The Sunday Edit's Travel Guide to Woodstock, NY

Woodstock, NY is among those towns where you arrive and you instantly start Zillow-ing houses and daydreaming what it really would be like to own just a little cabin in the Catskills. There's much to its appeal: To begin with, the little town is renowned for its music culture being home to Bob Dylan along with other musicians. (However, contrary to popular belief, the famous Woodstock festival of 1969 wasn't actually held in Woodstock due to venue issues – it had been in Bethel, NY – but kept the name). If you live in NYC, it is a short, two-hour drive where there's lots of quirky lodging, creative eateries, and nature to soak in. In addition to the great culture inspired by music and also the arts, you'll adore Woodstock's spirit where “peace and love” are actually a means of life and not just a groovy phrase you'll find emblazoned on throw pillows (even though there are lots 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 in the backyard. All rental rooms (which accommodate 2 to 4 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). Additionally, there are The Commune, that is a shared indoor space that includes a gift shop – though it's closed for COVID-19 safety measures, you can find CBD products, perfumes, along with other trinkets in the shop in your room's iPad.

Hotel Woodstock Way ($$$)

Each from the 10 suites at Woodstock Way includes a private outdoor space, comfortable furniture, and funky decor this is a mixture of both rustic and contemporary. The sound of the nearby waterfall and babbling brook can be heard from the rooms to make you feel like you're tucked away in a remote location – yet you're still within easy reach to restaurants and cafés, which are incredibly convenient.

The Hotel Dylan ($$)

Designers (and couple duo) Robert and Cortney Novogatz transformed an old 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 bit more like home with record players, throw pillows, stacks of books, and Tempaper wallpaper that give it a lot of personality. Enjoy in-house wellness services (by appointment) that range from in-room massages to private yoga instruction to healing sessions from the Reiki master to help you connect to the spiritual world. The 22 guest rooms overlook a central lawn having a new-ish lobby that's a perfect space for enjoying 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 are 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 have the ability to spot this rustic yellow farmhouse using 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 (that has cooked at legendary hotels and restaurants throughout Italy) and Lois Freedman (obama and CEO from the legendary Jean-Georges restaurants all over the world). You cannot go wrong with 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 been owners of go-to NYC brunch spot Penelope – to spread out Shindig in the heart of Woodstock. The inviting, casual space (a mixture of booths, small tables, and stools in the bar) seats as much as 30 people and touts a menu that's focused on comfort food like tomato soup, the Shindig burger (featuring an addictive, smoky sauce), grilled cheese, and banana pancakes. They can have a coffee takeout window should you just need a pick-me-up among hiking or shopping. Closed on Mondays and Tuesdays, they're open for supper, dinner, and weekend brunch.

Phoenicia Diner

Just 20 minutes west of Woodstock is that this first-come, first-serve diner that's so famous that there are often a line snaking into the parking lot during busy weekend brunch hours. There's plenty of back yard to savor the new 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 much more. If you're a fan of brunch cocktails, make sure to order the Bloody Mary. Want a preview of the menu? You can buy the Phoenicia Diner Cookbook co-authored by the diner's chef, Chris Bradley, to test 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 a wide 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. Perfect for a unique night out (entrées start at $24), you'll love both fancier vibe indoors and also the more casual vibe in the backyard 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 single 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 is the kind of place where the staff is on a first-name basis with locals and may discuss book recommendations about any genre all day long. Together with Woodstock Book Fest, the bookstore has hosted events featuring Pulitzer Prize winners, along with 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

Just Fifteen minutes south of Woodstock is the gorgeous Ashokan Reservoir, that is among the streams that provides NYC its drinking water. You will find a variety of trails that lead to the reservoir, but the promenade is a straightforward, almost 3-mile walk that provides the very best views of the Catskill mountains. It's paved and flat so it's great for walkers and bikers (and it is 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 in the private residence (a.k.a. it's closed towards the public outside of show hours) from the late Levon Helm who Rolling Stone once called “rock 'n' roll's greatest drummer.” Helm originally started performing these concerts in his home studio to raise extra cash to help with medical bills from throat cancer in the early 2000s. Now operated by volunteers, the legacy from the Midnight Ramble continues with various artists who've included Billy Bob Thornton, Norah Jones, Elvis Costello, Garth Hudson, yet others. Make sure to grab your tickets online (they're not sold in the door), and a reusable metal or plastic cup with the beverage of your choice (rosé, anyone?) as cans/bottles aren't allowed around 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's the North American monastic seat of the Gyalwa Karmapa Ogyen Trinley Dorje, the top 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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