Last Updated on May 8, 2025
Charlottesville, Virginia, is a historic and vibrant city nestled in the foothills of the Blue Ridge Mountains, about 100 miles west of Richmond. Known for its rich history, beautiful landscapes, and intellectual atmosphere, it combines the charm of a small town with the cultural and educational offerings of a larger city.
Thinking of visiting this historic town? Here’s what to do during a weekend in Charlottesville.
Friday in Charlottesville
Visit Monticello
Spend the morning and early afternoon touring the house and grounds of Thomas Jefferson when you visit historic Monticello. With a variety of ways to spend your time at Monticello, the website offers several ideas for how to spend a half day or full day exploring the historic home of Thomas Jefferson.
The behind-the-scenes tour will give history buffs an in-depth view into Jefferson’s life and showcase all three floors of the home. A more condensed version of the tour is available, which lasts 45 minutes and is ideal for those short on time. The “From Slavery to Freedom” tour is 2.5 hours in length and invites guests to contemplate the enduring legacies of slavery and freedom. Tour ideas for those traveling with kids are available as well as tours featuring the beautiful grounds and view of the home.
Unwind at Jefferson Vineyards
No trip to Charlottesville is complete without trying one of the more than 40 wineries along the Monticello Wine Trail. Jefferson Vineyards is just down the road from Monticello, making it a great pit stop after a wonderful day exploring Thomas Jefferson’s home. During the springtime, guests can sip wine while relaxing to live music featured Fridays from 4-6 pm and Sundays from 2-4 pm. Grab an appetizer to tide you over until dinnertime when you visit The Vine, a seasonally inspired food truck.
Dinner at Fleurie
Treat yourself to fine dining after a long day of sightseeing when you visit Fleurie. Fleurie features a seasonal menu that rotates frequently and offers dinner guests a three-course menu for a fixed price of $135. With main courses featuring braised lamb, beef tenderloin, steak tartare, and roasted loberstail, just to name a few, guests rave and rave about this local eatery.
Saturday in Charlottesville
Brunch at Guajiros
If you’ve worked up quite an appetite from all the sightseeing you did on Friday, you’ll appreciate a hearty breakfast at Guajiros. Bringing the flavors of South Florida and Central America to Charlottesville, Guajiros brunch is one of the best-kept secrets for a wonderful brunch experience. Featuring popular brunch dishes like Huevos Guajiros, SoBe Avocado Toast, and Breakfast Tacos this place can’t be beat.
Shenandoah National Park
You can’t spend time in Charlottesville without checking out Shenandoah National Park. Located less than 30 miles from Charlottesville, Shenandoah National Park is exploding with cascading waterfalls, vistas, peaceful fields of wildflowers, and no shortage of spectacular sights. After breakfast, take a short drive to this magnificent scenic spot and take in a quick hike. We recommend Blackrock Summit Hike–an easy, yet very rewarding hike that takes just 45 minutes. Great for all ages and even pets, this short walk, rated easy on the difficulty scale, culminates in a viewpoint on top of a rocky talus slope with incredible views of the Shenandoah Valley, Massanutten Mountain, and beyond.
After your hike, cool down as you make your way through Skyline Drive, one of the most scenic and enjoyable rides in the country. It takes roughly 3 hours to drive the entire length and runs about 105 miles long as it winds along the crest of the Blue Ridge Mountains. Of course, fall is the most popular time to travel along the drive, but spring offers pretty pops of color throughout, thanks to colorful wildflowers as well as blooming azaleas and mountain laurel.
Dinner at Smyrna
Inspired by Aegean/Mediterranean cuisine, Smyrna’s executive chef Tarik Sengul uses only locally sourced ingredients for superior quality and taste. Located on W. Main Street, diners are in for a culinary feast, as head chef Sengul brings his fine dining experience from New York City to Charlottesville. Smyrna features an open kitchen experience designed to delight and entertain guests while they dine. Reservations are recommended.
Sunday in Charlottesville
Have brunch at Tiptop
In search of a traditional breakfast where “It’s all good?” Dine at Tiptop for brunch before exploring Charlottesville’s famous Downtown Mall.
Stroll the Downtown Mall
Charlottesville’s Downtown Mall is a pedestrian-only area that spans 7 blocks and is home to more than 3 dozen cafes and restaurants and over 120 shops. The center of Charlotteville’s art scene, you can watch a movie, play or take in live music at one of the several performance venues. You’ll feel like you’re back in time as you meander through the brick-paved walkway and visit shops and eateries all housed in historic buildings.
If Charlottesville, VA sounds like a place you’d love to be, let the experts at Howard Hanna find the right home for you.
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Allen Tate is the Carolinas’ largest real estate company with more than 70 offices and 1,800 Realtors in the Charlotte, Triad, Triangle, High Country, Upstate SC, Highlands/Cashiers and Asheville/Mountain regions. Allen Tate is a partner of Howard Hanna Real Estate, the largest privately held real estate broker in the U.S., with 480 real estate, mortgage, insurance, title, and escrow service offices and 15,000 sales associates and staff across 13 states. For more information, visit www.allentate.com and www.howardhanna.com.
Thomas Jefferson Monticello
Historic Downtown Mall
University of Virginia
Sanders Monticello Trail
Jefferson Vineyards
