NEWSLETTER
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. Woodstock is home to the nation’s oldest arts and crafts colony, Byrdcliffe, dating back to 1903, as well as Maverick Concerts, home to the oldest chamber music festival in America. Here is a guide to spending a fun-filled weekend in Woodstock.
Originally published 05/01/2019. Updated 3/2/2026.
FRIDAY
4 pm: Settle in
Nestled creekside just steps from town, the Woodstock Way Hotel sets the scene for an eco-luxe escape that will ground you in nature and immerse you in upscale treehouse living. Settle into an oversized guest room carefully curated in its decor and layout, also offering a private balcony and deck.
6 pm: Dinner at SILVIA
Credit: @silviawoodstockny on Instagram
As you watch the chefs in the open kitchen prepare your New American dishes like steelhead trout, chicken schnitzel, grilled lamb chop, and local mushroom & pasta, imagine what this place might have been like in the 1970s. Before it was SILVIA, a family-owned restaurant that connects food and people with back-to-basics cooking, 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.
8 pm: Grab a Drink at Small Talk Woodstock
Right in the heart of town, Small Talk is an intimate yet chic cocktail bar and the perfect nightcap. Settle in for an expertly crafted cocktail or divine glass of wine.
SATURDAY
9 am: Fuel up at Bettina Phoenicia
Start 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, crisp tofu hash, taco skillet, huevos rancheros, delicious pastries, and more!
11 am: Explore the Outdoors
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. Move 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: Lunch at the Phoenicia Diner
Credit: @newyorksherpa on Instagram
Phoenicia Diner is as famous for its food (and appearance in the hit show Severance) as it is for being a magnet for Instagram influencers. You won't be able to resist snapping a photo of your meal on the picture-perfect placemat that doubles as the menu. As with many places in Woodstock, ingredients are seasonal, fresh, and locally sourced. Try the mouthwatering biscuit & gravy, jalapeno popper stuffed hashbrowns, french toast, or smoked trout on a bagel.
2:30 pm: Check out The World's Largest Kaleidoscope
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
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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 embroidered pillows 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: Visit Karma Triyana Dharmachakra
Set against the beautiful backdrop of Overlook Mountain, this vibrant and serene Tibetan monastery serves as a retreat and study center, open for the public to appreciate and explore the main grounds, main shrine, bookstore, or take a weekend tour.
5:30 pm: Enjoy Italian at Cucina
Set in a charming restored farmhouse with a wrap-around porch, Cucina brings classic Italian dining to Woodstock. The menu features seasonal, locally sourced ingredients to create crispy flatbread pizzas, handmade pastas, and entrées ranging from pan-seared trout to chicken parmesan and grilled ribeye steak. In the warm weather, you can dine al fresco on the outdoor patio.
7 pm: Catch a Show
There is no shortage of art and entertainment in Woodstock. The Bearsville Theater is an exceptional and unique setting for artists from around the globe to perform to an audience in an intimate, acoustically perfect auditorium. Byrdcliffe is a center for the arts that always has something good going on, from exhibitions to live music to workshops. Make sure to check the performance schedule. For even more music, dance, theatre, and film check out The Woodstock Playhouse calendar. And for nightly local entertainment, Colony is the place, also home to a popular seasonal “In The Garden” concert series.
SUNDAY
9 am: Wake up to Moonrise Bagels
The savory stuffed bagel concoctions at Moonrise Bagels are what foodie dreams are made of. Bite into bacon, egg, and cheese baked right into a warm handmade bagel, or go for a pastrami Reuben, buffalo chicken, or eggplant parm stuffed bagel packed with flavor in every bite. There are also vegan and vegetarian stuffed bagel options. If you’re a bagel purist, traditional bagels and cream cheeses are always on deck.
11 am: Stroll through Opus 40
Just 10 minutes from Woodstock lies Opus 40, a magnificent 6.5-acre bluestone sculpture built from an abandoned reclaimed quarry at the foot of Overlook Mountain. Created solely by artist Harvey Fite using only hand tools, this walkable sculpture park of carefully fitted stones, terraces, ramps, and steps is enveloped by 63 acres of meadows, forested trails, and historic buildings. The venue hosts a lineup of concerts, nature walks, workshops, and wellness classes.
GETTING THERE
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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