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The little town at the foot of the Catskills may be best known for giving its name to the 1969 music festival (which, fun fact, actually took place in Bethel, about 45 miles away). Now, on the 50th anniversary of the fest, there are plenty of reasons to visit besides hippie nostalgia. Here’s how to spend a rustic, artsy, food-filled weekend in Woodstock, New York.

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woodstock new york airbnb
Airbnb

1. Stay in a cabin, barn or tree house

You’re in the Catskills, shouldn’t your lodging reflect that? The area has no shortage of options to help you live out your rustic (but not too rustic) dreams, like a barn with a hot tub, a tree house overlooking a pond or a farmhouse with a yoga studio. Don’t be surprised if your rental comes with a little history, as many of them were once residences for the artists and writers who flocked here.

woodstock new york overlook mountain house
Sinisa Kukic/Getty Images

2. Hike up to an abandoned hotel

The trail to Overlook Mountain House is one long, uphill dirt road, but it’s absolutely worth the climb. At the top, you’ll find the eerie ruins of a resort that was once a turn-of-the-century Catskills vacation hot spot. After more than a few misfortunes (it burned down twice), the property was turned over to the state in 1940, leaving behind its empty arched doorways and stairways to nowhere for the exploring.

woodstock new york fire tower
Carolyn Stanley

3. Climb the fire tower

We didn’t send you all the way up there just to see one thing. Walk a little farther past the ruins and you’ll reach the summit, which boasts a historic 1927 fire tower you can still climb for 360-degree views of the Hudson River, the Catskills and beyond. Before heading back down the trail, follow the short path to a flat rock ledge on the other side, where you’ll find yet another breathtaking vista.

woodstock new york r and r taproom
Lily Brown

4. Sip craft beers and natural wines

The living-room vibes at R&R Taproom are ideal for a post-hike drink. Owner and certified beer sommelier Megan Reynolds curates a rotating selection of brews, available in five-, eight- and sixteen-ounce pours. (We recommend a bunch of small pours for a DIY flight.) If you’re hungry, dig into fancied-up bar food like guac-loaded nachos or a Beyond burger topped with pickled beets.

woodstock new york woodstock playhouse
Woodstock Playhouse/Facebook

5. Catch a show at the playhouse

The Woodstock Playhouse isn’t your average small-town theater: Founded in 1938 by Woodstock native and industry vet Robert Elwyn, it has hosted scores of performances featuring major names (Diane Keaton, Estelle Parsons, Chevy Chase). It even hosted a concert series in 1968 that may or may not have inspired a certain music festival the following year. 

6. Have an Italian feast

Sure, you can get pasta back in the city, but how often do you get to eat it in an adorable yellow farmhouse? Head to Cucina, grab a seat (on the porch if the weather is nice) and fill your table with wood-fired pizzas (like the Caprina, with fig-rosemary spread, goat cheese, pear, arugula and truffle oil) and pastas (the rigatoni with sausage, peas and spicy tomato is a must).

woodstock new york downtown
dlewis33/Getty Images

7. Wander along the main drag

The town’s hippie spirit is still very much alive, as evidenced by the many peace signs on display on Tinker Street, the main thoroughfare. Pick up a new read or two at the Golden Notebook, admire the artists’ work at the Center for Photography at Woodstock and browse quirky homewares at Shop Little House. On weekends through November, pop by Mower’s Flea Market for goods like vintage jewelry, seasoned cast-iron pans and various crystals (complete with an explanation of your chosen stone’s powers—this is Woodstock, after all).

8. Drink in an old train station

You might be feeling more of a stay-in-and-read-by-the-fire vibe during your trip, but if you want to go out, Station Bar & Curio is the place to be. Built in 1900, this authentic train station has lived in three different Catskill towns. Today it’s a lively watering hole complete with board games, a pool table and frequent live music.

9. Eat some really good bread

You may have seen Bread Alone’s organic loaves at farmers markets in the city, but it’s worth trying them straight from the source. The specialty here is naturally leavened breads (including several types of sourdough), but you can’t go wrong with the bagels or pastries either. For something more substantial, sit down for breakfast and lunch fare like the “salmon works on rye” or a spicy roasted cauliflower sandwich.

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