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What to Do Over a Weekend in Woodstock, NY

For city-dwellers, Woodstock, NY makes the perfect weekend escape from the urban grind. It’s a short two-hour drive from New York City, and less than four hours from Boston. This small town is world-famous for its music and arts scene (although, be warned, the Woodstock concert was actually held in nearby Bethel, not in Woodstock itself), and offers outdoor pursuits, innovative dining, and plenty of culture. Here’s what to do if you have a weekend to spend in Woodstock, NY.


When you arrive, take some time to explore the town and get your bearings. The area is extremely walkable, so leave your car in one of the plentiful (and free) street parking spots or the municipal lot, and head out on foot. There’s plenty of quirky shops to satisfy all of your shopping needs—even if you’re not in a buying mood, crystal shops like The Turquoise Lady and Dharmaware will help you get a feel for the local Woodstock flavor.

Next, squeeze in some culture at the Woodstock Artists Association and Museum, which showcases local artists. Afterwards, head to the beautifully-designed Woodstock Playhouse for a show.

Once you’re ready for dinner, grab a table upstairs at Joshua’s Cafe and Restaurant—tables by the window offer some great views of the passerby below. This restaurant has a Middle Eastern slant—get one of the entrees that come with the Middle Eastern appetizer plate and add falafel for a dollar—you won’t regret it.

If you’re in the mood for a nightcap, your options are limited—many places close fairly early in Woodstock. Venture a little bit off the main strip to the Havana Club at the Woodstock Lodge, which is open until 3AM on the weekends, and offers the best crowd and music.


Assuming you didn’t hit the Havana Club too late last night, rise and shine bright and early this morning to beat the breakfast crowd at Oriole 9. Like most eateries in Woodstock, Oriole 9 is very vegetarian-friendly—try the excellent and hearty Tofu Hash. Add a double shot of espresso to power you up for your next challenge—Overlook Mountain.

About a 15-minute drive outside of town, the parking lot for Overlook Mountain is located across from the Karma Triyana Dharmachakra Tibetan Buddhist Monastery. The unique temple and grounds are worth a quick look, before you tackle the mountain. (The Monastery also has bathrooms available to hikers in exchange for a suggested monetary donation if you need a rest stop.) The hike to the top of Overlook Mountain is 2.4 miles each way, but it’s up an easy, wide dirt road (albeit with a steep incline.) Be sure to stay on the trail—the signs warning of rattlesnakes are accurate—on a hike in August, we saw a few rattlesnakes lurking in the underbrush off of the path. Near the top, there’s an interesting abandoned hotel. Explore at your own risk—there are plenty of rattlesnakes in here, and the stone walls are unstable.



At the summit, you’ll be rewarded with another climb—a fire tower with seven flights of stairs. If you make the ascent, the viewing platform offers incredible views of as far away as the Hudson River and Westkill Mountains, as well as detailed signage so you can tell what you’re looking at. Take in even better views from the ledge behind the old Ranger Station before heading back down.



Now that you’ve worked up a sweat, cool down at one of the nearby swimming holes, like the The Big Deep before heading back into town.

Continue your outdoorsy day by dining outside at the Garden Cafe’s delightful outdoor courtyard. Top off the night with a drink at the Harmony, which offers live music most nights and amazing people-watching every night.




Grab a late brunch at Bread Alone, locally famous for its Brioche French Toast with apples and maple syrup. Wander through the town square—you may see the town’s political activism alive and well in the form of a protest. Stick around town for the afternoon so that you can catch the 4pm Sunday show at Maverick Concerts. Before you leave town, if you haven’t had enough sugar for the day, be sure to grab a scoop of Jane’s Homemade ice cream from Taco Juan’s (and one of their surprisingly good espressos to keep you awake on your drive home.)



Where to Stay

Immerse yourself in the Woodstock aesthetic by staying at the newly renovated Hotel Dylan. This property has some serious design cred, thanks to the services of Robert and Cortney Novogratz (you may recognize them from their HGTV show, Home by Novogratz.) The hotel’s 11 rooms each feature unique artsy touches like a Elliott Landy music print, a vinyl record player and records, and a Michael de Feo tie-dyer flower print.

At night, guests gather around the Hotel Dylan’s communal fire pit, and roast S’mores or pop jiffy-pop over the fire the old-fashioned way. On nice Friday evenings in the summer, there’s an outdoor movie night for guests. The 1972 restored VW bus parked on the property adds to the Woodstock vibe that makes this hotel stand out amongst the rest in town. Rates start at $189 per night and include a continental breakfast.



(Photo: TripAdvisor, LLC)

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