Life in Charlottesville
New to Charlottesville or considering a move from DC, Richmond, or beyond? Many of our families have found Charlottesville to be a wonderful place to relocate, often choosing to stay in the area well beyond their child’s tenure at Oakland. With all the conveniences of city life amidst the splendors of the Shenandoah Valley and Blue Ridge Mountains, see what makes this award-winning city one of the best places to live and work in the country.
Visit the home of our third U.S. president, Thomas Jefferson, built for himself atop a mountain in his 5,000-acre plantation near Charlottesville. Tour the home and historic gardens, visit the president’s grave site, and explore the interactive exhibit dedicated to Sally Hemmings and other slaves, both freed and enslaved, that lived and worked at Monticello.
The Virginia Discovery Museum is a non-profit organization working towards sparking children’s creativity and giving them a welcoming space to discover and grow in the interactive museum exhibits. Offering after school discovery workshops and date night drop-offs throughout the year, the museum has great programming that kids of all ages (and parents!) can enjoy.
The Downtown Mall is one of Charlottesville’s most popular spots for live entertainment, eating, shopping, and personal wellness. Visit Miller’s, where Dave Matthews used to bartend and first performed, go to a concert at The Jefferson or Sprint Pavilion, and enjoy browsing all the fun, eclectic stores and coffee shops.
Sugar Hollow Trail is a premiere summer-time hiking and rock climbing destination with over eighteen miles worth of river crossings and plenty of swimming holes. Popular spots along the trail include Blue Hole, Turk Branch Trail, and the North and South Fork Moorman’s River trails.
The Rotunda is at the center of the University of Virginia’s original campus and serves as an academic, architectural, and social focal point of the University to this day. Take a tour and explore the basement exhibit showcasing artifacts from the early days of the University, many of which were uncovered during the recent Rotunda restoration project.
Designated as a UNESCO World Heritage Site, The Lawn is home to UVA’s Rotunda and Academical Village, which served as the school’s original campus when it was founded in 1819 by Thomas Jefferson. Today, the buildings are still functioning as they were over 250 years ago, and The Lawn has remained a popular spot for gathering and pictures.
Completely immerse yourself in nature in Pleasant Grove Park located in the heart of Fluvanna County. Explore over 20 miles of trails, visit the butterfly garden, or have fun with your dogs at the dog park.
The historic Corner has served as the center for socializing, eating, and living for Charlottesville residents and students since the University was founded. Eat at The Virginian, the oldest restaurant in Charlottesville, get drinks with friends at one of the many college bars, or pop into any of the small boutique shops for all of your UVA gear.
Catch a Virginia Cavaliers’ football game and cheer on the Hoos at Scott Stadium. Known for its beautiful architecture in the same neoclassical style that Jefferson used to design the Academical Village and Rotunda on The Lawn, Scott Stadium is a great place to watch a game or enjoy a concert with the whole family.
The award-winning John Paul Jones Arena is a popular concert and show venue in Charlottesville and is home to the Virginia Cavaliers basketball teams. Led by Coach Tony Bennett, UVA’s men’s basketball team clenched the NCAA Championship in 2019. Having hosted some of the biggest acts in entertainment, JPJ is known for not having a bad seat in the house and for giving a sense of intimacy despite it’s nearly 15,000-person capacity.
McIntire Park features 150 acres of botanical gardens, a golf course, children’s playground, skate park, walking trails, softball fields, and picnic areas for plenty of year-round family fun. In the spring, the park hosts the annual Dogwood Festival where attendees can enjoy a wide range of carnival rides and treats.
Go on a quest of your choice with family or friends at the CVille Escape Room where you’ll have to solve puzzles, find clues, and open locks to find your way out. Themes and rooms cater to all ages, so everyone can be a part of the fun.
Offering apple picking, hayrides, and a view that cannot be beat, Carter Mountain Orchard is a perfect family outing spot throughout the spring, summer, and fall. Popular signature events include the Thursday Evening Sunset Series, Cultivating Curiosity for kids ages 3-8, the Peach Festival, and the Apple Harvest Celebration.
The Sprint Pavilion is a popular outdoor concert and event venue located at the end of the Downtown Mall. This spot is especially known for its family-friendly Fridays After Five free concert event series where food trucks line up and local artists come to perform from April through September.
Enjoy a fun-filled day out with family and friends on the James River throughout the spring, summer, and fall. Take a self-guided trip by kayak, raft, tube, or canoe to float or fish along the river and rapids.
IX Art Park is a free creative space in an old industrial zone for local artists and kids to come leave their mark on the greater Charlottesville community. Walk through the sculpture garden with several interactive pieces, or come for one of the many concerts, festivals, and exhibitions that are constantly taking advantage of the park’s unique atmosphere.
Skyline Drive, also referred to as the “Gateway to the Shenandoah Valley,” encompasses over one hundred miles of roadway with the best views and scenic stops along the Blue Ridge Mountains and Shenandoah National Park. Featuring several large waterfalls, premiere hiking, plenty of picnic areas, and places to camp, Skyline Drive is full of opportunities for family fun year-round.
Go back in time to the colonial era in this historic tavern and antique shop. After you enjoy a lunch buffet or sit down dinner of traditional colonial fare, take a self-guided tour of the oldest part of the tavern or peruse the antique and metal shops that sell authentic colonial-area artifacts and replicas.
Highland Plantation, bought and built by James Monroe, the fifth president, is adjacent to Thomas Jefferson’s Monticello in Charlottesville and offers a unique view into colonial era plantation life and slavery at the time. Take a tour of the house and grounds or enjoy a walk down one of Highland’s scenic trails.
On Saturdays from April through December, the Charlottesville City Market features crafts, fresh produce, and yummy treats from local artisans, farmers, and small business owners. Whether you’re meeting up with friends or are looking for a fun outing for the whole family to enjoy, the market is a favorite Charlottesville spot.
Greenfield Farm is the perfect place for a fall family outing. Partake in all of your favorite autumn activities, including picking a pumpkin from the pumpkin patch, taking a hayride, walking through a sunflower field, finding your way out of a corn maze, meeting farm animals, and so much more.
Shenandoah National Park is over three hundred square miles of protected land that is home to diverse animal habitats, over five hundred miles of hiking trails, gorgeous waterfalls, and spectacular views from the Blue Ridge Mountains. This park is truly paradise for anyone who loves camping, fishing, hiking, or picnicking with friends and family.
A great place for birthday parties, summer camps, or just a rainy weekend day, Bounce Play-n-Create is a space for kids to bounce, paint, cook, crawl, climb, and slide year-round. Owned by an Oakland alumni family, it was voted Charlottesville’s favorite rainy day outing and party location; kids have a blast while parents relax and watch them have fun.
This indoor water park allows for year-round fun in always warm 84 degree water with water slides, lazy rivers, a wave pool, hot tubs, inflatable fortresses, and body slides for the whole family. Dubbed the second best water park in America by USA Today, kids and adults of all ages are sure to have a great time.
Wintergreen is a four-season mountain resort situated in the Blue Ridge Mountains right outside Charlottesville in Nellysford, Virginia. Throughout the year, take advantage of great skiing, tennis courts, a large spa, premium golfing, and a wide range of dining and lodging options.
One of Fluvanna County's biggest draws to the area is its abundance of idyllic and highly-acclaimed wineries. Parents, take time for yourselves and do some well-deserved winery hopping while in town.
Located on the grounds of UVA, The Fralin Museum of Art is home to rotating art exhibits throughout the year, giving UVA students and Charlottesville residents the opportunity to appreciate and learn about diverse collections of art. Their calendar of events offers several family-friendly learning activities free of charge year round.
Typical Travel Times by Car
From Washington, DC · 2.5 hours
From Richmond, VA · 1 hour
From Roanoke, VA · 2 hours
From Virginia Beach, VA · 2.75 hours
Charlottesville Albemarle Airport (CHO)
Offering 50 daily direct flights on American Airlines, Delta, and United, the airport makes getting to the area a breeze and is just eight miles from downtown Charlottesville.
A Goff Airport Shuttle Transportation
Camryn Executive Transportation and Limousine
Aiport Car Rentals
Local Office: 434-973-6000
Local Office: 434-297-4288
National Car Rental
Local Office: 434-974-4664
Local Office: 434-974-466
By Train or Bus
810 W. Main St.
Charlottesville Station: 434-296-4559
310 W. Main St.
Omni Charlottesville Hotel
212 Ridge McIntire Rd, Charlottesville, VA 22903
1309 W Main St, Charlottesville, VA 22903
Boar’s Head Resort
200 Ednam Dr, Charlottesville, VA 22903
701 Club Dr, Keswick, VA 22947
Angel Nest Bed and Breakfast
288 Fieldstone Dr, Keswick, VA 22947
Courtyard by Marriott Charlottesville - University Medical Center
1201 W Main St, Charlottesville, VA 22903
Residence Inn by Marriott Charlottesville Downtown
315 W Main St, Charlottesville, VA 22903
Fairfield Inn and Suites by Marriott Charlottesville Downtown/University Area
401 Cherry Ave, Charlottesville, VA 22903
Hilton Garden Inn Charlottesville
1793 Richmond Rd, Charlottesville, VA 22911
Comfort Inn Monticello
2097 Inn Dr, Charlottesville, VA 22911
1296 Clifton Inn Dr, Charlottesville, VA 22911
University of Virginia Children’s Hospital
1204 W Main St, Charlottesville, VA 22903
University of Virginia Health System University Hospital
1215 Lee St, Charlottesville, VA 22903
Sentara Martha Jefferson Hospital
500 Martha Jefferson Dr, Charlottesville, VA 22911
MedExpress Urgent Care
260 Pantops Center, Charlottesville, VA 22911
Links and resources are listed for informational purposes and convenience. No direct or implied endorsement by Oakland School should be construed.