Nestled in the heart of Virginia’s Piedmont region, Orange County offers a captivating blend of history, art, fine dining, and scenic beauty. Whether you’re a history buff, a wine enthusiast, or simply looking for a charming getaway, this 48-hour itinerary will guide you through the best places to stay, eat, and explore.
Day 1: History, Art, and Culinary Delights
Orange County’s rich history and vibrant arts scene provide the perfect foundation for an immersive experience. From exploring presidential history to indulging in local flavors, your first day will be filled with unforgettable moments.
Morning
- Breakfast at Exchange Cafe – Start your day at this cozy café in Barboursville, where breakfast is the star. Exchange Café specializes in hearty breakfast tacos and fluffy biscuits, all crafted with locally sourced ingredients and a touch of Southern charm.
- Visit James Madison’s Montpelier – Dive into history at the former home of the fourth U.S. President. Take a guided tour of the mansion, stroll through the historic gardens, and explore the archaeological sites that reveal the stories of the enslaved community that once lived there.
Afternoon
- Lunch at Forked on Main – Enjoy a farm-to-table dining experience in downtown Orange. The seasonal menu offers locally sourced meats, fresh produce, and an excellent selection of craft cocktails.
- Explore The Arts Center in Orange – Immerse yourself in the local art scene. This gallery showcases the work of regional artists and often hosts workshops and interactive exhibits.
- Stroll through Downtown Orange & Gordonsville Shops – Wander through charming boutiques, antique stores, and artisan shops featuring handmade jewelry, local crafts, and specialty goods.
Evening
- Dinner at Spoon & Spindle – Savor a delightful meal at this cozy yet sophisticated restaurant. Inspired by Southern traditions, the menu includes seasonal specialties and elevated comfort food.
- Overnight at Mayhurst Estate – Unwind at this historic 1859 plantation home turned bed and breakfast. With luxurious rooms, Italian marble fireplaces, and scenic gardens, it’s the perfect place for a relaxing stay.
Day 2: Culture, Wine Tasting, and Scenic Views
Day two offers a perfect mix of cultural enrichment and relaxation. From uncovering historical treasures to sipping fine wines in scenic settings, this day will provide a deep appreciation for the rich heritage and natural beauty of Orange County.
Morning
- Breakfast at Mayhurst Estate – Enjoy a homemade gourmet breakfast, featuring farm-fresh ingredients and local flavors.
- Drive east to the Germanna Foundation Visitor Center – Discover the history of early German settlers in Virginia and explore archaeological sites and exhibits showcasing colonial artifacts.
- Explore the Wilderness Battlefield – Walk the trails and reflect on this key Civil War site, rich in history and natural beauty.
Afternoon
- Lunch at Clear Water Fire-Grill – Refuel with classic American comfort food at this laid-back local favorite. Choose from juicy burgers, smoky BBQ ribs, fresh seafood, and more. Dine in or grab a bite to go before heading to your next destination.
- Return west and stop at Barboursville Vineyards – Spend your afternoon savoring award-winning Virginia wines at one of the region’s most prestigious vineyards. Explore the estate’s scenic grounds, historic ruins, and wine cellar.
- Visit Horton Vineyards – Another must-visit winery, Horton offers a diverse selection of wines, including unique varietals such as Viognier and Norton. Take a tasting flight or enjoy a glass on their scenic patio.
Evening
- Dinner at Well Hung Vineyard – Wrap up your trip with a delicious meal paired with handcrafted wines. The laid-back yet stylish setting makes it a great spot to unwind and reflect on your Orange County adventure.
- Overnight at The Holladay House Inn – Stay in this charming bed and breakfast, one of the oldest structures in downtown Orange. With its historic charm and modern comforts, it’s the perfect place to conclude your weekend getaway.
Experience Orange County and the Legacy of Montpelier
Orange County, VA, offers a perfect blend of history, culture, fine dining, and natural beauty. At the heart of this experience is James Madison’s Montpelier, a site of national significance that provides deep insight into America’s founding and the complexities of its past.
Whether you’re exploring historic sites, sampling local wines, or indulging in gourmet meals, this weekend itinerary ensures a memorable and well-rounded experience. Be sure to visit Montpelier to fully appreciate the rich history that defines this remarkable region.
