Charlottesville and Albemarle County, located in central Virginia, are home to worldrenowned historic sites, a variety of culinary options, and world-class wineries, making the area the perfect place to visit for the 250th anniversary of the nation in 2026. The region offers an immersive experience where visitors can explore the country’s early history, learn about the legacies of the country’s former presidents, and appreciate the complex and multifaceted stories that shaped the nation. Whether you’re a history enthusiast, a wine lover, or someone who enjoys beautiful landscapes and fine dining, your group won’t want to miss the Charlottesville area.

One of the major highlights of the region is Monticello, the home of Thomas Jefferson, third president of the United States, author of the Declaration of Independence, and founder of the University of Virginia. Alongside the Rotunda at the University of Virginia, Monticello is a UNESCO World Heritage site and attracts hundreds of thousands of visitors annually. Visitors to Monticello can tour the house, see the gardens, and learn about Jefferson’s innovations in architecture and agriculture. They can also take part in various educational programs that address Jefferson’s role in shaping America and the complex history of slavery in early America. The breathtaking views from the mountaintop estate are also not to be missed, as they give a unique perspective on the landscape that Jefferson cherished.

After touring Monticello, a perfect lunch stop is Michie Tavern, located just half a mile from Jefferson’s home. This historic tavern dates back to 1784 and offers a chance to experience an 18th-century Southern dining experience. The tavern serves a buffet of traditional Southern fare, including southern fried chicken, hickory-smoked pork barbecue, mashed potatoes, black-eyed peas, buttermilk biscuits, cornbread, and more. The buffet is served daily from 11:30 a.m. to 3:00 p.m., and visitors can also take a guided tour of the tavern, which highlights its role as a resting place for travelers in the 18th century. Don’t forget to indulge in the homemade peach cobbler for dessert—it’s a local favorite!

Not far from Monticello and Michie Tavern is James Monroe’s Highland, the home of the fifth U.S. president. Purchased by Monroe in 1793, this historic estate was home to the Monroe family for nearly 25 years. The property was acquired by the College of William and Mary, Monroe’s alma mater, in 1974, and today, it offers daily tours and hosts a variety of educational events. For those who wish to continue their exploration of presidential homes, James Madison’s Montpelier is a short drive away.

In the evening, consider heading to the Dairy Market for dinner. Located in the historic Monticello Dairy Building in Downtown Charlottesville, this group food destination features more than a dozen merchant stalls offering a variety of cuisines, from classics like burgers to international fare. The space also includes a brewery, retail shops, and an exciting new addition—a duckpin bowling alley, set to open in the spring of 2025. Whether you’re looking for a casual meal or a fun group activity, the Dairy Market is a
great place to relax after a busy day of sightseeing and enjoy the company of friends or fellow travelers.

On the second day of your visit, start with a walking tour of the historic Grounds of the University of Virginia. Founded by Thomas Jefferson in 1819, the University is known for its central feature, the Rotunda and the Lawn. Also on the grounds is the Memorial to Enslaved Laborers, which honors the 4,000 to 5,000 enslaved individuals who lived and worked at the University between 1817 and 1865. This memorial offers a sobering and
thoughtful reminder of the complexities of American history and the contributions of enslaved people to the institution’s success.

To continue exploring the area’s Black history, a must-visit during your time in Charlottesville is the Jefferson School African American Heritage Center. Located within the Jefferson School City Center, which celebrates its 100th anniversary in 2026, this cultural institution offers a wealth of information about the history and culture of African Americans in Charlottesville and Albemarle County. The center features permanent art exhibits, rotating contemporary galleries, and a vibrant calendar of events. It serves as an important resource for understanding the African American experience in the region and highlights the legacy of African Americans in the area. The exhibitions focus on the rich cultural heritage and artistic contributions of the African diaspora, offering visitors a deeper understanding of Charlottesville’s history.

Next up, head to the nearby Downtown Mall for lunch and a leisurely stroll. The Downtown Mall, which celebrates its 50th anniversary in 2026, is a historic pedestrian mall lined with shops, cafes, and restaurants. It’s the perfect place to relax, people watch, and sample local cuisine. Many restaurants offer outdoor seating, making it an ideal spot to enjoy a meal while soaking in the vibrant atmosphere of downtown Charlottesville.

The Charlottesville area is also known for its wine, and no visit would be complete without exploring the Monticello Wine Trail. Recently named Wine Enthusiast’s Wine Region of the Year, the trail features nearly 50 wineries set against the stunning backdrop of the Blue Ridge Mountains. Whether you’re a wine connoisseur or just enjoy the occasional glass of wine, the Monticello Wine Trail offers a wide variety of experiences. Local wine tour companies can customize your group’s itinerary, ensuring a safe and scenic journey through the region’s best vineyards. Wine lovers will
appreciate the opportunity to sample award-winning wines while enjoying the beauty of the Virginia countryside. Charlottesville and Albemarle County offer a unique combination of history, culture, and natural beauty that makes it an unforgettable destination. Whether you’re interested in exploring the foundations of American democracy, enjoying world-class cuisine, or exploring the vibrant wine scene, the Charlottesville area is a place that will leave a lasting impression. As the nation celebrates its 250th anniversary in 2026, there is no better time to visit and experience this historic region.

Learn more about group travel in Charlottesville and Albemarle County at
visitcharlottesville.org/groups.