Heath Bar Crunch, Black Sesame Caramel, or Buttermilk Strawberry. Flavors vary through the season, but every one we’ve tried has been delicious.

Got more time? Take a 20-minute drive to Kingston, and check out our city guide for info on where to stay, eat, and shop in the creative capital of the Hudson Valley.

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