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Enchanting 5-Day Trip to Sleepy Hollow Itinerary

Published: 2023 Oct 08

Exploring the Legends

Morning

Start your day with a hearty breakfast at The Barn at Sleepy Hollow. Afterward, immerse yourself in the local legends by visiting the Philipsburg Manor, a historic site that offers a glimpse into the 18th-century life. Don't miss the Old Dutch Church, the final resting place of Washington Irving, the author of "The Legend of Sleepy Hollow."

Afternoon

For lunch, head to The Twisted Oak in Tarrytown, where you can enjoy a delicious farm-to-table meal. Afterward, explore the Sleepy Hollow Cemetery, known for its stunning scenery and famous gravesites. Take a guided tour to learn more about the history and legends of Sleepy Hollow.

Evening

Indulge in a spooky dinner experience at Horseman's Hollow, a haunted attraction that transforms the Philipsburg Manor into a terrifying haunted village. Enjoy a delicious meal while being entertained by actors portraying characters from the legend of Sleepy Hollow.

Bedtime

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Historic Charm and Scenic Views

Morning

Start your day with a leisurely breakfast at The Village Blend, a cozy coffee shop in Sleepy Hollow. Afterward, explore the charming streets of Sleepy Hollow and visit the Sunnyside, the former home of Washington Irving. Take a guided tour to learn about Irving's life and enjoy the beautiful gardens.

Afternoon

For lunch, head to The Twisted Oak in Tarrytown, where you can savor their delicious sandwiches and salads. Afterward, take a scenic hike in the Rockefeller State Park Preserve. Enjoy the peaceful nature trails and stunning views of the Hudson River.

Evening

Enjoy a delightful dinner at The TapHouse in Tarrytown, known for its extensive craft beer selection and mouthwatering burgers. Afterward, take a leisurely stroll along the Tarrytown Waterfront Promenade, enjoying the scenic views of the Hudson River and the Tappan Zee Bridge.

Bedtime

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Art and Culture

Morning

Start your day with a delicious breakfast at The Barn at Sleepy Hollow. Afterward, visit the Kykuit, the historic Rockefeller estate in Pocantico Hills. Explore the magnificent gardens, art galleries, and enjoy panoramic views of the Hudson River.

Afternoon

For lunch, head to The Twisted Oak in Tarrytown, where you can indulge in their mouthwatering wood-fired pizzas. Afterward, visit the Hudson Valley Center for Contemporary Art in Peekskill. Explore the thought-provoking contemporary art exhibitions and immerse yourself in the local art scene.

Evening

Enjoy a sophisticated dinner at The Cookery in Dobbs Ferry, known for its innovative Italian cuisine. Afterward, relax at The Hudson Room, a trendy lounge in Peekskill, where you can enjoy live music and craft cocktails.

Bedtime

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Outdoor Adventures

Morning

Start your day with a delicious breakfast at The Village Blend. Afterward, embark on a thrilling zipline adventure at Go Ape Zipline & Adventure Park in Tarrytown. Soar through the treetops and challenge yourself with various obstacles.

Afternoon

For lunch, head to The Twisted Oak in Tarrytown and enjoy their mouthwatering tacos and refreshing cocktails. Afterward, visit the Rockefeller State Park Preserve again for a leisurely hike or bike ride.

Evening

Treat yourself to a delightful dinner at Red Hat on the River in Irvington, where you can savor their delicious seafood dishes while enjoying scenic views of the Hudson River.

Bedtime

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Culinary Delights

Morning

Start your day with a scrumptious breakfast at The Barn at Sleepy Hollow. Afterward, visit the Tarrytown Farmers Market, where you can explore a variety of local produce, artisanal products, and delicious treats.

Afternoon

For lunch, head to The Twisted Oak in Tarrytown and indulge in their mouthwatering BBQ dishes. Afterward, take a relaxing boat tour along the Hudson River with Classic Harbor Line. Enjoy the breathtaking views and learn about the history of the area.

Evening

Enjoy a memorable farewell dinner at Blue Hill at Stone Barns in Pocantico Hills, known for its farm-to-table cuisine and elegant atmosphere. Savor the seasonal flavors and culinary creations before bidding Sleepy Hollow goodbye.

Bedtime

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