The Monticello Wine Trail is the heart of Virginia wine country, a region shaped by Thomas Jefferson’s early ambition to create an American wine legacy. Today, more than 40 wineries sit within 25 miles of Charlottesville, offering visitors a chance to enjoy award-winning vintages, gorgeous scenery, and inviting tasting rooms. With its national and international acclaim, plus the 2023 Wine Region of the Year recognition from Wine Enthusiast, the Monticello Trail is one of the most exciting things to do in Charlottesville, VA.
This well-known trail originated from Thomas Jefferson’s initial plantings at Monticello and nearby farms, where he and Filippo Mazzei aimed to cultivate vineyards that could rival those in Europe. Their efforts faced numerous setbacks due to war, prohibition, and lengthy recovery periods during the Great Depression and World War II. However, progress gained momentum in 1976 with the establishment of Barboursville Vineyards. Since then, the region has continued to evolve, with dedicated winemakers pursuing the dream that Jefferson never had the chance to fulfill.
As you explore these wineries, a stay at The Orchard House B&B offers a relaxing base for your getaway. You can enjoy warm hospitality, comfortable spaces, and an ideal location close to the best Charlottesville wineries. Whether you are planning a romantic escape or a fun wine-focused visit with friends, our charming Bed and Breakfast near Charlottesville is the perfect starting point for every outing. We can’t wait to host you; book your stay today!
Discover the Monticello Wine Trail in Virginia's Wine Country
The Monticello Wine Trail is one of the top things to do in Charlottesville, VA, bringing visitors from across the country to enjoy scenic drives, tasting rooms, and vineyard views. With more than 40 wineries located within 25 miles of Charlottesville, the Monticello Wine Trail offers history, culture, and modern winemaking. There is a wide variety of tasting experiences from small family-run vineyards to large estates with celebrated restaurants. With so many options, it’s easy to see why this region is considered the birthplace of American wine and a must-visit highlight of Virginia wine country.
Many travelers combine their tasting with dedicated transportation to explore the Monticello Trail at a relaxed pace, for safety and convenience. These services allow you to enjoy every tasting without worrying about driving between vineyards. They also offer local insight, winery recommendations, and route planning, making it even easier to experience the best of the Monticello Wine Trail and the surrounding Virginia wine country.
Wineries to Visit on the Monticello Wine Trail within one hour of our B&B
- Blenheim Vineyards, founded by Dave Matthews in 2000, features reclaimed wood architecture and a cellar visible through glass flooring. They serve excellent Chardonnay, Viognier, Cabernet Franc, Petit Verdot, and Cabernet Sauvignon.
- Jefferson Vineyards, located between the Monticello and Highland estates, is rich in historical significance, boasts a strong Wine Spectator track record, offers indoor seating by the fireplace, and produces highly-rated Viognier.
- Early Mountain Vineyards, known for its Virginia Table menu, has one of the most beautiful tasting rooms on the Monticello Trail. The vineyards sit on a 350-acre setting, and award-winning wines are crafted by Winemaker Maya Hood White.
- Keswick Vineyards is one of the best Charlottesville wineries. This family-owned estate located on the scenic Route 231 has earned major awards, including multiple Governor’s Cups. They are open daily with live music on Wednesdays.
- Barboursville Vineyards invites visitors to explore a celebrated estate featuring landmark ruins of the home designed for Governor James Barbour by Thomas Jefferson. Guests can enjoy tastings in the Octagon Barrel room featuring Italian-influenced varietals such as Nebbiolo.
Safe Designated Driver Wine Tours for the Monticello Wine Trail
- Albemarle Limousine offers polished service for wine tours in Virginia. Guests enjoy professional drivers, comfortable vehicles, and custom schedules that make it easy to visit several Monticello Trail wineries in one day.
- Blue Ridge Drivers, offering four or five-hour minimum tours, depending on the day of the week, giving you plenty of time to enjoy multiple wineries on the trail. You can choose the wineries yourself, or let your driver build a route based on your preferences. Their knowledge of the Monticello Wine Trail makes them a helpful resource for travelers who love flexibility.
- Norm’s Executive Transportation offers black-car service with comfortable interiors and experienced drivers. This company focuses on a smooth and luxurious ride, making it a popular choice for couples, small groups, and special celebrations.
- A TripAdvisor Travelers’ Choice Award winner for 2025, Monticello Wine Tour and Coach Co. is one of the most trusted transportation companies for Monticello Wine Trail visitors. The team handles custom itinerary design, winery reservations, timing, and transportation details, letting you sit back and enjoy your day in Virginia wine country.
Stay at Our Bed and Breakfast near Charlottesville
After a full day exploring wineries and savoring the best of the Monticello Trail, return to our inviting Bed and Breakfast near Charlottesville to unwind. Our property offers a peaceful setting close to everything you want to see, with porches, outdoor seating, and common indoor spaces that help you relax between tastings. Guests appreciate the ideal location, as it makes visiting the best Charlottesville wineries, vineyards, and other best things to do in Charlottesville simple and enjoyable.
Breakfast is a highlight of your stay at our Bed and Breakfast near Charlottesville, featuring fresh ingredients, thoughtful menus, and friendly service each morning. We truly enjoy cooking for you! These meals help you ease into the day before heading out for more wine tours in Virginia or an afternoon of sightseeing. Many guests say breakfast becomes one of their favorite moments, thanks to the leisurely pace and delicious offerings.
The guest rooms at our Bed and Breakfast near Charlottesville offer a warm, comfortable retreat with charming decor and modern conveniences. Each room is designed to ensure your stay feels relaxed, whether you are here for a romantic getaway or a weekend exploring Virginia wine country. With inviting beds, private bathrooms, and thoughtful amenities, your stay is the perfect complement to your Monticello Wine Trail adventure. Reserve your room today!