Woodstock

Woodstock, NY, nestled in the Catskill Mountains, is a charming, bohemian town known for its artistic vibe, natural beauty, and rich cultural history. Though often associated with the iconic 1969 Woodstock Festival, the event took place in nearby Bethel. Still, Woodstock retains the spirit of that era, serving as a hub for music, art, and outdoor activities.

Whether you’re looking for a peaceful retreat or a culturally rich experience, Woodstock has something for everyone. This guide highlights the best places to stay, eat, and explore in this unique town.

How to Get There

From New York City:
Woodstock is roughly 100 miles north of NYC, making it an ideal weekend getaway. The trip takes about two hours by car, depending on traffic.

Transportation Options:

• By Car: The easiest way to reach Woodstock is by driving. Take I-87 North (New York State Thruway) and follow Route 375 to the town.
• By Bus: Trailways offers service from NYC’s Port Authority to Kingston, about 20 minutes from Woodstock. From Kingston, a taxi or ride-share will get you there.
• By Train: Though no direct train reaches Woodstock, you can take Amtrak from Penn Station to Rhinecliff, then arrange a 30-minute taxi or ride-share to Woodstock.

Getting Around:
Woodstock’s town center is walkable. For nearby hiking spots like Overlook Mountain or the Ashokan Rail Trail, a car is useful, though bikes are popular during warmer months.

Where to Stay

Woodstock offers a variety of accommodations, from cozy inns to boutique hotels.

• Hotel Dylan: Just outside town, this retro-inspired boutique hotel offers rooms with a ’60s vibe, plus access to a saltwater pool and Santa Fe Woodstock, a beloved local restaurant.
• Woodstock Way: Located near a creek and just steps from the town center, this eco-friendly hotel offers modern amenities with rustic charm. Private cabins provide a peaceful retreat.
• Twin Gables of Woodstock: A historic bed-and-breakfast operating for over a century, Twin Gables offers uniquely decorated rooms in a cozy setting, close to shops and restaurants.

Accommodation Tips:
If you want easy access to shops and restaurants, stay near the town center. For a quieter experience, consider staying on the outskirts or in nearby towns like Saugerties or Kingston.

Things to See and Do

Woodstock offers a range of activities, from outdoor adventures to art and culture.

Explore Mill Hill Road:
The town’s main street is perfect for a leisurely walk, lined with local shops, galleries, and restaurants showcasing Woodstock’s eclectic personality.

Mowers Flea Market:
Operating since the 1970s, this weekend flea market offers antiques, local crafts, and vintage goods, giving you a chance to mingle with locals.

Shop at Local Boutiques:

• Mirabai Bookstore: Specializing in spirituality, wellness, and metaphysical topics, this peaceful shop offers books, crystals, and gifts.
• Everyday Magic: An enchanting shop with handmade goods, jewelry, and unique souvenirs.
• Candlestock: Known for its drip candle mountain, this shop lets visitors watch candles create a colorful wax sculpture.

Relax at Glo Spa:
After a day of exploring, unwind at Glo Spa with massages, facials, and wellness treatments.

Outdoor Adventures

• Overlook Mountain: This 5-mile round-trip hike offers scenic views and historical interest, with ruins of an old hotel and stunning panoramas from the fire tower.
• Kaaterskill Falls: A short drive from Woodstock, this easy hike leads to one of New York’s tallest waterfalls, offering breathtaking views.
• Ashokan Rail Trail: This 11-mile trail, perfect for walking, biking, or running, provides scenic views of the Ashokan Reservoir and surrounding mountains. It’s flat and accessible for all skill levels.

Where to Eat and Drink

Woodstock boasts a diverse selection of dining options, ranging from farm-to-table restaurants to casual diners.

• Bread Alone
  This organic bakery and café is a favorite among locals and visitors alike. It offers fresh bread, pastries, and organic coffee.
• Cucina
  Located in a beautifully restored farmhouse, Cucina serves Italian-inspired cuisine made with local ingredients. The outdoor seating area is particularly lovely during warmer months.
• Silvia
  Known for its farm-to-table dishes, Silvia features a modern, rustic setting with a focus on sustainability. The menu includes creative small plates and craft cocktails.
• The Woodstock Pub
  For a more casual dining experience, head to The Woodstock Pub, where you can enjoy hearty pub fare and local beers in a relaxed environment.
• Phoenicia Diner
  A short drive from Woodstock, this diner is a hotspot for its retro vibe and updated takes on classic comfort food.
• Tinker Taco Lab
  This food truck is a local gem, serving inventive tacos made with fresh, locally sourced ingredients.
• Good Night
  A newcomer to the dining scene, Good Night offers an Asian-fusion menu in a cozy, intimate setting.
• Santa Fe Woodstock and Abandoned Hard Cider (at Hotel Dylan)
  After a day of exploring, unwind with Mexican cuisine at Santa Fe Woodstock or sample a local cider at Abandoned Hard Cider.

Seasonal Highlights

Each season in Woodstock brings its own unique charm and activities.

• Fall:
  The town is especially picturesque during fall, with vibrant foliage and crisp air. It’s an ideal time for hiking and attending seasonal festivals.
• Winter:
  In winter, nearby Hunter Mountain offers excellent skiing and snowboarding. Woodstock itself becomes a peaceful, snowy retreat.
• Spring:
  Springtime in Woodstock is perfect for those who want to experience the natural beauty of the area without the summer crowds.
• Summer:
  Summer is the best time to enjoy outdoor concerts, art fairs, and hiking. The town is bustling with visitors, and the weather is ideal for outdoor exploration.

Travel Tips for Different Types of Travelers

• For Art Lovers:
  Woodstock has long been a haven for artists. Be sure to visit local galleries like the Woodstock Artists Association & Museum (WAAM).
• For Nature Enthusiasts:
  Hiking, biking, and exploring waterfalls are must-do activities. Don’t miss Overlook Mountain and the Ashokan Rail Trail.
• For Foodies:
  The town offers a wide variety of dining options, from farm-to-table meals to international cuisine and local specialties.
• For Group Trips:
  Woodstock is an excellent destination for group trips, whether you’re planning a girls’ weekend or a family reunion. The variety of activities, from spa days to hiking, ensures that everyone will find something enjoyable.

Practical Information

• Best Time to Visit:
  While Woodstock is a year-round destination, the best times to visit are during the fall for the foliage or summer for outdoor festivals.
• Budget:
  Woodstock accommodates various budgets. You can choose from affordable inns to luxury boutique hotels, and dining options range from casual eateries to fine dining.
• Local Customs and Etiquette:
  Woodstock is a laid-back, artsy town. Respect the local environment and make sure to support the town’s many small, independently-owned businesses.

3-Day Itinerary

Day 1: Exploring Woodstock

• Morning: Stroll down Mill Hill Road and visit local spots such as Mirabai Bookstore and Candlestock.
• Afternoon: Check out the Mowers Flea Market for unique finds and vintage goods.
• Dinner: Enjoy casual tacos at Tinker Taco Lab.

Day 2: Outdoor Adventures

• Morning: Hike Overlook Mountain for stunning views and explore the old hotel ruins.
• Afternoon: Head to Kaaterskill Falls for a short hike to one of New York’s tallest waterfalls.
• Dinner: Try the cozy Phoenicia Diner for a hearty post-hike meal.

Day 3: Relax & Unwind

• Morning: Walk or bike the peaceful Ashokan Rail Trail.
• Afternoon: Relax at Glo Spa with a rejuvenating treatment.
• Dinner: Finish your trip with a meal at Bread Alone, known for its fresh, locally-sourced dishes.