The most famous small town in America, Woodstock is a historic haven for artists, musicians, visionaries, and reformers – a place to relax and take in all that nature has to offer.  Nearby outdoor activities are a big part of why Woodstock has continued to attract newcomers, offering those coveted Instagram-friendly experiences—a trip to a local swimming hole, a sunset kayak trip, or a dinner at a vegan outdoor restaurant.


Woodstock’s music and artist community flourished way before rock legends such as Bob Dylan, The Band, and Janis Joplin began living in or spending time in the Catskills.  Nestled under the impressive Overlook Mountain, Woodstock’s scenic mixture of nature and the arts have always attracted creative spirits and unique individuals – from early settlers and bohemian artists to sixties rock ‘n’ roll heroes, to today’s Sunday Drum Circle.  The town has always fostered a tight-knight community that supports the arts and local business, fiercely protecting the environment and their independent way of life.


Once known for its head shops and rocker bars, Tinker Street has a fresh new look with shops, restaurants, and lodging that feel upscale but have enough of a bohemian vibe to make you feel at home.

If you ask around, people here might tell you that Woodstock was built on creatively charged rocks, alluding to the fact that artists are drawn here cosmically, for its geographical mysticism. This fact alone is enough to intrigue any creative person to consider Woodstock a lovely place to live, work, play, + create. 


Woodstock is home to The Karma Triyana Dharmachakra Buddhist monastery, situated beautifully at the top of Mead’s Mountain Road.


Hollywood on the Hudson? Right off Rock City Road, there’s a cemetery dedicated to memorializing Woodstock artists and luminaries. Buried here are 20th-century painters Philip Guston and Milton Avery, American folk and bluegrass songwriter John Herald, children’s author Paula Danzinger and Howard Koch, co-writer of Casablanca.

Our Woodstock directory geographical area starts at Thruway Exit 19 and continues West along the Route 28 commercial corridor.  Here you’ll find car and motorcycle dealers, gas stations, seasonal businesses, furniture and home decorating stores, even a CBD shop.  You’ll pass Gourmet Row, a delightful collection of a delicious cheese shop, gourmet take-out and a well-stocked liquor store.  A few miles up, you’ll turn right at the 2nd traffic light onto Route 375 where you’ll drive past Hannaford’s grocery, a gas station and a few businesses until you come to Route 212 where you’ll arrive at the doorstep of the most famous small town in America – Woodstock, NY.


From there, we travel west (left) along Mill Hill Road/Route 212, which includes small shops, our beloved Playhouse and an assortment of small eateries, shops and restaurants.  Mill Hill turns into Tinker Street at the Village Green, which is the heart of Woodstock.  From there we travel north to Overlook Mountain and west into the hamlets of Bearsville, Shady, and Lake Hill, with treasured shops, music venues, restaurants and galleries to explore.  Our directory ends on a crescendo after we turn right at the Bearsville Complex to arrive at Cooper Lake, one of the area’s most treasured attractions. We refer you to our Woodstock Map below for an artist’s representation.

Garden Cafe Woodstock NY
Inside+Out Woodstock Map

Jason O’Malley


Connecting You to Woodstock



Have an account?