Woodstock, NY

Were it not for its rich cultural pedigree, and its connection (however tenuous) to the festival of the same name, Woodstock might resemble any other charming Upstate New York town. But, beyond the Village Green, where tourists gather and old hippies still strum guitars, lies a treasure trove of galleries, restaurants, shops, and theaters.  

Driving time from Poughkeepsie: 50 minutes


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courtesy of bread alone

10 a.m.

Hippies tend to sleep late and, in Woodstock, though hipsters have largely replaced the old guard, the laid-back hippie vibe prevails to this day. So, stop for breakfast before touring the town. At Bread Alone, enjoy a hearty breakfast burrito or a tree-hugger’s favorite, avocado and sprouts on organic ciabatta. 


11 a.m.

Walk toward town and check out the shops, like Candlestock, which offers a gorgeous selection of beeswax, drip, and handmade candles; The Freewheel Pottery, which has a fabulous selection of beautiful, well-priced jewelry, handbags, art, accessories, and more; and The Golden Notebook, a town fixture for four decades (we hear it was one of Bowie’s favorite shops). 


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1 p.m.

If you’re a vegan (or not), you’ll enjoy lunch at the bright, cheerful, puppy-loving Garden Café, where you can dine outdoors in (of course) the lovely garden, weather permitting.


Photo by Dion Ogust

3 p.m.

Head to Rock City Road, which has lots of nooks, crannies, and a smattering of shops, including Tibetan Arts & Crafts. Wend your way around to the other side of Tinker Street for more shopping, and stop at the Village Green, where you’re sure to find some characters — maybe even Allyn Richardson, aka Grandpa Woodstock — hanging out. 


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5 p.m.

Woodstock’s arts scene goes beyond music, and galleries abound in the area. Do not leave without visiting the Byrdcliffe Arts Colony, the country’s oldest (built in 1902) operating Arts and Crafts colony, with 30 unique buildings of the motif, all in a bucolic setting.





More to Explore:

Woodstock is a hiker’s Xanadu, so, if you don’t mind rattlesnakes (seriously), consider the Overlook Mountain Hike. Also, Bob Dylan’s footprints are all over the town, and landmarks are plentiful, among them Big Pink (right), the house where he and The Band recorded the seminal Basement Tapes.

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