My knowledge of Woodstock, NY has long been limited to a combination of prejudice and hope: I watched clips and seen photos of the legendary festival and have since imagined the streets of the town to be walked by long-haired hippies in acid-magenta flannel shirts with guitars and smokes in their hands. Knowing how urban culture evolves over time I couldn’t leave those thoughts unproven, so I headed up to Woodstock to explore the scene.

Entering the town, one immediately knows they are in Woodstock

Long fought for liberal values present themselves in the signs like these
I stopped by at Bread Alone, a charming bakery serving excellent espresso and sandwiches

The Tea Shop serves soothing blends from Harney & Sons and other brands

Grace Tokyo is a hat shop — designer and owner lives in Tokyo and sends out the latest hat designs to Woodstock

Some of the hats are beyond creative, in any sense of that word

Colony is Woodstock’s primary music and event venue, or as the locals call it “The Smartest Rendezvous in The Catskills”

Upcoming performances at Colony

Shindig, a minimal lunch spot

Old Spokes Home is a bike shop and a non-profit with a most wonderful sense of humor

The Golden Notebook, Woodstock’s only general bookstore

Woodstock General Supply offers design goods and minimal basics

Shop Little House is my favorite discovery — filled with a well-curated selection of new and vintage goods, books, and a record player that is actually plying records

Owner of Shop Little House Jojo Ans

A step out, and I’m reminded that I’m in Woodstock

Another wonderful discovery — Pacama Handmade offering a minimal selection of hand-crafted furniture and locally made home goods

Owner of Pacama Handmade Cedric Martin

One of the world’s most charming police stations is located in Woodstock

D-DAY is an avant-garde concept store — owners Asa and Jodi have collaborated on custom-made leather goods, textiles and jewelry

D-DAY label

Woodstock amuses with city details, like this pavement section handmade by an artist

Buy for now, Woodstock

Getting to Woodstock, NY

Bus: Approx. 3 hours | $60 round trip (See schedule)
Car: Approx. 2 hours

Thanks for reading! If you enjoy city details, check out my series of photo journals: there’re 3 issues so far: Hudson, NY; San Francisco, CA; and Red Hook, NYC.

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I'm designer, photographer, and professional flâneur with a peculiar love towards impeccable design, well-crafted stories, and the intricacies of urban life. Follow me in the field on Instagram, read my tidbits Twitter and Facebook and subscribe to my weekly culture newsletter.