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Family Fun Weekend in Bearsville, NY Itinerary

Last updated: 2024 Jun 14

Woodstock Rock n’ Roll History & Pizza Delight

Morning

Start your day with a delightful breakfast at the famous Garden Cafe on the Green, known for its fresh and organic dishes. After breakfast, immerse yourself in the music history of the area with the Woodstock Rock n’ Roll History Tour. Learn about the legendary Woodstock Festival and the iconic musicians who have graced this town.

Afternoon

For lunch, head to Woodstock Pizza Theater for a unique dining experience with delicious pizza. Afterward, enjoy a relaxed afternoon exploring the town on your own. Visit the local shops and galleries, or take a leisurely walk around the charming streets of Woodstock.

Evening

In the evening, savor a family dinner at Cucina Woodstock, known for its Italian cuisine and cozy atmosphere. After dinner, take a stroll and enjoy the vibrant and artistic nightlife of Woodstock.

Bedtime

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Woodstock Rock n’ Roll History Tour
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Scavenger Hunt Adventure & Farm-to-Table Delights

Morning

Enjoy a hearty breakfast at Oriole 9, a popular spot for its farm-fresh ingredients. Then, engage in a fun-filled Woodstock Scavenger Hunt. Explore the town in a unique way as a family, solving clues and discovering hidden gems.

Afternoon

For a true farm-to-table experience, have lunch at Sunfrost Farm Market & Juice Bar. Taste the freshness of local produce in their delicious dishes. After lunch, take a short drive to visit the animals and enjoy the beautiful surroundings at a local farm or petting zoo.

Evening

Indulge in a memorable dinner at The Little Bear, known for its cozy ambiance and delectable menu. After dinner, you can enjoy some family-friendly evening entertainment, such as a live music performance or a movie night at a local venue.

Bedtime

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Woodstock Scavenger Hunt
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Nature Walks and Creative Cuisine

Morning

For your last day, start with a relaxed breakfast at Bread Alone Bakery & Cafe, a favorite spot for its artisanal bread and pastries. Then, spend the morning exploring the natural beauty of the area. Take a family-friendly hike in a nearby park or nature reserve, enjoying the fresh air and scenic views.

Afternoon

Have a leisurely lunch at Red Onion Restaurant, known for its diverse menu and welcoming atmosphere. After lunch, engage in a creative activity as a family, such as a pottery class, a painting session, or a visit to a local art studio.

Evening

End your family weekend with a special dinner at Bear Cafe, a iconic restaurant in Bearsville. Enjoy the unique and artistic setting, reflecting the spirit of the town. After dinner, take a relaxing evening walk and cherish the memories of your time together in this charming location.

Bedtime

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