Episode 9 Itinerary: Explore Lesser-Known History (Craft and Creativity)
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Episode 10 Itinerary: Explore Lesser-Known History (Monticello and Charlottesville)
In the tenth and final episode of Founding Footprints: Tracing America’s Journey in Charlottesville & Albemarle County, historian Benjamin Bernard heads to Monticello, Thomas Jefferson’s beloved mountaintop home. There, he chats with Jane Kamensky, President and CEO of the Thomas Jefferson Foundation. Monticello is a house museum and so much more. Through many avenues, such as collections, architectural restoration, archaeology, environmental stewardship, gardens, scholarship, oral history, educational programs, and tours, Monticello staff members preserve, protect, grow, research, and interpret the legacy of Thomas Jefferson, his family and friends, and all who lived and labored at the plantation, including the hundreds of people who were enslaved, many of whom were leaders in their own right.
We’ve put together an itinerary that helps you explore this iconic place and how it continues to play a role in history, civics, and community for the nation and Charlottesville and Albemarle County.
Listen to the Founding Footprints podcast HERE or on your favorite audio streaming platform.
Itinerary Length: 2.5 – 3 days
Day 1: Spend the Day at Monticello
As the primary author of the Declaration of Independence (1776), its precursor A Summary View of the Rights of British America (1774), and the Virginia Statute for Religious Freedom (drafted in 1779 and passed into law in 1786), Thomas Jefferson gave voice to ideals that cultivated democracy through the centuries and around the world. However, his lifestyle reflects a different reality. Monticello connects us with this duality, which was inherent to Jefferson and the founding of the United States.
1. Stamp Your Passport
Be sure to request a stamp for your Virginia 250 Passport. Don’t have a passport yet? Monticello is one of five signature sites where you can pick up one to start exploring history organizations around the Commonwealth, earn discounts on admission, and be eligible for prizes.
2. Tour the Mansion and Grounds
Experience Monticello through a Highlights Tour or Founding Friends, Founding Foes Tour. Your ticket also allows you to join two guided walking tours: one that directs you around the extensive gardens and one focused on slavery at Monticello.
3. Dine On-Site with a Feast of Reason Experience
Eat lunch at the Monticello Café where the casual menu of sandwiches, salads, and bowls incorporates local ingredients. Or take your order “to go” to gather with other visitors for a Feast of Reason experience. Offered every Thursday – Sunday at 1:30 pm in the Woodland Pavilion, Feast of Reason uses guided questions to encourage Jeffersonian-style mealtime conversations about history and civic life. Geared to guests 12 years and older and available until October 25.
4. Examine Artifacts and Personal Stories
Explore newly curated exhibition galleries at Monticello’s David M. Rubenstein Visitor Center. Reopened in spring 2026 in honor of the nation’s semi-quincentennial, galleries are free to visit and do not require a ticket or reservation.
Insider Tip: Families can investigate the past with hands-on activities at the revamped Griffin Discovery Room. Great for kids ages 5 – 10 years old!
5. Hit the Trail
Walk or bike the popular Saunders-Monticello Trail, which winds its way through native hardwood forest and meadow along the mountainside from Monticello’s Visitor Center to Route 20. The main trail totals four miles roundtrip, and a maximum grade of 5% keeps it accessible. Looking for a challenge? Add a hike of the Mountain, Eagle Scout, or Jason Stevens Trail.
6. Shop for the 250th
Find gifts – both meaningful and fun – at the Shop at Monticello.
7. Hear from Jefferson Himself
Join Bill Barker as he interprets Thomas Jefferson during his retirement years. Jefferson Remembers the Declaration is offered every Wednesday – Saturday afternoon between now and July 31.
8. Wine Down Your Afternoon
Sip wine at Jefferson Vineyards, situated on land where Jefferson’s friend Philip Mazzei first started growing vitis vinifera grapes in 1774, or Eastwood Farm and Winery, once home to Jefferson’s master builder John Dunkum. Both wineries are part of the Monticello AVA, considered the birthplace of American wine. Their wines speak to this history, the terroir of the Virginia Piedmont, and a willingness to experiment and collaborate. You can learn more about the community of local winemakers in Founding Footprints Itinerary 7.
Day 2: Explore Jefferson’s Hobbies
Thomas Jefferson’s interests ranged from architecture, astronomy, and botany to meteorology and travel. He was an avid reader and writer; collector of books, maps, fossils, plants, and seeds; aficionado of wine; enthusiastic gardener, and skilled amateur musician. Today, he would be considered a foodie, citizen scientist, and proponent of life hacks! It is these hobbies that gave direction to his daily life and transformed Monticello and the University of Virginia into functional laboratories to test his ideas. These hobbies also built and deepened friendships and generational family ties. Devote Day 2 to exploring just a few of Jefferson’s hobbies in Charlottesville and Albemarle County. Perhaps you share a common interest.
1. Breakfast with Creativity and Culture
In 1815, Jefferson famously wrote to John Adams, "I cannot live without books; but fewer will suffice where amusement, and not use, is the only future object." Jefferson amassed three major collections of books during his lifetime. The second and largest, totaling about 6,500 books, was sold to the federal government in 1814 to form the core of the Library of Congress.
2. Discover the Downtown Book District
Search independent bookstores on Charlottesville’s Downtown Mall, like 2nd Act Books, Blue Whale Books, Daedalus Bookshop, Hello Comics Downtown, New Dominion Bookshop, and The Beautiful Idea, for your next favorite read or literary keepsake. Commerce Street Books in nearby Midtown and Gingko Bookshop on the UVA Corner are worth a short detour.
3. *Bonus: Plan to Attend the Virginia Festival of the Book*
Held each March, the Festival of the Book brings nationally known authors to the area. It’s a perfect getaway for those who love to read about history, folklife, and folklore, as well as historical fiction and family narratives. Author talks, many of which are free to attend, are held at locations around Downtown and UVA as well as at Monticello and James Monroe’s Highland.
Insider Tip: Gift shops at both presidential homes have extensive selections of history books for sale!
4. Lunch at Hamiltons’ at First and Main
Despite sharing a name with Jefferson’s fiercest political rival, Hamiltons’ at First Main takes greater inspiration from Jefferson’s hospitality style. The menu combines French technique with seasonality of ingredients and culinary traditions from Virginia and around the world. Order the daily Vegetarian Blue Plate Special to emulate vegetable lover Thomas Jefferson!
"but though an old man, I am but a young gardener."
Thomas Jefferson wrote to artist and fellow gardener Charles Wilson Peale during the summer of 1811. The letter captures Jefferson’s lifelong passion for gardening and innovative agriculture and his belief that there is always something new to learn.
5. Shop Local Garden Centers
Look for plants and gardening solutions at both locations of Blue Ridge Farmers Co-Op, Eltzroth & Thompson, Fifth Season Gardening, Ivy Creek Garden Center, Ivy Nursery, and Snow’s Garden Center.
6.*Bonus: Attend Annual Garden Events*
Mark your calendar for upcoming events at the Thomas Jefferson Center for Historic Plants (CHP). A department of Monticello and located at nearby Tufton Farm, the CHP hosts Open House Plant Sales four times a year – twice in spring and twice in autumn. It is also home to collections of heirloom roses and irises as well as the growing nursery for plants sold at Monticello’s shop and online catalog.
Don’t miss Historic Garden Week! Considered the only statewide house and garden tour in the nation, Historic Garden Week is held throughout Virginia in late April, including three days of tours specifically geared to garden lovers in Charlottesville and Albemarle County. It is easy to plan an extended itinerary with visits to art galleries, working farms, and other historic sites, including Monticello and James Madison’s Montpelier – two restoration projects supported by the annual event. Watch for updates to our Garden Week guide to start making plans.
7. Eat Ice Cream
Indulge in homemade sweets at local ice cream “parlors” like Chaps Downtown and on the UVA Corner, Crozet Creamery, La Flor Michoacana, Splendora’s, and SugarBear near the Rivanna River and on Ivy Road. Carter Mountain Orchard and Chiles Peach Orchard are go-to destinations for soft-serve. Jefferson was a fan of ice cream and brought back a recipe after living in France, so the creamy dessert could be served at Monticello.
8. Listen to Live Music
Take in a performance at The Jefferson, Paramount Theater, Southern Café and Music Hall, or Ting Pavilion, all of which attract nationally known artists and foster regional talent. Live music sessions at local wineries like Albemarle CiderWorks, Chisholm Vineyards at Adventure Farm, and Keswick Vineyards allow you to sample Charlottesville’s roster of singer songwriters and folk and jazz musicians.
Insider Tip: Performance groups like the Early Music Access Project, Three Notch’d Road: The Virginia Baroque Ensemble, and Zephyrus introduce you to music that would have been known in colonial times and the early years of the United States. Concerts by the volunteer Cville Band, founded over a century ago, are always free to attend and remind us that music is often a form of civic engagement!
Thomas Jefferson courted his wife Martha Wayles Skelton with music. Playing instruments like the violin, guitar, harpsichord, and piano was a favorite pastime of their daughters and grandchildren. Beverly, Eston, and Madison, the three sons of Sally Hemings and Thomas Jefferson, as well as their cousins from the Scott family, were well-known and accomplished fiddlers whose contributions to musical traditions during our nation’s founding are being re-discovered today.
Day 3: Yes, Monticello is Charlottesville
Many visitors have heard of Monticello but not Charlottesville. Conversely, some have visited Charlottesville without realizing Monticello is just minutes away. Visualizing Albemarle County, which encompasses over 720 square miles and whose founding predates both Charlottesville and Monticello, can be difficult…even for residents.
Monticello, Charlottesville, and Albemarle County are intrinsically linked through Thomas Jefferson, his ideas, his family and friends, and so many other people – enslaved and free – who lived or worked at the estate. In Day 3, we recommend you explore these connections between the mountaintop and life in Charlottesville and Albemarle County.
1. Start Your Day with Coffee
2. Take a Tour
Sign up for a guided walking tour with the Albemarle Charlottesville Historical Society. Learn more about the history of Court Square or the Downtown Mall. Hear stories about the individuals and families who helped to shape community and commerce here.
Be sure to stop at the First Amendment Monument, often known as the Community Chalk Wall. Located at the east end of the Downtown Mall near City Hall and the Ting Pavilion, the wall encourages the continued practice of free expression.
3. Go to the Jefferson School
View the history and contemporary art exhibits at the Jefferson School African American Heritage Center – open Tuesday - Saturday. Founded as a primary and normal school during Reconstruction, the Jefferson School we see today opened in 1926 as Charlottesville’s first high school for Black students during Jim Crow segregation. It was expanded in the 1930s and 50s. Use the JSAAHC app to explore Black culture both within this landmark building and surrounding neighborhoods. Read Founding Footprints Itinerary 5 to learn more about public education and civil rights in Charlottesville and Albemarle County.
4. Walk Around the University of Virginia
Predominantly built between 1817 and 1828, the original buildings at the University of Virginia were designed by Thomas Jefferson and constructed by many of the craftspeople – free and enslaved – who had worked at Monticello. Jefferson called the configuration of space and structures his Academical Village, and it includes the Rotunda, ten Pavilions, divided by student rooms, surrounding a terraced Lawn. There are also gardens and outer “Ranges” of working buildings and more student rooms. Classes were first held at UVA in 1825. Jefferson was involved in every aspect of founding the school, and his friends James Madison and James Monroe served on its inaugural Board of Visitors. Today, the Academical Village is part of the UNESCO World Heritage Site designation, along with Monticello. It is the focal point of UVA’s Central Grounds and vital to both daily life and special celebrations at the University.
Go inside the Rotunda, the centerpiece of Jefferson’s design. It is open most days, 9AM until 5PM, free of charge. Visitors can explore all three floors and should enter the Rotunda on the Lawn side. The Lower East Oval Room houses an exhibit of historical artifacts and an early 18th century chemical hearth that are must-sees. Don’t miss the Dome Room on the third floor. Explore the Pavilion gardens and stop by Edgar Allan Poe’s room at 13 West Range. UVA Obscura is a helpful tool to find hidden history!
Take advantage of free tours led by the Virginia Guide Service during the academic year. Standard hour-long history tours leave from the Rotunda steps, at 11AM, Friday-Sunday, when regular UVA classes are in session.
5. Visit the Memorial to Enslaved Laborers
6. See the Declaration of Independence
UVA is also home to the Albert and Shirley Small Special Collections Library, which contains one of the largest and most comprehensive collections devoted to the Declaration of Independence. The permanent exhibit “Declaring Independence” is free to visit and allows visitors an up-close look at John Dunlap’s broadside – the officially sanctioned document of the Second Continental Congress – printed July 4 – 5, 1776.
Insider Tip: When making plans, double check hours of operations at UVA as they may be scaled back during summer months and over the winter holidays.
7. Stop at James Monroe’s Highland
Discover Highland, the local home of James Monroe, Revolutionary War veteran, 5th president of the United States, and friend and mentee of Jefferson. General admission to Highland includes entry to interior exhibits in the 1818 Guesthouse, the A Window to a New America exhibition, developed in collaboration with Highland’s Council of Descendant Advisors, and exploration of outdoor spaces. You can also collect a stamp for your Virginia 250 Passport.
8. Celebrate Mac and Cheese
A staple of American cuisine and home cooking today, macaroni and cheese would have been a novelty in the late 18th and early 19th centuries. James Hemings accompanied Jefferson to Europe as an enslaved servant and trained as a chef in some of the top establishments and homes of pre-Revolutionary France. He returned to the United States with a cadre of recipes and cooking techniques, such as cheesy baked pasta, but still enslaved. Hemings led the kitchens at Jefferson’s residences in New York and Philadelphia, and later worked in Baltimore, thereby influencing dining in these sophisticated urban centers. James Hemings also passed along his knowledge to his brother Peter Hemings at Monticello.
Honor this cultural and familial exchange by dining at Black Cow Chophouse, Fardowners Restaurant, The Jervey, Maya, or The Virginian where mac and cheese is a specialty of the menus.
Virginia is for History Lovers. Listen to all 10 episodes of Founding Footprints and make your travel plans now. Charlottesville and Albemarle County offer a variety of places to stay including resorts, inns, B&Bs, hotels, and vacation rentals – so you can book the lodging that aligns with your travel preferences.