Congratulations! You’re spending the day (or two, maybe more) in Woodstock, legendary for its arts and music, beautiful surroundings, and open-hearted, eclectic humans. The town that famously did not host the 1969 Aquarian Exposition but did, in fact, inspire it. The place where fascinating people have been taking breaks from city life for well over a century. Your interest in being here demonstrates your good sense. Here’s some local knowledge to help guide your footsteps to places you’ll love:
Woodstock’s individualist, creative, and quirky excellence is applied to the art of making visitors feel at home. Find a favorite among these and you’ll never want to leave, except for the fact that there’s so much to explore—and you’ll be welcomed back to your well-appointed lodgings for more chill time with fresh memories to savor.
HOTEL DYLAN For truly immersive Woodstock memories, stay at a hotel that’s true to its roots. The Hotel Dylan specializes in bohemian sophistication; you’ll find updated hippie iconography sprinkled through the property, a record player in your room and a library of vinyl discs to spin, two fire-pits, and a slammin’ Mexican restaurant on-site. thehoteldylan.com
WOODSTOCK WAY HOTEL takes a slightly different tack, emphasizing sustainable construction and operation. And you’ll love The Tannery, their common area with waterfall views and prints of iconic musical moments. Treat yourself to some beverages as well as locavore and vintage goodies displayed for sale. woodstockway.com
THE WOODSTOCK INN ON THE MILL STREAM has a 1,000-foot stretch of rushing rocky riverbed on three acres of lush, landscaped sanctuary in the heart of town: an exquisite retreat steps away from all sorts of adventure. Beautifully appointed, comfy lodging options range from standard rooms to cottages, bungalows, and a house. woodstock-inn-ny.com
At GLASCO WOODSTOCK, you can stay in an exquisite mid-18th-century home with 30-foot ceilings and vast windows looking out on Overlook Mountain, while enjoying design-forward, meticulous luxury hospitality and a hot tub under the stars. stayglasco.com
THE NEST AT WOODSTOCK If you like to glamp, The Nest at Woodstock offers a two-acre private site with a spacious and luxuriously appointed safari-tent bedroom as well as a cozy, rustic-fabulous camping kitchen.
ORIOLE 9 features a superb breakfast/brunch menu served all day long. Go light with avocado toast or a smoked salmon bagel, or all in with brioche French toast, Huevos Rancheros, or Eggs Hemingway: you’ll be good to go for that hike. oriole9.com
THE YUM YUM NOODLE BAR, another longstanding local fave, offers five varieties of healthy noodles to choose from and enhance with your choice of four broths and eight different proteins, plus plates large and small and bento boxes for kids and grownups. yumyumnoodlebar.com
CUCINA offers elegant Italian in a beautifully restored farmhouse—you can opt to eat around the big table for 24 if you like, or on the wraparound porch—with a Roman Pizza Garden on weekends. All three are vegetarian-friendly and emphasize fresh and local (this is, after all, Woodstock). cucinawoodstock.com
COLONY WOODSTOCK Enjoy yummy food at their high capacity, outdoor, socially distanced beer garden with food, drinks, and amazing music to keep your feet tapping while you enjoy your meal. Some of our favorites are their smooshburger, pulled pork sandwich, and Colony cobb salad. colonywoodstock.com
It’ll be hard to resist the dessert menus at those places; we do not recommend you try to do so. But for that extra touch of sweetness, say a mid-afternoon or evening pick-me-up, Woodstock has your back with these exceptionally sweet choices.
NANCY’S OF WOODSTOCK ARTISANAL CREAMERY has just relocated to a bigger spot, so now there’s spacious seating both indoors and out where you can enjoy the handmade, fresh-churned ice creams, along with homemade donuts to munch or take home. nancysartisanal.com
EJ BONBONS & CONFECTIONS was co-founded by two Michelin-star-trained chefs who see chocolate as a medium for high art, from the look to the flavor and mouth-feel. Passion fruit? Raspberry dark chocolate? Mix and match, my friends! ejchocolates.com
At OVERLOOK BAKERY you can find brownies and biscotti and more; try a stuffed Moonrise Bagel or order up a stunning custom cake garnished with edible flowers. facebook.com/overlookbakery
At TIBETAN ARTS AND CRAFTS you’ll find stunning rugs that can make a room; brilliantly colored, flattering, flowy clothing; jewelry ranging from statement pieces to subtle sterling concoctions; and Tibetan ritual crafts like Buddhas and mandalas. tibetanartsncrafts.com
At J BLISS STUDIOS, a husband-and-wife team of fine artists handcrafts custom pieces in gleaming precious metals and sparkling gemstones alongside their line of greeting cards, drawings, and decor. jblissstudios.com
SUNFLOWER NATURAL FOODS MARKET has loads of just that—good clean organics perfect for provisioning your picnic—but they also stock the latest in holistic beauty and body-care items, from creamy lotion potions to potent supplements and homeopathic remedies for whatever ails ya, and they’re experts in all of it. You’ll also find wonderful Hudson Valley handcrafted gifts here. sunflowernatural.com
IMMUNESCHEIN TEA HAUS AND GIFT SHOP has organic loose-leaf tea, exclusive handcrafted ginger elixirs, tea ware, and accessories, along with other locally made products and gifts; come get some wellness-to-go and enjoy a ginger shot and a cuppa in their outside seating space. immune-schein.com
PEGASUS FOOTWEAR specializes in both classic and up-to-the-minute styles, with a broad selection to choose from and old-school personal service. They’ll get you properly shod for any and every occasion.
And don’t miss a stop at HEADSTOCK & CO., “A Curated Headshop for the Discerning Customer,” where you can find local gear and memorabilia among the artisanal paraphernalia. headstockandco.com
HOUST & SON is the local indie hardware-and-more, thriving since 1932 thanks to Woodstock’s “tinkers and makers, DIYers and dreamers, gardeners and campers, cooks and geeks,” as they like to say. housthardware.com
WOODSTOCK LIGHTING LAB is a place to shop for DIY lighting kits, lamp parts, fixtures created from up-cycled materials, reclaimed and found objects. If you’ve got a project underway, they’ll consult with you on a lighting plan—and they’ll fix and refurbish your favorite lamp to perfection. woodstocklightinglab.com
OVERLOOK MOUNTAIN offers a moderate 4.6-mile climb, mostly up a disused gravel road, to a summit with spectacular vistas and a lot of fun exploration: there’s a ruined hotel and a fire tower for view enhancement, and the remnants of a crashed plane, although that takes some hunting. Leashed dogs are welcome.
WOODSTOCK GOLF CLUB features a challenging 18 holes made exciting by good design around the Sfawkill Creek, rock ledges, ponds, and stately trees. It hosts what may be the longest-running tournament in American golf, the Woodstock Open. It’s a private club—albeit refreshingly influenced by scores of artistic members over the decades—but bring them your out-of-town driver’s license and hotel receipt, and you’ll be welcomed like a native. woodstockgolf.com
WOODSTOCK ARTISTS ASSOCIATION AND MUSEUM Over a century old, yet as fresh as it gets, Woodstock Artists Association and Museum hosts a permanent collection of more than 2,000 works and a variety of dynamic exhibits and programming. woodstockart.org
At the CENTER FOR PHOTOGRAPHY AT WOODSTOCK you’ll find a vital hub for dialogue and discovery in photography and related media in ongoing workshops and lectures—as well as a collection of more than 1,800 contemporary photographs collected over 40 years. cpw.org
Don’t miss the gallery exhibitions at the KLEINERT/JAMES CENTER FOR THE ARTS at the WOODSTOCK BYRDCLIFFE GUILD: one of the earliest utopian arts colonies in America. You’ll find stunning works by new and emerging artists in the Byrdcliffe Shop, plus a cornucopia of programming. woodstockguild.org
THE WOODSTOCK SCHOOL OF ART offers workshops, weekly studio classes, and online classes in the fine arts. Classes are open to all, with no entrance requirements or experience necessary, part of a Woodstock tradition of free expression coupled with a solid technique that’s well over a century old. woodstockschoolofart.org
COLONY WOODSTOCKis as authentic as it gets, from the beer garden to the ballroom and back. Dine outdoors while savoring some of the region’s best live music (if the weather’s bad, the party moves inside.) Come join an Open Mic and you’ll forever be able to say you played Woodstock. colonywoodstock.com
OVERLOOK BICYCLES offers rentals both right in town and at the Ashokan Rail Trail for your exploring pleasure, sales and service, and Saturday morning group rides with fresh-roasted small-batch coffee thrown in. overlookbicycles.com
THE VILLAGE GREEN is the place to people-watch, make friends with strangers, listen to an impromptu jam session, or play some chess. Drum circles happen every Sunday. Impromptu fun? Come help make some.
Love Woodstock? Think you may have found your special place? Here are some folks who’ll be happy to help you figure your logistics:
HUDSON VALLEY PROPERTIES - BERKSHIRE HATHAWAY will bring their vast local knowledge and expertise to bear to make your home-search painless and fruitful; plus, they’ve got a full suite of relocation services to comb out any tangles. bhhshudsonvalley.com
ULSTER SAVINGS BANK is a 170-year-old hometown treasure, a mutual savings bank (no stockholders to fatten), and winner of the 2019 Banky Award from the Institute for Extraordinary Banking for their top-notch philanthropy, customer service, thought leadership, internal culture, and financial literacy education. ulstersavings.com
ECHOSIXTY6 will help you re-root your transplanted business or grow a fresh one. They’re Woodstock-based and city-skilled creatives, marketing experts, and digital services specialists who take pride in an easy-going collaborative approach to simplifying whatever your brand may be. echosixty6.com
MANAGE THIS HOME If you own an elegant place up here, and would like to share it with others when you’re not using it yourself, Manage This Home offers turn-key Airbnb management services that will keep your property pretty , pristine, and protected, and will ensure your guests stay happy during their entire visit. managethishome.com
CATSKILL CONCIERGE offers home maintenance, property management, personal services from pet care to holiday light hanging, and help organizing anything from a massage to a dinner for 24, as well as management of restoration and renovation projects. catskill-concierge.com