Little Black Book

Beyond the Festival Legend: The Best of Woodstock, New York

by California Chaney
Land Land of Love. Photo by local Woodstock photographer Kit Chaney.

The Woodstock '50 festival may be cancelled, but the spirit of the Summer of 1969 lives on in the most famous hippie mountain town in America.

WOODSTOCK, New York — This year marks the 50th anniversary of the legendary Woodstock, a three-day festival of music and peace that changed rock and roll history forever and defined a generation of hippies, lovers, and rebels. Of course, the festival didn't actually take place in the town of Woodstock, but 43 miles south in Bethel, NY. Why not Woodstock, you ask? Because after a second, third, and fourth attempt to secure a venue, time ran out, and festival founder Michael Lang settled on Max Yasgur's 601-acre dairy farm. It was too late to change the posters, so the organizers simply kept it Woodstock Arts and Music Festival.

Truth be told, the music and artist community of Woodstock flourished way before Lang, with rock legends such as Bob Dylan, The Band, and Janis Joplin living in or spending time in the Catskills before anyone had even conceived of the festival. The "give peace a chance" revolution rang true through the mountain town, which became a hotbed where artists created music and art of the counter-culture. Today, the influx of creative minds remains alive and well, with farm-to-table restaurants, sustainable hotels, and organic cider farms popping up and making Woodstock, well, pretty groovy. With the help of local photographer , here's how you can create your own 2019 festival feelings.

Silvia
Photo courtesy of Silvia.

Where to Eat and Drink


1 Tinker St.; +1-845-684-7091
A local hang serving organic, farm-grown comfort food and good vibes. Located directly across from the town square and bus drop-off, they serve breakfast until 3 p.m. due to their popular "Upstate" fried egg sandwich on a homemade buttermilk biscuit. Closed on Mondays.


6 Old Forge Rd.; +1-845-679-3600
A vegan, organic, and GMO-free cafe and juice bar with a beautiful outdoor garden patio. Closed on Tuesdays.


42 Mill Hill Rd.; +1-845-679-4242
The newest rock star to hit the town of Woodstock, Silvia is family-run and -owned by Brooklyn-born Korean sisters Doris and Betty Choi and their husbands. Everything from the vegan kimchi to miso fish sauce is made in-house, with locally sourced veggies and organic meat provided from over twenty local farms. Cozy up near the wood-fired grill and peer into the open kitchen as you sip a cocktail infused with fresh-picked berries.


Woodstock's latest hideaway — where you won't find the typical tie-dyed homage to hippie culture — is a restored barn capturing the essence of the mountain town.


101 Tinker St.; +1-845-810-0203
This 1900s converted railroad train station hasn't always lived in Woodstock. Originally built by the Ulster & Delaware Railroad Company, the station operated as Brown's Station until 1954 when operations stopped. Seeing a "for rent" sign, a Woodstock local purchased the abandoned station in 1970 and transported it on a flatbed truck, spending four decades sitting on it until he finally built his dream bar for his family and friends. The station isn't just any old bar: The decor nods to its bygone era, with original signs, lumbar, timetables, and station lamp posts. Open seven days a week with live music Friday and Saturday nights.

43 Mill Hill Rd.
A funky new cafe on the town's main road serves wood-fired bagels, pastries, and coffee seven days a week. Go early in the morning on the weekends before their homemade pretzels sell out.


109 Mill Hill Rd.; +1-845-679-9800
Situated in a restored farmhouse, the restaurant serves contemporary Italian cuisine made from local and seasonal ingredients. There's outdoor seating on a large wraparound porch. In the winter, cozy up to the indoor fireplace room with a 24-person communal dining table. Open every day with brunch on Saturdays and Sundays.

Grandfather Woodstock greeting visitors to town. Photo by Kit Chaney.

Where to Shop


62B Tinker St.
Local vintage store for flow-y dresses, handbags, jewelry, and accessories. Open on Saturdays and Sundays.


Tinker St.
An eclectic shop for vintage and new home goods, gifts, candles, sage, and other local herbs. Open daily.


33 Mill Hill Rd.; +1-845-684-0463
Hoping to find some rockin' tie dye? This is your shop for all things Woodstock memorabilia: handmade glass pipes, CBD, and Bob Marley posters included. Open every day.


33 Tinker St.
A BYO store for refillable cleaning, beauty, and other sustainable household products to encourage shoppers to lower their waste consumption and stop using single-use plastic. (If you like the sound of that, check out Tabootoystore's favorite plastic swaps for travel.) Closed Mondays and Tuesdays.


Maple Lane
A family-run outdoor flea market that has been widely attended for more than 40 years. You can find everything and anything from antiques, vintage postcards, cooking supplies, and artwork. Open on Saturdays and Sundays behind the BreadAlone coffee shop.

Opus 40 Sculpture Park. Photo by Kit Chaney.
Westwind Orchard. Photo courtesy of Westwind Orchard.

What to Do


83 Mill Hill Rd.; +1-845-393-4325
A multidisciplinary health and wellness center for body, mind, and spiritual work in a beautiful, light-filled space in the heart of town. They also offer film screenings, lectures, and workshops all year.

The secluded, jade-colored swimming lagoon where hippies of generations past shed their clothes on hot days to bathe in fresh, mountain-stream water and cannonball from the rope swing. Fifty years later, it remains so popular that a permit is now required 24-hours before visiting. You can purchase one at the police dispatch in town at 76 Tinker St. for ten bucks. Both the Big Deep and sister swimming hole, Little Deep, can be located via Google Maps and both have roadside parking areas.


353 Meads Mountain Rd.
A 4.6-mile moderate hike with beautiful wildflowers during the blooming seasons and multiple lookout points. Accessible all year round for hiking, snowshoeing, and dog walking (with leashes).


Rt. 23A, Haines Falls, NY
Cascading down 260-feet, the Kaaterskill Falls, one of the most popular destinations in the Catskills, are breathtakingly beautiful to visit at any time of year. Located off of Route 23A in Haines Falls (twenty miles from Woodstock), the trail is 1.4 miles roundtrip with a view of the falls above you as your reward. It can be slippery and steep, so hikers are advised to wear supportive hiking shoes.


50 Fite Rd, Saugerties, NY
A six-acre outdoor earthwork sculpture garden and museum five miles from Woodstock in the town of Saugerties has sweeping views of the Catskill Mountains. Visitors can walk through and around the property's subterranean pathways and nine-ton monolith that is the epicenter and summit of the sculpture garden. Open from May to November on Thursdays through Sundays. Tickets are $10 for adults.


215 Lower Whitfield Rd, Accord, NY; +1-845-626-0659
Fabio Chizzola and his wife, Laura Ferrara, purchased this 32-acre apple orchard in 2002 and have since turned it into a revived organic oasis — raising honeybees, pears, plums, cherries, garlic, herbs, and winter squash. They run a farm store producing and selling boozy cider. Following their Italian roots, the couple transforms the orchard into a pizzeria on the weekends, where you'll find master pizza maker Cicco slinging pies in a wood-fired oven using organic produce sourced from the orchard (of course). Weekly events with small plates and tastings take place on the large lawn with picnic tables. Babies and dogs welcome. Closed Tuesdays and Wednesdays.

Woodstock Way. Photo courtesy of Woodstock Way.
Hotel Dylan. Photos courtesy of Hotel Dylan.

Where to Stay


10 Waterfall Way, +1-845-684-5911
Tucked behind a flowing waterfall, the newly re-opened Woodstock Way is a twelve-room contemporary hotel deeply routed in the music and arts community that put Woodstock on the map. Situated on the site that was once an 1800s tannery, the revitalized property utilized reclaimed wood and low-carbon footprint materials to create a rustic-chic oasis, drawing guests close to nature, yet steps from the action in town.


320 Maverick Rd.; +1-845-684-5422
For the design-crazed travelers, look no further than hippie-chic Hotel Dylan. Sitting on Route 28 across from the Ashokan Reservoir, the eleven-room boutique hotel is itself a music and arts colony, just like the festival 50 years ago, with rooms named after Jimmy Hendricks and Van Morrison with album covers and instruments lining the warm and bright walls. An outdoor fire pit is set for late-night jam sessions and the Sante Fe Mexican restaurant continues the good vibes with killer margaritas.

How to Get There

Woodstock is easily accessible by car, bus, or train and is about two-and-a-half hours from NYC. By car, take I-87 N to 28 W. Hourly buses are available with and drop you off right in the center of town. To access via train, take the Metro North to Kingston and then hop on a local bus for a twenty-minute ride to town.

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