The historic town still rocks.

By Gary Chetkof and Marika Romero


8 a.m. breakfast

Ahh, it’s the weekend in Woodstock and that means we can head to our favorite bagel shop, Moonrise Bagels, for their unique New York style water bagels, stuffed with all sorts of things including bacon, egg and cheese—and the best cup of coffee in town (especially their cold brew coffee in the summertime). 

9 a.m. dog walk 

Time to walk the dog. We head to The Comeau Property with Tiger, where dog lovers converge to walk their pups through the beautiful and serene woods, along streams and swimming holes. A good place to meet up with friends and to make new ones.

noon art galleries

It’s time to visit all the fantastic shops, art galleries and eateries. There’s the WAAM (cultural center) for great visual art that reflects Woodstock’s heritage as an arts colony; Changes (my favorite men’s retailer); Castaways for wonderful vintage clothing and accessories; Clouds Gallery (incredible glass blown vases and objets d’art) and Candlestock for one-of-a-kind candles (which make great gifts with a Woodstock flavor).

1:30 p.m. Lunch

For a great sandwich on the go, Woodstock Meats is it for us. It’s also the place to pick up grass-fed local beef and chicken, baby back ribs and fresh seafood. For a nice sit-down meal with outdoor seating right in the middle of town there’s Pearl Moon, Yum Yum Noodle Bar, the vegetarian Garden Café, as well as the Millstream Tavern that’s located at the Woodstock Golf Club overlooking the flowing stream. 

5 p.m. Happy Hour

Time to stop in at Early Terrible for a hand-crafted cocktail in a special outdoor setting with fire pits and natural rock tabletops, right off the main road in town. The rustic, incredibly decorated inside bar reminds us of a treehouse. Great place to people-watch and meet tourists from around the world. For a more local crowd reflective of Woodstock and its diversity, we head to Station Bar & Curio where we can also play some pool. 

6 p.m. Dinner

Last count, Woodstock’s host to more than 40 eateries. But our favorite three are Good Night for Asian fusion, Medo for upscale Sushi and The Red Onion for mussels, steaks, burgers and salads. 

9 p.m. music

Woodstock’s known, of course, for its music scene, and there are essentially three places to take that in: Bearsville Theater presents national bands in a 500-capacity room, while Colony is homier and presents emerging artists. Pearl Moon features local and regional bands and attracts more of the local scene.


8:30 a.m. hike

We head out with Tiger for a nice scenic hike up Overlook Mountain where we plan for a three-hour hike that’s more challenging and provides amazing views of the Hudson Valley. But first, we stop at Sunfront Farms market for a green juice and either a Papaya Maya or a Starburst shake, as well as some nuts and healthy snacks for the sure-to-be long trek. For a less adventurous hike, we head to the Rail Trail, which is right outside of Woodstock, off Route 28 in Hurley, and wraps around the Ashokan Reservoir. Either way, a perfect way to begin your day 

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