A Weekend for Lovers of Learning

Written by Olivia Brown, Executive Director at Albemarle Charlottesville Historical Society

Explore Charlottesville's downtown area through a historical lens with this 2.5-3 day itinerary.

Day 1: Friday

Whether you’re arriving to Charlottesville after work or spending the day for a long weekend, there are always many great activities to check out!

An Afternoon at the Museum

Take a trip to Downtown Charlottesville and enjoy an afternoon of arts and culture! Located in a historic building that was formerly an elementary school, the McGuffey Art Center is one of the area’s oldest artist-run cooperative art centers. Their monthly First Fridays event welcomes people to see new exhibits, but their galleries are always featuring creative and beautiful artwork. Can’t make it for First Fridays? They have virtual events and interviews as well!

Looking instead for a way to get your kids into museums? A great alternative is to check out the Virginia Discovery Museum, open Monday – Saturday from 9:30am to 5:00 p.m. Their mission to foster intellectual curiosity and development in the children of our community makes for a great start to a meaningful weekend of learning and fun!

Dinner

While you’re downtown in Charlottesville, enjoy dinner on the historic Downtown Mall, celebrating its 50th year in 2026! There are numerous locations to choose from, but a nice dinner at the C&O Restaurant is never a wrong way to go. The restaurant itself is celebrating 50 years from opening its doors in 1976 but takes its name from the Chesapeake & Ohio Railroad that operated just across the street. The building that houses the French-style bistro is part of the former railway depot and since the 1920s has been known as a place to get a bite to eat, serving railway workers for many years while the railroad was in existence.

Day 2: Saturday

Breakfast

On Saturday morning, head to historic Downtown Charlottesville to start off with a coffee and pastry at Petite MarieBette on Water Street before walking to meet a historic walking tour guide with the Albemarle Charlottesville Historical Society (ACHS).

Walking Tours

Founded in 1940, ACHS has been a repository of local history for 86 years. With a research library full of archival treasures and small lobby exhibits to show off the museum artifacts, ACHS is dedicated to collecting, preserving, and sharing the history of Albemarle County and Charlottesville. Every Saturday from April through November, ACHS hosts regular public walking tours around the downtown Charlottesville area. There is something for everyone with three different tours available every weekend. Don’t want to decide? Take more than one and become the next expert on the city’s historic heart!

10am Court Square: Where Charlottesville Began Walking Tour
This tour showcases the origins of Charlottesville and its long history from the Monacan Nation to the modern removal of statues. Starting at the Albemarle County Courthouse on East Jefferson Street, you'll start in the earliest part of the County’s history, even before Charlottesville became the County Seat. You can learn about the fateful ride of Jack Jouett in 1781 to his father’s Swan Tavern, the construction of the Monticello Hotel in 1926, and the development of Court Square and Market Street Parks.

You’ll pass by some of Charlottesville’s houses of worship – including Charlottesville’s only synagogue, Congregation Beth Israel (founded in 1882), and oldest Catholic Church, Holy Comforter (founded in 1880) – to discuss how Jefferson’s support of religious freedom found its home in the city. Finish your tour by learning about the complex history of Paul Goodloe McIntire, a Charlottesville-born stockbroker whose legacy includes municipal parks and libraries as well as Confederate statues that have since made national news.

11:30am Historic Downtown Mall Walking Tour
Beginning just outside the Ting Pavilion and Charlottesville’s City Hall, this tour features old buildings and business and discusses the development of the city’s bustling Main Street. Explore how transportation changed from rivers to roads to railroads; the stories of immigrants, enslaved and free people of color, and many more who called this bustling downtown area home; and learn how the many storefronts and buildings have changed over time.

As you walk down what’s now a pedestrian mall, you learn how a city’s Main Street has the ability to change its landscape. Ghost signs and original buildings will be pointed out along the way, including the famous Miller’s Downtown, now known more for its connection to Dave Matthews Band, than its history as the drugstore started by Dr. Guy Miller, Sr. and Charles Link in 1916. No tour of the Downtown Mall would be complete without learning our more modern history, including the demolition of the nearby Vinegar Hill neighborhood and the subsequent construction of the pedestrian mall in 1976. Charlottesville’s complex history can be seen throughout its built environment – you just need to know where to look.

1pm Black Barbers of Charlottesville Walking Tour
Starting at the ACHS building and former public library, this tour shows that barbershops are not just a place for a haircut. You'll dive into the rich and meaningful history of Black-owned barbershops in downtown Charlottesville from the post-Civil War Era through Jim Crow and segregation and learn about influential community members like John West, who opened barbershops in the downtown area and spent many years serving a segregated city.

As locations of social activism and community gathering, barbershops were not only places of business for men like James Ferguson and William Cogbill, proprietors of two other downtown shops. Even take a peek at Cavalier Barbers, a Black-owned barbershop that’s been downtown since the early 2000s. Tours will include a walk off Main Street to visit the former site of Joker’s, located in Vinegar Hill, passing Tavern & Grocery along the way, a historic building formerly the site of George Inge’s grocery store. After the tour, walk with your guide back to the Downtown Mall for endless lunch options.

Lunch

These walking tours offer many opportunities to learn about Charlottesville and Albemarle history, but one great way to experience is through food! If you’re looking for an authentic meal that makes you feel like you’re stepping back in time, look no further than the deli lunch counter at Timberlake’s. Still using the original soda fountain and offering classics like malted milkshakes and triple decker sandwiches, Timberlake’s has existed since 1890 and been in its current location since 1917, making it one of the oldest restaurants in the city.

Afternoon in Scottsville

After lunch, head out of Charlottesville and to the original Albemarle County seat: the town of Scottsville. April through October, you can visit the Scottsville Museum. Admission is free and you will learn about the important history of this historic James River town. Serving as the county seat from 1744 until 1762, Scottsville plays a critical role in the development of Albemarle County and is still one of its most historic places. The Scottsville Museum tells of the town’s role in the Civil War, exhibits and tells Native American history, and shows how life has evolved and changed, just as the river has.

Want to try a local brew while you’re there? Located in a historic 19th century tobacco warehouse, check out James River Brewery to hear some live music or enjoy a beverage in their outdoor Beer Garden before heading back to Charlottesville!

Day 3: Sunday

Coffee and the University of Virginia

Start your morning on the early side by heading to Grounds at the University of Virginia. Established in 1819, there is more than 200 years of history to explore at Thomas Jefferson’s University. Grab a coffee on Elliewood Avenue at Grit and then walk over to the Rotunda to see an exhibit of historic artifacts in the Lower East Oval Room. You can explore the architectural features of the Lawn and see original artifacts from the early University. Before you leave, don’t forget to make your way up two more floors to visit the Dome Room, just like Queen Elizabeth II, Franklin Delano Roosevelt, and the Dalai Lama have all done.

After leaving the Rotunda, make sure to take a quick moment of reflection by visiting the Memorial to Enslaved Laborers, built to honor the lives and legacies of those who were enslaved at the University. Take their virtual tour to learn more about the individuals whose names are inscribed on the memorial, or read about its construction and process.

Brunch

Walking around UVA’s Grounds is sure to work up an appetite, and no better place for a Sunday brunch than heading back downtown to The Nook. Established in 1951, The Nook is another of the Downtown Mall’s staples. One of the oldest businesses in continual operation on the Mall, The Nook still boasts its original diner atmosphere. Though most Charlottesville natives may not even remember what was on this location before The Nook, it was previously a Masonic Lodge, a saloon, an auction house, and – farther back in history – a lot that had been owned by 5th President James Monroe.

An Afternoon Walk

End your weekend of learning and history with a stop at the Ivy Creek Natural Area & Historic River View Farm. With seven miles of walking trails, it’s the perfect way to blend the peace of nature with important stories of Albemarle County’s history. You can learn about the history of the Carr/Greer families and how Hugh Carr became one of the largest African American landowners in the county. Open on the weekends starting in April, the Barn is where the history of the families of River View Farm truly come to life through interactive educational displays. Take a short nature hike, see some wildlife, or hear inspiring stories as the perfect way to fight the Sunday blues.

Author

Olivia Brown

Executive Director of the Albemarle Charlottesville Historical Society