For most of the 20th century, the town of Woodstock, NY was known as a hippie Mecca; a place where suit-wearing city dwellers could swap ties for tie-dye, where music and art flowed freely, and where the weekend flea market smelled of patchouli and weed.
And then came the juice bars.
As a new wave of weekend visitors became residents, they brought with them innovative ideas for what the Woodstock could be: sophisticated and modern, with an appreciation of arts and culture—but perhaps less partial to tie-dye. Sure, Woodstock will always draw peace, love, and Dylan devotees. But there’s no denying that in recent years the town has evolved faster than you can say, “The festival didn’t happen here.”
With world-class dining, tasteful wine and cocktail bars, and next-generation boutiques, here’s how to experience a perfectly un-hippie weekend in today’s Woodstock.
Friday
Check into one of Woodstock’s two new boutique hotels situated in the thick of it all. Woodstock Way is a rustic-chic hotel situated beside Tannery Brook’s waterfall, offering an array of contemporary comforts from luxe beds to in-room massage therapy. The design blends upstate-rustic aesthetic and global flair (think exposed beams and wide-plank flooring adorned with kilim rugs and sheepskins), in a style that we’re rapidly coming to recognize as Modern Catskills.
The Herwood Inn is a newcomer that aims to meet the needs of modern travelers on a holistic level, with locally made honey and toiletries in each suite and an online concierge via in-room tablet devices. Stretch out those long-trip kinks using yoga mats available to each guest. In concept, this four-suite inn is an homage to the great female musicians of the 20th century (think Joni and Aretha), but you’ll find little evidence of that trope beyond the in-room record players and vinyl collections. The design here is the perfect intersection of modern bohemian meets minimal with geometric textiles, subway-tiled bathrooms, macrame wall hangings, and happy plants for a splash of green. (Curious about other newcomers on the local lodging scene? Read our article on 4 new upstate hotels.)
After you’ve dropped your bags and spun some vinyl, head down Mill Hill Road to A&P Bar for dinner and drinks. If the name seems oddly familiar, it’s because, yes, it’s coined after the chain grocery store that once took up shop there; locals have long referred to the building as “the old A&P”, and the name aptly stuck. Start with a cocktail like the Bitter Me Bourbon (with apple and vanilla bitters, among other ingredients) or the Opus 39 (Gin, Meletti Amaro, Aperol, and Cinzano Bianco with apple and lavender bitters) before digging into hearty dishes like shepherd’s pie, made according to an old English recipe, and with a side of sautéed & Dijon-creamed Brussels sprouts.
If you’re feeling up for lighter fare or want to bar hop on your way to dinner, head to Early Terrible, a hip new wine and tapas bar that offers a list of curated wines from the West Coast and Europe, as well as artful cocktails, in a rustic, moody atmosphere; dim lights, lounge music, and antique décor set the chill vibes.
Saturday
Next door to Early Terrible you’ll find the Mud Club, a coffee and bagel joint to help you wake up and get your Saturday rolling. Choose from a variety of espresso drinks, drip coffees, or nitro cold brew to pair with a wood-fired bagel, stuffed bagel balls, or brekkie sandwich on a croissant. (On Fridays and Saturdays from 5-9pm, the same oven also dishes up wood-fired sourdough pizza.) From there, you’ll be ready to peruse the walkable shops along Tinker Street. The Golden Notebook is an indie bookstore with something for everyone, including a section on local authors and history. A tome about Woodstock’s surprising history would make an unforgettable souvenir; so would a locally made bar of soap or a bottle of maple syrup from the newly opened Baird's General.
At Three Turtle Doves you’ll find vintage women’s clothes and accessories, many from luxury designers, meticulously selected to create a high-end boutique vibe. For the fellas, there’s Changes—a clothing and accessory store with quality-yet-casual attire.
When lunchtime rolls around, enjoy casual Mexican cuisine at Tinker Taco Lab, a laid-back spot known for its avant-garde tacos and tamales made with fresh ingredients and gourmet flavors; pork confit and fried avocado tacos are popular choices. Then treat yourself to a salted chocolate chunk cookie or an ice cream sandwich from the artisanal Overlook Bakery.
Walk off lunch at Opus 40, Harvey Fite's immersive sculpture park in nearby Saugerties, open May through November, where you’ll stroll among—and upon—acres of intricate bluestone mosaics, sculptures, walls, and paths. Or, try a moderate hike up Overlook Mountain where you’ll be rewarded with stunning views from atop a fire tower (4.6 miles roundtrip).
Head back to the hotel to relax, freshen up, and make your reservation for dinner at Silvia, a restaurant passionate about sustainability that serves organic, locally sourced dishes. Try the authentic Bibimbap, the house burger, or gourmet salads; don’t pass over desserts like lavender pots de crème. For something a little more grab-and-go, Dixon Roadside is a newcomer by the owners of Phoenicia Diner serving locavore comfort food.
If there’s a show that night at the Colony, you’re in luck. This intimate venue, in an iconic former hotel, puts you up close to a range of up-and-coming, local, and nationally acclaimed live acts. But it's far from the only place to see a show. The recently revamped Bearsville Theater is back open with a lively roster of music, and newcomer Pearl Moon is bringing local talent to the stage along with full breakfast, lunch, and dinner menus.
Sunday
Sundays are for brunch, and the caramelized banana pancakes at Shindig are a decadent treat. Those who prefer savories can choose from a small menu of wraps and scrambles.
Before hitting the road, take a quiet stroll through the Woodstock Artists Cemetery to pay respect to those who have contributed to the rich artistic legacy of the region. The preserved area includes intricately designed bluestone grave markers to serve as reminders of Woodstock’s countless contributions to the arts over time.
