Monticello and Charlottesville, Virginia: A Walk in Jefferson’s Footsteps

Thomas Jefferson's Monticello in Charlottesville, Virginia

Virginia and US history often go hand in hand. Eight of America’s presidents were born in the state, as were eight of the people who signed the Declaration of Independence. The first English settlement was founded in Jamestown, and the final surrenders of two major wars fought on United States soil occurred in Virginia—the Revolutionary War, which ended in Yorktown, and the American Civil War, which ended at Appomattox. In a state brimming with historical places, one of our favorite cities to visit is Charlottesville.

Jefferson statue at UVA
Jefferson statue at UVA
Charlottesville, and Thomas Jefferson’s Monticello specifically, holds a special place in our hearts: Adam and I visited on one of our first dates and, years later, got engaged there. Adam is also a proud alumnus of University of Virginia (UVA), and we’ve spent many weekends driving south on scenic Route 29 as we’ve trekked to UVA football games, wineries, restaurants, and historic house tours. Charlottesville is both a youthful college town and a family-oriented community without losing its deep roots in Virginia’s history, which to us is best explored through the eyes of Thomas Jefferson. Jefferson, the third American president, left an indelible mark on the town. Charlottesville is about an hour from Richmond, 2.5 hours from Washington, DC, and 4.5 hours from Philadelphia, which makes it a great destination for a day trip or a weekend trip if you are based in or passing through the Mid-Atlantic states.

If a day spent learning, exploring, and relaxing sounds like a great day trip to you, here is how we use a walk in Jefferson’s footsteps to introduce friends and family to Charlottesville, Virginia.


“I am as happy nowhere else & in no other society, & all my wishes end, where I hope my days will end, at Monticello. Too many scenes of happiness mingle themselves with all the recollections of my native woods & fields, to suffer them to be supplanted in my affection by any other.”

– Thomas Jefferson

The fish pond at Monticello
The fish pond at Monticello
Charlottesville’s crown jewel is the beautiful UNESCO World Heritage Site Monticello, the home Jefferson designed and where he lived, entertained guests, and ultimately passed away on July 4, 1826. Jefferson inherited the property when he was just 26 years old, and he spent decades building and remodeling portions of the house based on trends and styles he discovered during trips to Europe. Monticello was often a bustling hub for Jefferson’s extended family (including his daughter Martha and her children, who lived there) and numerous guests including President James Madison and his wife Dolley. Jefferson despised wasted space, which resulted in a home with a unique layout and some charming features.

A visit to Monticello should always include a house tour. We have taken dozens of house tours as we have accompanied guests to Charlottesville over the years, and the tours are unwaveringly informative and interesting. Starting with a quick shuttle drive that whisks visitors to the mountaintop where the house is located, tours begin with an introduction to Jefferson’s life and importance in the front hall. The room is full of fascinating finds, including the upper jawbone of the now extinct mastodon and elk antlers sent back by Lewis and Clark (whose famous expedition was commissioned by Jefferson in 1803). Above the doorway hangs one of my favorite components of the house, the Great Clock that uses cannonball-like weights to both keep time and identify the day of the week (although when the clock was installed the cannonballs required more room than was available, which meant a hole was cut into the floor and the weights disappear from view on Saturdays). A walk further into the house unveils my favorite room, Jefferson’s library. Jefferson famously told President John Adams in a letter, “I cannot live without books,” and he owned more than 6,500 books during his lifetime. When British forces burned the US Capitol Building during the War of 1812, Jefferson sold the vast majority of his personal collection to his country, and those books became the foundation of our Library of Congress.

Cameras are not allowed inside Monticello, but you are allowed to use them outside the building. The video below highlights some of the interesting items and locations inside the building as selected by Monticello guides and staff.


Jefferson and Monticello on the US Nickel
Jefferson and Monticello on the US Nickel
While an indoor house tour will take approximately 45 minutes, Monticello offers two additional tours that are included with an admission ticket. On a nice day, the Gardens and Grounds tour takes an in-depth look at Jefferson’s love of gardening and horticulture. Monticello sits on a beautifully landscaped property, and even independent visitors will love exploring the flower walk, the fish pond, and the grove that surround the west lawn. From the edge of the west lawn, you will also see the same image of Monticello that is represented on the back of the nickel, the coin on which Jefferson’s image also appears.

Slavery remains a critical conversation for visitors to Monticello, and the 45-minute Slavery at Monticello tour provides an honest look at the role slaves played at Jefferson’s estate. Jefferson publicly spoke against slavery and specifically wrote that, “All men are created equal” in the Declaration of Independence. Still, more than 600 men, women, and children were enslaved at Monticello during his life. His views were complicated—and not always correct—and Monticello’s educational programming advances the conversation by presenting what is currently known about slavery at Monticello. Additionally, a new exhibit shares insights into Jefferson’s relationship with Sally Hemings; DNA evidence has confirmed Jefferson fathered at least six of her children. The tour is an important component of a visit to Monticello.

There is also a wonderful annual event held at Monticello every year on the 4th of July: a naturalization ceremony for new American citizens. Thomas Jefferson famously opened up the White House (called the President’s House at that time in history) to the public every year on July 4th, so it is in this same tradition that Monticello offers free access to both the naturalization ceremony and the house itself. We attended in 2013 when Dave Matthews—the founder of the Dave Matthews Band—delivered the keynote address to welcome the new Americans. His words about what being a citizen mean to him as a longtime Charlottesville resident paid an incredible tribute to the country and to Monticello.

Dave Matthews speaking at Monticello's naturalization ceremony
Dave Matthews at Monticello’s naturalization ceremony (Video)
Plan to dedicate a few hours of your day in Charlottesville to Monticello. In addition to the house tour, optional guided tours, and independent exploration time, there is also a beautiful visitors center and a café that are worth a visit before or after your house tour. We recommend arriving early (30-60 minutes before your tour) to walk through the visitor’s center before taking the shuttle to the mountaintop. If the weather is nice and you feel like a walk, skip the shuttle ride on the way back and walk down the trail instead. You’ll have the chance to stop at Jefferson’s gravesite, where his gravestone proudly notes he is the author of the Declaration of American Independence and of the Statute of Virginia for religious freedom and the Father of the University of Virginia. Notably, his service as President of the United States is not mentioned. Why would such a position of relevance and importance be omitted? In his instructions, he stated, “On the faces of the Obelisk the following inscription, & not a word more… because by these, as testimonials that I have lived, I wish most to be remembered.” The shuttle will stop at Jefferson’s final resting place, so if walking isn’t preferable you can still have a chance to see it.

Spending a half day or longer is easy to do at Monticello. When planning your day trip to Charlottesville, plan to give yourself as much time as possible—you’ll see a lot and learn even more!

More Information:

The University of Virginia

“This institution will be based on the illimitable freedom of the human mind. For here we are not afraid to follow truth wherever it may lead, nor to tolerate any error so long as reason is left free to combat it.”

– Thomas Jefferson

The Rotunda at UVA
The Rotunda at UVA
Standing just a few hundred feet from Monticello on the North Pavilion, visitors can clearly see a lone white dome just five miles away. The dome belongs to the University of Virginia’s Rotunda, a project Jefferson proudly and passionately guided in his later years. Jefferson was a graduate of Virginia’s first university—the College of William and Mary—but was unhappy with its religious ties that Jefferson believed stifled education. He deeply desired a university that would offer a strong education without religious overtones, and along with Presidents James Madison and James Monroe he selected the location for the university, which was chartered by the state in 1819. He designed UVA’s grounds and what he referred to as the “Academical Village,” the central portion of the university. He also designed architectural elements like the Serpentine Walls, which look like waves and are only a single brick in thickness.

The Academical Village is most recognized by the Rotunda, which was inspired by the Pantheon in Rome. Because UVA did not have a church as its focal point, the Rotunda became the symbol of Jefferson’s belief in the distinct separation of church and education. Extending beyond the Rotunda and down the Lawn are a series of rooms that today house fourth year students, who are selected to live there by application. The rooms are part of UVA’s rich legacy of community, but they have their drawbacks: rooms do not have their own bathrooms, air conditioning, or kitchens.

Edgar Allan Poe's room at UVA
Edgar Allan Poe’s room at UVA
Graduate students are afforded a similar housing opportunity at the Range, a series of rooms not far from the Lawn. One of the most famous students and Range residents was Edgar Allan Poe, who lived there for 10 months in 1826. Poe was known as a good student who entertained friends in his room with readings, but his adoptive father was unable to pay his tuition and Poe left UVA when he gambled his way into personal debt and was also unable to afford an additional semester. Today, visitors to UVA can see Poe’s room (appropriately room #13), which is maintained by the University’s Raven Society.

Like Monticello, University of Virginia has the UNESCO World Heritage Site designation and is worth visiting when you are in Charlottesville. A walk through campus can take as little as 30 minutes or as long as an hour or two depending on your speed and what catches your eye. During the autumn months, Saturdays can mean football games- while that can equate to larger crowds and more traffic, for us it means a chance to enjoy some of UVA’s spirit and experience the campus when it is most alive.

More Information:

Barboursville Winery

The Barboursville Ruins
The Barboursville Ruins
We love Virginia wineries, and just 40 minutes northeast of Charlottesville one great winery has a unique tie to Charlottesville and Thomas Jefferson. Barboursville Winery was owned by James Barbour, a former governor of Virginia and personal friend to Jefferson. Jefferson designed a home for the Barbour family that was built on the property, which included an octagonal drawing room not unlike the octagonal rooms he incorporated into his homes at Monticello and Poplar Forest, a summer home. However, in 1884 a fire on Christmas day destroyed the house. The house was not rebuilt, but the ruins remain and are owned by the winery. For another chance to see Jeffersonian architecture, the ruins are a great stop.

If you drive to Barboursville to see the ruins, don’t miss a chance to try the wine! Barboursville offers one of the most complete tastings we have found in Virginia, and with everything from sparkling to sweet there’s a good chance you will find a wine you love. They offer a great viognier, Virginia’s state grape, and the dessert wine Philéo is memorable for its delightful sweetness. Still, it’s Octagon that we return to every time. Not on the tasting menu, Octagon (and yes, the name bears a Jeffersonian tie-in!) blends Merlot, Cabernet Franc, Cabernet Sauvignon, and Petit Verdot into one of the finest red wines in the state—and the world. It’s our go-to bottle when we need a great wine to take to a party or open for a special occasion, and it’s a great choice for a special treat.

More Information:
Our Post: Make Mine Virginia Wine: Wineries to Visit in the Old Dominion

Charlottesville: Where to Eat

In a college town there is no shortage of great places to eat, but we have two that we love.

Thomas Jefferson statue
Thomas Jefferson
Michie Tavern

Established in the 1700s, Michie Tavern is the perfect choice if you are on a historic Charlottesville day trip. After being greeted by servers in period costume, guests are seated in one of the dining rooms and invited to visit the buffet. The buffet has plenty of traditional items from a time when the midday meal was the biggest meal of the day. Fried chicken, pulled pork, green beans, mashed potatoes, and biscuits are favorites, and don’t overlook the sweet stewed tomatoes—a favorite for most people with whom we have enjoyed a meal!

More Information:

Bodo’s Bagels

Real New York bagels in the middle of Charlottesville? No problem! Bodo’s Bagels is a staple for college students, and we love to make it a breakfast stop when we are in town. With a couple of locations including one on UVA’s “Corner” near the campus, bagels and cream cheese or bagel sandwiches are served hot with a crispy exterior and a chewy interior—just like you would expect from a New York bagel shop. An everything bagel with lox and cream cheese is my favorite way to start a Charlottesville day trip!

More Information:


Opened in 1976 by a graduate of the University of Virginia, Littlejohn’s has been a favorite of Charlottesville residents, UVA students, and tourists for more than 40 years! Littlejohn’s calls itself a “New York-inspired deli with a Southern sensibility,” and the sandwich shop has classics and specialty sandwiches for just about every craving. They have a great menu ranging from Reubens, Clubs, Italians, and flatbreads to special sandwiches named in honor of famous UVA alumni like retired NFL star Chris Long and NBA Hall of Famer Ralph Sampson. Littlejohn’s is located right on The Corner near the campus grounds, and it’s a great option if you’re looking for something quick and iconic in Charlottesville.

More Information:

Hotels in Charlottesville

Are you planning a trip to Charlottesville, Virginia? Here are some hotel deals to consider.

Enjoy Charlottesville!

Charlottesville, Virginia is an incredible place to explore history, and spending a day walking in Thomas Jefferson’s footsteps through Monticello and the University of Virginia is a great way to learn and relax.

Leave a comment below and let us know if you plan a trip to Charlottesville—and let us know what tips you have to share!

More Information:

Related Posts

Looking for more fun places to visit in Virginia? Check out these articles!

1 Day in Charlottesville, Virginia: a Walk in Jefferson's Footsteps

* From time to time, our travels are directly impacted by a service or company. This post includes our candid review of our experience at various locations in Charlottesville, Virginia. We selected these locations based on our own research and travel needs; we were not offered and did not receive compensation of any kind from them or any other party in exchange for our review. Learn more about our travel philosophy here.