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Exploring the Charming Woodstock, New York

Exploring the Charming Woodstock, New York Itinerary

Last updated: 2024 Jun 14

Discovering Woodstock's Charm

Morning
Start your day with a delicious breakfast at Oriole 9, known for its fresh and locally sourced ingredients. Afterward, take a leisurely stroll through the Woodstock Village Green and explore the unique shops and galleries.
Afternoon
Head to Overlook Mountain for a scenic hike and breathtaking views of the Hudson Valley. After working up an appetite, enjoy a late lunch at Tinker Taco Lab, where you can savor creative and flavorful tacos.
Evening
Indulge in a delightful dinner at The Bear Cafe, known for its farm-to-table cuisine and cozy atmosphere. Afterward, catch a live performance at the Bearsville Theater, a renowned venue for music and entertainment.
Bedtime
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Local Delights and Artistic Vibes

Morning
Start your day with a cup of coffee and a pastry from Bread Alone Bakery. Then, visit the Woodstock Artists Association & Museum to admire the works of local artists.
Afternoon
Enjoy a leisurely lunch at Garden Cafe on the Green, a charming spot with a beautiful garden setting. Afterward, explore the Woodstock Byrdcliffe Guild, a historic arts colony that showcases contemporary art and crafts.
Evening
For dinner, savor the flavors of Mediterranean cuisine at Cucina, known for its delicious Italian dishes. Afterward, head to The Colony Woodstock for live music performances and a vibrant nightlife experience.
Bedtime
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Woodstock's Culinary Delights

Morning
Start your day with a hearty breakfast at Phoenicia Diner, a retro-style diner known for its classic American comfort food. Afterward, explore the Woodstock Playhouse, a historic theater that hosts a variety of performances.
Afternoon
Enjoy a leisurely lunch at The Red Onion Restaurant & Bar, which offers a diverse menu featuring American and international cuisine. Afterward, visit the Woodstock Museum, where you can learn about the town's rich history and cultural heritage.
Evening
Treat yourself to a memorable dinner at Shindig, a farm-to-table restaurant that emphasizes locally sourced ingredients. Afterward, relax and unwind at The Guilded Otter, a brewpub known for its craft beers and scenic outdoor seating.
Bedtime
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Exploring Nearby Saugerties

Morning
Take a short trip to Saugerties and start your day with a delicious breakfast at Mirabellas. Afterward, visit the Opus 40 Sculpture Park & Museum, where you can admire the impressive stone sculptures and explore the beautiful landscape.
Afternoon
Enjoy a leisurely lunch at Love Bites Cafe, a cozy spot known for its creative sandwiches and homemade desserts. Afterward, explore the Saugerties Lighthouse, a picturesque landmark located along the Hudson River.
Evening
Head back to Woodstock for dinner at The Pines, a contemporary American restaurant with a focus on seasonal ingredients. Afterward, unwind with a cocktail at Woodstock Brewing, a local brewery offering a variety of craft beers.
Bedtime
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Culinary Delights and Shopping

Morning
Start your day with a delicious breakfast at Olive's Country Store & Cafe, a charming spot known for its homemade baked goods and gourmet pantry items. Afterward, explore the unique shops and boutiques in Woodstock, such as Tinker Street Emporium and The Golden Notebook.
Afternoon
Enjoy a leisurely lunch at Sylvia, a cozy cafe known for its homemade soups and sandwiches. Afterward, visit the Woodstock Farm Festival, where you can browse local produce, crafts, and artisanal products.
Evening
For a delightful dinner, head to Yum Yum Noodles, a popular spot for Asian fusion cuisine. Afterward, enjoy a relaxing evening at The Colony Cafe, a laid-back venue that hosts live music performances and open mic nights.
Bedtime
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