Although the famous festival that borrowed the town's name actually took place about an hour west at what is now the Bethel Woods Center for the Arts, the spirit of the 1960s and early 1970s is still alive in Woodstock, New York. Peace, love, understanding, art, and music still reign in this quaint village nestled in the Catskill Mountains. Here is a guide to spending a fun-filled weekend in Woodstock. 

Originally published 05/01/2019


5 pm: Get to know Woodstock on wheels

Gain your bearings in this town by exploring it on wheels. Rent a bike at Overlook Mountain Bikes and hit the trails. You won’t want to bring your bike back until sunset.

8 pm: Grab dinner at Silvia

A person holding a large burger with fried crab
Credit: @silviawoodstockny on Instagram

As you watch the chefs in the open kitchen prepare your New American dishes like lemon ramp risotto, chicken schnitzel, and grilled lamb chop, imagine what this place might have been like in the 1970s. Before it was Silvia, the spot was home to a famous dive bar called Joyous Lake, which entertained legends like The Rolling Stones and Muddy Waters back in the day. The building was abandoned for more than a decade before sisters Betty and Doris Choi revitalized the space with Silvia.


9 am: Fuel up at Bettina Phoenicia

Fuel up for your day in nearby Phoenicia and enjoy classic dishes made with fresh, locally-sourced ingredients, many of which are grown at Bettina’s own farm up the road. You're spoiled for breakfast choices with a menu that features buttermilk pancakes, Creme Brulee baked French toast, a breakfast taco skillet, delicious pastries, and more!

11 am: Explore the great outdoors

Rolling hills of the Catskill Mountains seen beyond the crisp blue waters of Ashokan Reservoir
Credit: @lovely.lady.lens on Instagram

Spend the day outside in nature. Warm up with an easy stroll around Ashokan Reservoir, a 2.7-mile paved walkway along the reservoir that supplies 40% of New York City's drinking water. More than 100 years ago, a dozen different communities were relocated in order to build the reservoir, which is why you'll see many historical signs around the area stating "Former Site of...". Graduate onto the Overlook Mountain path, which is a little more than two and a half miles—all uphill—and offers stunning views of both the Hudson Valley and the Catskills. Along the hike, you'll pass by some grand ruins of resorts from the early 1800s, when the first tourism boom from Manhattan began.

1 pm: Stop for lunch at the Phoenicia Diner

A photo of a spread of food from Phoenicia Diner: a burger, toast with baked beans and sausage, french toast with strawberries, bacon, and coffee
Credit: @newyorksherpa on Instagram

Phoenicia Diner is as famous for its food as it is for being a magnet for Instagram influencers. You won't be able to resist snapping a photo of your meal or dessert on the aesthetically pleasing placemat that doubles as the menu. As with many places you'll encounter this weekend, ingredients are seasonal, fresh, and locally sourced.

2:30 pm: Prepare to be amazed by The World's Largest Kaleidoscope

Kaatskill Kaleidoscope at Emerson Place 105

Admit it, your curiosity is piqued. When at the diner, you're just a 5-minute drive from the World's Largest Kaleidoscope at Emerson Resort & Spa, so pop on in! For $5, watch a ten-minute show in the refurbished farm silo accompanied by sound and music. Believe it or not, you'll get the best view if you lay down on the floor. Wander through the various shops and buy your own (smaller) kaleidoscope, puzzles or plushies for the kids, or locally-made soap and beauty products.

3 pm: Go Shopping

A white sign that says "Tinker Street" in black font with a list of shop names underneathC
redit: @pamelamini on Instagram

Tinker Street is all about shopping, with everything from rugs and furniture to unique clothing on offer. You'll find your typical tourist shops with tie-dyed t-shirts and novelty items, but also some spots with unique home goods, where you'll find items like a pillow embroidered with RGB or gorgeous pottery made locally in town. Don't miss a stop at Peace, Love & Cupcakes, which has won competitions on Food Network for its sweet offerings and where the cupcakes are named after beloved musical artists from the 1960s and '70s.

4 pm: Admire exciting exhibitions at The Center for Photography at Woodstock 

The Center for Photography at Woodstock

In 1977, New York City gallery owner Howard Greenberg founded this nonprofit exhibition space, where visitors can enjoy rotating shows and speakers. Located in the heart of Woodstock, this building once housed Cafe Expresso, where Bob Dylan, Joan Baez, and other musicians performed in the 1960s.

5 pm: Enjoy Italian cuisine at Cucina

This small Italian restaurant is housed in an old wrap-around farmhouse. Cucina serves wonderful pizza and pasta dishes on a beautiful outdoor patio surrounded by greenery.

7 pm: Catch a live show

Woodstock Playhouse - Photo Courtesy of Woodstock Playhouse

One of two venues owned by the Byrdcliffe Arts Colony (among the country’s first utopian arts communities), the Byrdcliffe Theatre always has something good going on, from exhibitions to live music to workshops. Make sure to check the performance schedule. The Woodstock Playhouse and Colony also have weekly performances worth checking out.


9 am: Have a wood-fired bagel at The Mud Club

Morning bun pastry from the Mud Club in Woodstock, New York

Open at 9am Friday-Sunday, The Mud Club has wood-fired bagels and sandwiches in a Tolkien-esque building with a nicely landscaped outdoor seating area. Keep in mind that if you're coming from New York City, these bagels may be a little smaller than you're used to, so order two or add in a morning bun (pictured) if you need a fuller meal.

11 am: Stroll through Opus 40

Opus 40 environmental sculpture in Saugerties, New York

Just 10 minutes from Woodstock is Opus 40, a magnificent 6.5-acre environmental bluestone sculpture built from an abandoned quarry. Harvey Fite, the sole creator of this walkable sculpture park, used only hand tools to fit together thousands of stones to form a series of terraces, ramps, and steps, to serve as a showcase for his sculptures. 


By train or bus:
Woodstock is not easily accessible by rail, but Trailways bus lines make regular stops in downtown Woodstock, with service from New York City, Albany, Newburgh, and more.

By car:
From Albany: 1 hour
From New York City: 2 hours
From Philadelphia: 3 hours
From Boston: 3 hours, 30 minutes
From Montreal: 4 hours, 30 minutes

By plane:
Woodstock is located about one hour by car or bus from both Albany International Airport and Stewart International Airport

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