Skip to main content
Try our new AI Powered Travel Planner
It's Free. Try it now!

Welcome to Charlottesville, VA – a charming blend of history, culture, and Southern hospitality. Located in the heart of Virginia, this vibrant city offers a plethora of activities to suit every taste. From exploring Thomas Jefferson’s architectural masterpiece, Monticello, to strolling along the historic Downtown Mall lined with quaint shops and restaurants, there’s something for everyone.

Hike the scenic trails of Shenandoah National Park or indulge in a tasting tour at one of the many local wineries. Whether you’re a history buff, outdoor enthusiast, or foodie, Charlottesville promises an unforgettable experience at every turn. Let’s dive into the top 15 must-do adventures!

(image via Wikimedia)

15. Monticello

View of plaque in front of Thomas Jefferson's historic home

Visiting Monticello is like stepping back in time to witness the genius of Thomas Jefferson firsthand. Perched atop a hill, this architectural gem offers a glimpse into the mind of one of America’s founding fathers. Explore the well-preserved rooms adorned with Jefferson’s personal belongings and inventions, stroll through the gardens designed by his own hand, and enjoy his impressive library.

Guided tours provide fascinating insights into Jefferson’s life and legacy, while the panoramic views of the surrounding countryside are simply breathtaking. A visit to Monticello is an enriching experience steeped in history and beauty.

14. University of Virginia

View of statue outside of University of Virginia

Steeped in rich history and architectural splendor, the University of Virginia (UVA) is a beacon of academic excellence and cultural significance. Founded by Thomas Jefferson in 1819, UVA’s iconic Rotunda and Lawn evoke a sense of timeless beauty. Attend a lecture by renowned scholars, stroll through lush gardens, or catch a game at Scott Stadium. With its prestigious academic programs, breathtaking scenery, and enduring traditions, a visit to UVA offers an unparalleled glimpse into the past, present, and future of higher education.

13. Downtown Mall

View of trees in the middle of downtown street

Downtown Mall Charlottesville beckons with its blend of historic charm and modern allure. Meander along the brick-lined pedestrian mall, flanked by trees and historic buildings turned bustling shops and eateries. Dive into a variety of unique boutiques, art galleries, and charming cafes offering a delightful array of local flavors.

Live music fills the air as street performers entertain, adding to the vibrant ambiance. Take a leisurely stroll or sip a cup of coffee al fresco while soaking in the lively atmosphere. Whether day or night, Downtown Mall Charlottesville promises an unforgettable experience brimming with culture and charm.

12. Shenandoah National Park

An expansive aerial view of the Shenandoah national park in autumn

Visiting Shenandoah National Park is a soul-stirring journey into the heart of nature’s grandeur. Located in the Blue Ridge Mountains of Virginia, this park boasts breathtaking vistas, cascading waterfalls, and forests teeming with wildlife. Hike along the iconic Appalachian Trail, where every turn reveals panoramic views that stretch for miles.

Immerse yourself in the tranquility of the wilderness as you spot deer, black bears, and a kaleidoscope of bird species. With over 200,000 acres of landscape to explore, Shenandoah offers endless opportunities for outdoor adventure, from scenic drives along Skyline Drive to camping under a canopy of stars.

11. Carter Mountain Orchard

Signs leading the way to Carter Mountain Orchard

Atop Charlottesville’s scenic Carter Mountain is an orchard that offers a delightful escape into nature’s bounty. With views of the Blue Ridge Mountains as your backdrop, journey through rows of apple trees. Pick your own apples or enjoy freshly baked goods and homemade treats at the rustic barn store.

Savor the taste of Virginia’s finest apples while sipping on freshly pressed cider or sampling award-winning wines from the onsite vineyard. Whether you’re seeking a family outing, a romantic date, or simply a serene retreat, Carter Mountain Orchard promises a Charlottesville experience in every bite.

10. Virginia Discovery Museum

View of the front of the Virginia Discovery Museum

(image via Instagram)

Step into a world of wonder at the Virginia Discovery Museum in Charlottesville. Catering to curious young minds, this interactive museum offers a hands-on learning experience like no other. Children can explore exhibits covering topics from science and nature to art and culture, sparking their imagination and creativity.

Engage in sensory play, experiment with water dynamics, or begin a make-believe adventure in the imaginative play spaces. With activities suitable for toddlers to tweens, the museum fosters a love for learning in a fun, exciting environment. A visit to the Virginia Discovery Museum promises laughter, discovery, and endless fun for the whole family.

9. Paramount Theater

View of seating under umbrellas in front of the Paramount Theatre

(image via Wikimedia)

Stepping into the Paramount Theater in Virginia is like entering a time capsule of grandeur and entertainment. Located in downtown Charlottesville, this historic venue exudes charm and elegance, with its lavish décor and ornate architecture. Originally opened in 1931, the theater has undergone meticulous restoration, preserving its Art Deco style while incorporating modern amenities.

From Broadway shows and concerts to film screenings and community events, the Paramount offers a diverse array of entertainment options for all ages. Whether you’re admiring the intricate detailing of the ceiling or immersing yourself in a captivating performance, a visit to the Paramount Theater is a truly memorable experience.

9. Ash Lawn-Highland

View of the old Ash Lawn-Highland building

Step into the past at Ash Lawn-Highland, the historic home of President James Monroe. Located among picturesque landscapes, this 535-acre estate offers a captivating glimpse into early 19th-century life. Wander through the beautifully preserved mansion, adorned with period furnishings and personal artifacts of the Monroe family.

Explore the gardens and grounds, where Monroe once walked and contemplated. Delve into the legacy of this Founding Father through guided tours and educational programs that bring history to life. Whether you’re a history enthusiast or simply seeking a tranquil retreat, Ash Lawn-Highland is a must-visit.

7. Montpelier

View of the front of an old historic building

(image via Editorial Adobe Stock)

Montpelier is the historic estate of James Madison, the fourth President of the United States. Stepping onto its grounds feels like a journey back in time. Explore the restored mansion, where Madison’s intellect shaped the foundation of American democracy. Wander through the gardens and immerse yourself in the rich heritage of this iconic site through guided tours, interactive exhibits, and special events.

6. Virginia Museum of Fine Arts

Aerial view of the grounds at Virginia Museum of Fine Arts at dusk

Step into a world of artistic wonder at the Virginia Museum of Fine Arts (VMFA). With over 50,000 pieces spanning 5,000 years of creativity, this cultural gem offers a captivating journey through human expression. Marvel at works by renowned artists like Picasso, Monet, and Warhol, as well as stunning collections of African, Asian, and European art.

Explore the museum’s dynamic exhibitions, from ancient artifacts to contemporary masterpieces, each telling a unique story. Engage in interactive experiences, educational programs, and special events that bring art to life for all ages. A visit to VMFA is an enriching adventure for the soul.

5. Skyline Drive

A round overlooking a beautiful valley and blue sky

Embark on an awe-inspiring journey along Skyline Drive, winding its way through the breathtaking beauty of Virginia’s Shenandoah National Park. Spanning 105 miles atop the crest of the Blue Ridge Mountains, this scenic drive offers panoramic vistas of rolling hills, verdant valleys, and cascading waterfalls.

Whether you’re an avid hiker, wildlife enthusiast, or simply seeking a tranquil escape, Skyline Drive has it all. Stop at one of the numerous overlooks to capture stunning photographs or set off on a hike along the Appalachian Trail. Fall in love with the majesty of nature as you explore this iconic American roadway.

4. Charlottesville City Market

Aerial view of the city market at sunrise

A visit to Charlottesville City Market is a delightful experience of the local culture and community spirit. Every Saturday, from April to December, this market comes alive with colors, aromas, and sounds. Nestled in the historic downtown area, it offers an array of fresh produce, artisanal crafts, and yummy treats from local vendors.

Sample homemade jams, pick up handcrafted jewelry, or simply soak in the lively atmosphere while enjoying live music performances. With its friendly vendors and diverse offerings, Charlottesville City Market is not just a market – it’s an experience that captures the essence of this charming city.

3. Michie Tavern

View of an old building with signs on the side

(image via Editorial Adobe Stock)

Stepping into Michie Tavern is like stepping back in time to Colonial America. This historic tavern offers a captivating glimpse into early American life. Visitors can savor hearty Southern fare served in traditional style, from fried chicken to savory stews, all while surrounded by the rustic charm of the tavern’s restored interior.

Explore the museum rooms filled with artifacts and learn about the tavern’s rich history as a gathering place for travelers and locals alike. With costumed interpreters adding to the ambiance, a visit to Michie Tavern is a delightful journey through history.

2. Scenic Drives

View of a narrow, winding road lined with wooden fences and trees

There are so many beautiful streets, lanes, and roads in Charlottesville that you can drive all day and not get bored. From Skyline Drive to the winding road taking you to James Monroe’s Ash-Highland, the views are unparalleled.

Journey through history and beauty as you gaze out your window for a relaxing ride around town.

1. Foxfield Races

View of a field and building

(image via Editorial Adobe Stock)

Experience the exhilarating tradition of the Foxfield Races in Charlottesville, VA. Every spring, this prestigious steeplechase event draws crowds for a day of high-speed horse racing, tailgating, and socializing. With its picturesque backdrop of rolling hills and lush greenery, the Foxfield Races offer a unique blend of sport and spectacle.

Attendees don their finest attire, from vibrant sundresses to dapper suits, creating a vibrant atmosphere of elegance and excitement. Whether you’re cheering on your favorite horse from the sidelines or enjoying gourmet picnics with friends, the Foxfield Races promise an unforgettable day of thrills and tradition in the Virginia countryside.




As you can see, Charlottesville has a lot to offer everyone. If you are looking to do more in the surrounding area, check out other weekend trips from nearby Charlottesville, Virginia.

These areas are perfect for a quick day trip or a long weekend getaway. Explore our favorite things to do or peruse some pre-built itineraries.

Related Reads

Jennifer Freehill

Howdy! I'm a vet and UniDeb graduate who's a passionate reader, writer, and data nerd. I tend to take life with a grain of salt, a lime, and a shot of tequila.