Even though the eponymous 1969 music festival didn’t actually take place in Woodstock (that honor goes to the nearby town of Bethel), this small upstate New York town is full of a counter-culture, bohemian spirit unlike any other. Disney World has hidden Mickeys, Woodstock has peace signs, and they’re just about everywhere you look. Made out of twigs, emblazoned on flags or graffitied on fence posts, the town proudly displays its music history. But Woodstock isn’t just about rock n’ roll, although there’s plenty of vintage band tees and tie dye to be found—it’s also a town that boasts a picturesque main street home to exceptional restaurants, world-famous cupcakes and plenty to explore off the main drag.
Read on for my weekend guide to exploring Woodstock, New York.
This Labor Day, Zach and I were searching for a weekend getaway that wasn’t an airplane ride away, and I stumbled upon Escape Brooklyn, a blog dedicated to New Yorkers on the hunt for an upstate adventure. That’s where I discovered that Woodstock is only a 2.5 hour Trailways bus ride away—especially key since car rental prices had skyrocketed for the holiday. The bus was easy enough and conveniently drops you off in the center of town.
(Note: It wasn’t until we arrived in Woodstock that we heard about LINE, Trailways’ venture into the business class experience. This new bus line connects NYC to major Upstate locations like New Paltz, Phoenicia, Hunter and yes, Woodstock, with amenities like premium WiFi, snacks and onboard hosts. We’re definitely going to try it next time we head upstate.)
Where to stay
Thanks to Escape Brooklyn, I had read about Woodstock Way‘s Lone Wolf cabin retreat. So I was pleasantly surprised when I learned they were opening a hotel on Labor Day weekend…and there were still rooms available. I immediately booked us into a King room and we were blown away when we arrived. The property is organized into separate cabin buildings, made out of reclaimed wood with living roof systems. The attention to detail is impressive—our room featured a turntable (of course) with vinyls curated by a local artist, heated bathroom floors and the plushest of Brooklinen towels. Combining that with an expansive outdoor deck overlooking the Tannery Brook Waterfall made it an idyllic weekend retreat.
The best part? Woodstock Way is located in the heart of town within easy walking distance of everywhere you need to go, but is set back far enough from the street that it feels private and out of the way. Talk about the best of both worlds.
Things to do
Take the time to walk up and down the main street, popping into every store. Woodstock isn’t big enough to feel shop ’til you drop, so it’s worth perusing the town’s stores. And everything is local, from the quaint and cozy home goods at Shop Little House to the sustainable refill store Bring Your Own. Aside from these two, our favorite shops were The Golden Notebook, a bibliophile’s haven, and Woodstock Socks (self-explanatory). There’s also a bustling flea market each Saturday and Sunday off Deanies Alley and Maple Way, just behind Bread Alone.
If music and vintage band posters are your personal brand, you won’t run out of options here. Woodstock Legends was especially stocked with the best 1960’s hippie memorabilia you can find.
For a full two day Woodstock visit, dedicate one day to shopping and exploring the town, and the other to hiking Overlook Mountain. You can do both in one (long) day, but it’s best to split into two to really see what the town has to offer and to allow yourself a moment to relax after the steep uphill incline of Overlook.
The Overlook hike has many draws, thanks to the Overlook Fire Tower and an ideally placed cliff face that provides panoramic views of the Hudson Valley. But if you know me and my love of true crime, you could guess that my favorite sight was the ruins of the Overlook Mountain House. The hotel was first built in the early 1800s, and this is its third and final iteration that’s crumbling into ruin. Explore with caution—the mountain is a timber rattlesnake habitat, so watch where you step.
Where to eat
Woodstock is a foodie’s paradise. While the town isn’t overrun with restaurants, every one holds up to the snobby Manhattan dining scene. Grab tacos at Tinker Taco Lab or a burger with fried Brussels sprouts at Shindig. For a sweet tooth, try the Food Network-acclaimed cupcakes at Peace Love & Cupcakes or grab a scoop of ice cream at Nancy’s. Our favorite breakfast spots were Shindig (okay confession time, we ate here three times in one weekend, it’s that good) and Bread Alone—it opens earlier than anything else at 7 AM so you can get your coffee and pastry fix in before Shindig opens its doors. For those with dietary restrictions, there are plenty of vegan options to choose from, starting with the Garden Café with its sunny patio.
But dinner is where Woodstock really shines. Woodstock restaurants pride themselves on using local, seasonal ingredients, and nothing shows that off better than the steak and summer succotash at Silvia. Another standout? Cucina, an Italian restaurant housed in a restored farmhouse, has an ambiance most often found in five-star Charleston restaurants, with a pale, earth toned color palette, warm lighting and a welcoming bar. The service and food is unfussy but never boring—I had a simple rigatoni with sausage, peas and cream that rivaled the famous see-and-be-seen Bar Pitti’s signature dish.
New Yorkers and out of towners alike, don’t sleep on Woodstock. It’s an upstate experience that’s truly special.
Looking to explore more outside the city? Check out my guide to Long Island’s North Fork region here!