Immerse yourself in the history of Charlottesville and Albemarle County, including homes of three Founding Fathers and a colonial era tavern, a wide variety of cuisine and top wineries. Add stops at amazing museums, cultural centers and art exhibitions for a memorable visit.


James Monroe’s Highland

James Monroe’s Highland

Enjoy These Great Charlottesville & Albemarle County Attractions and More:

  • Visit Monticello, Thomas Jefferson’s home
  • Michie Tavern is a historic tavern that dates back to 1784
  • James Monroe’s Highland is the home of the U.S. President and Founding Father
  • Visit 40+ wineries on the Monticello Wine Trail
  • and more


Get More Charlottesville & Albemarle County Travel Info and Subscribe for FREE

Monticello Wine Trail

Monticello Wine Trail

Great Charlottesville & Albemarle County DAY-TO-DAY ITINERARY

DAY 1 of Activities in Charlottesville and Albemarle County

Charlottesville and Albemarle County are home to world-renowned historic sites, including the homes of three of the country’s Founding Fathers. Visit Monticello, Thomas Jefferson’s home, and the University of Virginia, both of which are a single UNESCO World Heritage site. Jefferson was the third president of the United States, author of the Declaration of Independence and the founder of the University of Virginia. Hundreds of thousands of visitors tour Monticello each year and learn about Jefferson’s legacy and complicated history. Monticello offers a variety of guided and self-guided tours for groups.

Michie Tavern is a great spot to enjoy lunch and a tour on your way to or from Thomas Jefferson’s Monticello. Located just half a mile from Monticello, this historic tavern dates to 1784, giving visitors a glimpse into the past and the chance to enjoy an 18th Century, Southern dining experience. Michie Tavern’s popular lunch buffet features southern fried chicken, hickory-smoked pork barbecue, mashed potatoes, black-eyed peas, buttermilk biscuits, cornbread and more. Lunch is served daily from 11:30 a.m. to 3:00 p.m. If you save room for dessert, don’t miss out on the delicious peach cobbler.

Not far from Monticello and Michie Tavern is James Monroe’s Highland, the home of another U.S. President and Founding Father. Highland was purchased by Monroe in 1793 and home to the Monroe family for nearly 25 years. This historical site was acquired by the College of William and Mary (Monroe’s alma mater) in 1974 and today they host events, offer daily tours, and have a great museum shop.

Enjoy dinner at the Dairy Market, a new group food destination located in the historic Monticello Dairy Building. Located in Downtown Charlottesville, not far from the University of Virginia, the space is home to 18 food stalls of varying cuisines, a brewery, restaurant, bar, and several retail shops.

The Looking Glass at IX Art Park.

The Looking Glass at IX Art Park.

DAY 2 More Things To Do in Charlottesville and Albemarle County

Start the day with a walking tour of the historic Grounds of the University of Virginia See and learn more about the Lawn, the Rotunda and UVA’s Memorial to Enslaved Laborers. This memorial honors the 4,000 to 5,000 enslaved people who lived and worked at UVA between 1817 and 1865.

The Jefferson School African American Heritage Center is another important place where visitors can explore a permanent historical exhibit, a rotating contemporary art gallery, and a robust calendar of events. These exhibitions and events highlight Charlottesville and Albemarle County’s African American history and culture of the African diaspora.

The nearby Downtown Mall is a historic, pedestrian mall that is a great spot to enjoy lunch, shop and stroll. Many restaurants offer outdoor dining and groups will be able to choose from a variety of cuisines and price points.

A visit to the Charlottesville area isn’t complete without a stop at one of the 40+ wineries on the Monticello Wine Trail. Experts at one of our regional wine tour companies will plan a customized route suited to your group’s interests and safely transport you from winery to winery. Some companies will even provide a gourmet lunch for your day of vineyard hopping!


If you have time, here are a few more additions to consider adding to your group’s itinerary:

Experience the arts at UVA’s Fralin Museum of Art and the Kluge-Ruhe Aboriginal Art Museum. Kluge-Ruhe is the only museum outside of Australia dedicated to the exhibition and study of Indigenous Australian art. The permanent collection of The Fralin Museum of Art consists of nearly 14,000 objects. The IX Art Park offers another unique art experience at The Looking Glass, Virginia’s first immersive art exhibition. Finally, if your group is headed North, you won’t want to miss Montpelier, the home of U.S. President and Founding Father James Madison. Enjoy Montpelier’s grounds, explore the museum shop, and take a guided tour.

The Charlottesville area was recently named Wine Enthusiast’s Wine Region of the Year and features 40+ wineries on the Monticello Wine Trail.

Request More Travel Information for FREE