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Spooky and Scenic New England Road Trip Itinerary

Last updated: 2024 Jun 14

Spooky Beginnings in Sleepy Hollow

Morning

Start your day with a pet-friendly breakfast at Sweet Grass Grill, known for its fresh and organic options. Afterward, immerse yourself in the spooky history of Sleepy Hollow with a visit to the Sleepy Hollow Cemetery, the final resting place of Washington Irving and other notable figures.

Afternoon

For lunch, enjoy a meal at Bridge View Tavern with its scenic views of the Hudson River. Afterward, explore the Philipsburg Manor, a historic site that offers a glimpse into the area's past.

Evening

Dine at the atmospheric Horsefeathers, known for its cozy setting and delicious American cuisine. In the evening, take a lantern-lit ghost tour to learn about the legends and hauntings that make Sleepy Hollow famous.

Bedtime

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Literary Charms in Lenox

Morning

Enjoy a leisurely morning with a hearty breakfast at Harvest on Hudson, known for its farm-to-table fare. After breakfast, visit The Mount, Edith Wharton's Home for a glimpse into the life of the famous author.

Afternoon

For lunch, savor the flavors of the region at Xaviars X2O on the Hudson, known for its innovative cuisine. Spend the afternoon exploring the Norman Rockwell Museum to see the iconic works of the beloved American artist.

Evening

Indulge in a fine dining experience at Blue Hill at Stone Barns, known for its sustainable and seasonal menu. After dinner, take a stroll through the quaint town of Lenox and enjoy its charming atmosphere.

Bedtime

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Hiking and History in Woodstock

Morning

Start your day with a delicious breakfast at The Twisted Oak, known for its cozy ambiance. Afterward, embark on a scenic hike in the Mount Tom State Park, which offers stunning views of the surrounding area.

Afternoon

For lunch, enjoy a meal at Red Hat on the River, known for its waterfront dining. Afterward, explore the Billings Farm & Museum to learn about the history of Vermont's rural life.

Evening

Dine at J.P. Doyle's Restaurant and Public House for a taste of traditional Irish cuisine. In the evening, take a ghost tour of Woodstock to uncover the town's eerie legends.

Bedtime

Find amazing hotels in Woodstock, Vermont.