Woodstock, NY is one of those towns where you arrive and you instantly start Zillow-ing houses and daydreaming what it would be like to own a little cabin in the Catskills. There’s much to its appeal: For starters, the small town is known for its music culture being home to Bob Dylan and other musicians. (However, contrary to popular belief, the famous Woodstock festival of 1969 wasn’t actually held in Woodstock due to venue issues — it was in Bethel, NY — but kept the name). If you live in NYC, it’s a short, two-hour drive where there’s plenty of quirky lodging, creative places to eat, and nature to soak in. In addition to the great culture inspired by music and the arts, you’ll fall in love with Woodstock’s spirit where “peace and love” are actually a way of life and not just a groovy phrase you’ll find emblazoned on throw pillows (though there are plenty of those, too). If after one weekend away in Woodstock you’re already booking your return trip, well, we warned you.
Where To Stay
The Herwood Inn ($$$)
This LGBTQ+ and woman-owned getaway captures Woodstock’s boho energy with curated vinyl collections in every room, a communal hot tub plus firepit, rentable bikes during warm weather, and free yoga on the patio. All four rental rooms (which accommodate two to four people in each) are named after female musicians. There’s the King Suite (named after Carole King), the Franklin Flat (Aretha Franklin), Nick’s Nook (Stevie Nicks), and Mitchell Manor (for Joni Mitchell). There’s also The Commune, which is a shared indoor space that features a gift shop — though it’s closed for COVID-19 safety precautions, you can order CBD products, perfumes, and other trinkets from the shop on your room’s iPad.
Hotel Woodstock Way ($$$)
Each of the 10 suites at Woodstock Way features a private outdoor space, comfortable furniture, and funky decor that’s a combination of both rustic and contemporary. The sound of the nearby waterfall and babbling brook can be heard from any of the rooms to make you feel like you’re tucked away in a remote location — yet you’re still within walking distance to restaurants and cafés, which are incredibly convenient.
The Hotel Dylan ($$)
Designers (and husband and wife duo) Robert and Cortney Novogatz transformed a former truck stop motel into this luxe, hippie retreat where no detail was overlooked. Most hotels have minimal, cookie-cutter necessities (a bed, a desk…), but The Hotel Dylan makes it feel a little more like home with record players, throw pillows, stacks of books, and Tempaper wallpaper that give it tons of personality. Enjoy in-house wellness services (by appointment) that range from in-room massages to private yoga instruction to healing sessions from a Reiki master to help you connect to the spiritual world. The 22 guest rooms overlook a central lawn with a new-ish lobby that’s an ideal space for playing board games, reading, or grabbing a continental breakfast on the weekends. There’s also a pool on-site, two fire pits, and a hammock that completes the relaxing, laid-back vibe. If you’re hungry, no need to go far: The on-premise restaurant and bar, Santa Fe Woodstock, features Mexican cuisine and a sophisticated ambiance.
Where To Eat and Drink
Cucina
On the main drag in Woodstock, you’ll instantly be able to spot this rustic yellow farmhouse with its gorgeous wraparound porch. To the left of the modern Italian eatery is the barn where private events are held. Opened by Chef Gianni Scappin (who has cooked at legendary hotels and restaurants throughout Italy) and Lois Freedman (the president and CEO of the legendary Jean-Georges restaurants around the world). You can’t go wrong with any of the pastas or pizzas, naturally, and their smart wine menu denotes wines and wineries that practice organic and/or sustainable farming methods.
Shindig
Ryan Giuliani got the help of old friends — Jennifer Potenza, Allison Garskof, and Lukus Hasensta who also happened to be the owners of go-to NYC brunch spot Penelope — to open Shindig in the heart of Woodstock. The inviting, casual space (a mixture of booths, small tables, and stools at the bar) seats up to 30 people and touts a menu that’s centered around comfort food like tomato soup, the Shindig burger (featuring an addictive, smoky sauce), grilled cheese, and banana pancakes. They even have a coffee takeout window if you just need a pick-me-up in between hiking or shopping. Closed on Mondays and Tuesdays, they’re open for lunch, dinner, and weekend brunch.
Phoenicia Diner
Just 20 minutes west of Woodstock is this first-come, first-serve diner that’s so famous that there’s often a line snaking into the parking lot during busy weekend brunch hours. There’s plenty of outdoor space to enjoy the fresh Catskills air. You’ll find breakfast classics served all day like buttermilk pancakes, omelets with locally sourced mushrooms, or biscuits and gravy. Plus, they have a solid lunch menu of sandwiches, burgers, salads, and more. If you’re a fan of brunch cocktails, make sure to order the Bloody Mary. Want a preview of the menu? You can purchase the Phoenicia Diner Cookbook co-authored by the diner’s chef, Chris Bradley, to try out any of the 85 comfort food recipes. They’re open Thursday – Tuesday from 8 a.m. – 6 p.m. and closed on Wednesdays.
Silvia
Korean sisters, Doris and Betty Choi, renovated this former rock ‘n’ roll dive bar into an elegant restaurant that centers around an open kitchen and wood-fired grill. Doris, who has over 20 years of restaurant experience, puts a Korean flair to the contemporary, seasonal menu where every item is locally sourced and organic whenever possible. Best for a special night out (entrées start at $24), you’ll love both the fancier vibe indoors and the more casual vibe on the patio while sitting under twinkly lights and plenty of greenery. Menu highlights include oysters, Korean BBQ beef, bibimbap, and guilt-free vegan strawberry cake. It’s open every day, starting at 5 p.m.
What To Do
The Golden Notebook
This indie bookstore, named after the original owner’s favorite novel, opened in 1978. It’s the type of place where the staff is on a first-name basis with locals and can talk about book recommendations about any genre all day long. In partnership with Woodstock Book Fest, the bookstore has hosted events featuring Pulitzer Prize winners, in addition to book fairs that support local schools, author meet-and-greets, and more. It’s open daily from 11 a.m. to 5 p.m.
Ashokan Reservoir Promenade
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Just 15 minutes south of Woodstock is the gorgeous Ashokan Reservoir, which is one of the water sources that provides NYC its drinking water. You’ll find many different trails that lead to the reservoir, but the promenade is an easy, almost 3-mile walk that provides the best views of the Catskill mountains. It’s paved and flat so it’s great for walkers and bikers (and it’s ADA compliant). Soak in the amazing scenery — you’ll probably even spot a bald eagle or two.
Midnight Ramble
Midnight Ramble is a concert series held at the private residence (a.k.a. it’s closed to the public outside of show hours) of the late Levon Helm who Rolling Stone once called “rock ‘n’ roll’s greatest drummer.” Helm originally started doing these concerts in his home studio to raise extra money to help with medical bills from throat cancer in the early 2000s. Now operated by volunteers, the legacy of the Midnight Ramble continues with various artists who have included Billy Bob Thornton, Norah Jones, Elvis Costello, Garth Hudson, and others. Make sure to grab your tickets online (they’re not sold at the door), and a reusable metal or plastic cup with the beverage of your choice (rosé, anyone?) as cans/bottles aren’t allowed on the premises.
Karma Triyana Dharmachakra
Directly across the Overlook Mountain trails, pay a visit to the Tibetan Buddhist Monastery to revive your spirit and find a moment of peace. It is the North American monastic seat of the Gyalwa Karmapa Ogyen Trinley Dorje, the head of the Karma Kagyu lineage of Tibetan Buddhism. On weekdays, roam the grounds from 10 a.m. to 5 p.m. and join the Chenrezik sadhana and mantra chant from 7 p.m. to 8 p.m.
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