5-day Trip to Winchester, Virginia Itinerary

Start your day with a hearty breakfast at The Butcher Station and fuel up for an adventurous day ahead. Head to Shenandoah Valley Discovery Museum to explore interactive exhibits and learn about the region's natural and cultural heritage.

For a delicious lunch, visit The Hideaway Cafe and enjoy their mouthwatering sandwiches. Afterward, embark on a scenic hike at Shenandoah National Park and immerse yourself in the breathtaking beauty of nature.

Treat yourself to a delightful dinner at Village Square Restaurant and savor their delectable seafood dishes. End the day with a relaxing drink at Brewbaker's Restaurant, a local brewery known for its craft beers.

Start your day with a delicious breakfast at George's Food & Spirits. Afterward, head to Veramar Vineyard for a scenic wine tasting experience in the beautiful countryside.

Enjoy a delightful lunch at Roma Old Town Wood-Fired Pizzeria and savor their authentic Italian pizzas. Afterward, visit Cedar Creek and Belle Grove National Historical Park to learn about the history of the Civil War and explore the picturesque grounds.

Indulge in a gourmet dinner at L'Auberge Provencale Bed & Breakfast and savor their exquisite French cuisine. Afterward, relax with a glass of wine at Sweet Caroline's and enjoy the cozy ambiance.

Start your day with a scenic drive to Harpers Ferry, West Virginia. Enjoy a delicious breakfast at The Anvil Restaurant before exploring the historic town. Visit Harpers Ferry National Historical Park to learn about its role in the Civil War and enjoy stunning views of the Shenandoah and Potomac rivers.

For lunch, try The Country Cafe and savor their homestyle dishes. Afterward, embark on a hike along the Appalachian Trail and immerse yourself in the beauty of nature.

Enjoy a delightful dinner at The Barn of Harpers Ferry and savor their farm-to-table cuisine. Afterward, explore the charming shops and art galleries in Harpers Ferry before heading back to Winchester.

Start your day with a scenic drive to Charlottesville, Virginia. Enjoy a delicious breakfast at MarieBette Cafe & Bakery before exploring the city. Visit Thomas Jefferson's Monticello to learn about the life of the third U.S. President and admire the stunning architecture.

For lunch, try The Local and savor their farm-to-table dishes. Afterward, visit University of Virginia and take a stroll through its beautiful campus.

Indulge in a gourmet dinner at The Alley Light and savor their exquisite French-inspired cuisine. Afterward, enjoy a relaxing drink at Commonwealth Restaurant & Skybar and take in the panoramic views of Charlottesville.