HVGuide
The Best Restaurants & Bars In Woodstock
photo credit: JN Silva
Contrary to popular belief, the legendary music festival didn’t take place in Woodstock, New York, but that doesn’t stop people in tie-dye from flocking to this Catskills town every year. That, combined with the recent influx of city folk, means that you’ll find live music and excellent food at pretty much every restaurant and bar in town.
Most of the spots on this list are on Tinker Street (the main stretch in town), so it’s easy to hit up a bar or grab lunch after browsing shops filled with novelty candles and vinyl records. Woodstock is also less fussy than a lot of other fancy-schmancy Hudson Valley towns, so you can walk into dinner straight after your afternoon hike or farm tour and blend right in with the crowd. Start your weekend in the mountains with a few tacos and a margarita, have some seasonal Italian food on a wraparound porch, and end the evening in an old train station-turned-bar where you can play pool on a large patio.
THE SPOTS
We've been to this Southeast Asian spot on a Monday night and seen parents share walnut larb and grilled trout while their kids doodle in coloring books, but you're just as likely to come and see a someone kicking off a birthday trip in the Catskills with 10 of their closest friends. This is the duality of Good Night, a restaurant with really delicious drinks that’s good for any occasion. Order some fried local oyster mushrooms with a tangy yuzu aioli and the monkfish tempura that’s bright and crisp without tasting too oily or heavy.
photo credit: Silvia
The first thing you’ll see when walking into Silvia is the roaring fire at the center of the open kitchen. Fire is a recurring theme in the dishes, too, with wood-fired pita, smoked beets drizzled with charred jalapeno chimichurri, and a 14-ounce steak that outshines pretty much every other piece of beef we’ve eaten in the Catskills. The food is really well done, and a night here is a surefire way to impress a date or persnickety parents. The creamy artichoke soup is a local favorite for a reason—the herby starter is topped with sunchoke crisps and has the faintest kick of spice.
If the idea of the L’Artusi of Upstate New York is exciting to you, then you should make it a priority to go to Cucina. And if it’s not, then we’re curious and a little nervous to hear what does excite you. The seasonal Italian food, converted farmhouse, and wraparound porch make this place easily one of the best dinners you can have in the Hudson Valley—and its the ideal backdrop for a romantic meal with your partner after a day of lounging around your Airbnb.
Oriole 9 has inspirational quotes written on chalkboards and a big vegan menu—in other words, it’s not the spot to bring someone who you’re trying to convince that Woodstock isn’t all tie-dye and Birkenstocks. But it is the place to bring someone who wants a great burger, bucket of fried chicken, or huevos rancheros. They also have Balthazar pastries in the morning, which somehow taste better here in Ulster County than in Soho next to people selling “original” film scripts.
Bread Alone's sourdough is a staple in New York's fancy loaf scene, but they have also have brick-and-mortar cafes sprinkled around the Hudson Valley. The location in Woodstock is small, but it’s a good stop for coffee and a pastry. Their other locations are in Kingston and Rhinebeck, if one of them suits your weekend getaway better, and all of them have things like specialty chocolate and small-batch jam.
The Mud Club is the perfect morning stop for coffee and some bagels. The space is basically a gorgeous Hudson Valley backyard to lounge and play in, with a bunch of benches and giant rocks where you can spend a couple of hours planning an afternoon hike or your inevitable move Upstate. The wood fired bagels are impressive on their own, but we always find ourselves ordering the Tinker Tuesday BEC that comes with house tomato jam and horseradish aioli.
In Woodstock, you’ll find the political conspiracy theory hippie, the artisan jewelry-making hippie, and the Garden Cafe hippie, who’s posted up at this spot on Old Forage Road. This place makes really good vegetarian and vegan food, and it feels authentic to the Woodstock spirit without being kitschy. While a lot of the dishes include meat substitutes like tofu or tempeh, there are also vegetable-heavy plates that won’t make you miss meat at all (like the spinach basil pesto pasta and the portobello panini). Go for brunch or dinner, and sit in the outdoor area if it’s nice out.
This funky-looking wine bar and small-plates spot is from the same team as Mud Club (and located right next door). It’s the perfect place to sit and drink outside with someone you do coupley things with. Get a spot next to the fire pit (if you don’t mind your clothes smelling like beef jerky the next day), or hang out inside under the disco ball. If you want to snack on something, we like the dips that come with crunchy Mud Club bagel chips that you won't be able to stop eating. Just know they're only open Thursday through Sunday.
photo credit: Anne Cruz
This intimate bar is where you should have pre-dinner drinks after a day of shopping for produce and small-batch seed butters at Woodstock’s weekly farmers market. The short cocktail menu includes a fantastic pickled pepper martini and a mezcal drink spritzed with absinthe, plus small bites like dolma and plump slices of kielbasa. Small Talk is also open until 11:30pm, which is a lot later than most spots in town. Keep that in mind for the next time you return from a hike later than you expected and need to regain your strength with a drink, charcuterie board, and chicken pot pie.
Station Bar has a pool table, a jukebox, and a fairly large outdoor area with tables where you can drink a beer that was made somewhere in New York. The last time we were here, we discovered our new favorite reggae artist, got invited to a pool party, and met a man named Clark who goes to Station Bar nearly every night. It’s quite possible you’ll meet Clark, too.
