21+ Outstanding Things To Do in Charlottesville VA

Whether your fascination with Charlottesville, Virginia, is based on its historical significance, its position beside the Blue Ridge Mountains, or something else entirely, this medium-sized city might just impress you.

Exploring some of the country’s most famous, and sometimes notorious, historical sites or traversing the many wineries (or both) could await you in this charming Virginia city literally built on top of Americana. 

Here are 21+ things to do in Charlottesville VA that you shouldn’t miss!

COOLEST PLACES TO STAY IN CHARLOTTESVILLE

• Best Historic Option. Inn at Court Square is a small boutique hotel where you’ll discover two beautifully restored historical and architecturally relevant houses. Built in 1785, the federal period house is the oldest existing house in historic downtown Charlottesville.

• Best Downtown. Omni Charlottesville Hotel is adjacent to the historic downtown Pedestrian Mall. This gorgeous hotel blends the area’s unique history with modern luxury. It features a seven-story glassed in atrium lobbyand one of two heated pools.

• Best Budget Option. The English Inn of Charlottesville is affordable but well-rated, and steeped in British tradition. This hotel also has an indoor pool and complimentary breakfast making it a great choice for families.

MONTICELLO

Discover whatever it is Thomas Jefferson did in Monticello (we hope some of you understand this “Hamilton” reference) by visiting his famous home. See the manor as it may have been in Jefferson’s time, or explore the farm and gardens that surround it while learning about how he and his family lived at the top of America’s history.

Monticello is a National Historic Landmark, and together with the University of Virginia is designated as a UNESCO World Heritage Site. After you’ve visited Monticello, make sure to take a look at the back of a nickel!

Also, take some time to learn about the over 400 enslaved people who lived and worked on the Monticello property. Take in the actual history of Sally Hemings, whose history was often diminished in the wake of what we know about Jefferson. Much of Monticello’s exhibit on Hemings is actually taken from the words of her son, Madison Hemings, who was one of Jefferson’s sons.

SHENANDOAH NATIONAL PARK 

Nearly 200,000 acres of natural wonder await you in the Shenandoah National Park. Not only can you experience the beloved Shenandoah Valley, but you can also see the Appalachian Trail, as well as the magnificent Blue Ridge Mountains. John Denver may have been singing about West Virginia, yet the same Blue Ridge Mountains might have you humming “Country Roads” when you see them.

With so much park to see, a drive in Shenandoah National Park via Skyline Drive is a great opportunity to take a scenic drive. This National Scenic Byway takes visitors through Shenandoah from the comfort of their personal vehicles. When you need a rest, there are plenty of places nearby to rest up for another day of mountainous adventures.

A visit here is one of the best things to do in Charlottesville VA!

MONTICELLO WINE TRAIL

What has come to be known as “The Birthplace of American Wine,” the 40 wineries of the Monticello Wine Trail take wine very seriously. Inspired by Thomas Jefferson’s love of winemaking and vineyard tending, these wineries maintain the Charlottesville area’s penchant for the craft. All of the wine trail members are within 25 miles of the Charlottesville metropolitan area, so it’s easy to make a stop at a few during your trip. (We won’t tell if you stop at more than a few.)

By the way, Virginia Wine Month is celebrated every October — in case you needed a reason to go.

SAUNDERS-MONTICELLO TRAIL

Running along the Thomas Jefferson Parkway, the Saunders-Monticello Trail features nearly 90 acres of preservation that leads towards the home at Monticello.

Although it’s roughly four miles, the trail is handicap accessible. Hours when the trail and park grounds are open vary, depending on the season and holidays.

CARTER MOUNTAIN ORCHARD AND COUNTRY STORE 

Head down the street from Monticello, or a few minutes outside of downtown Charlottesville, and you’ll stumble upon Carter Mountain Orchard and Country Store. This vineyard and fruit orchard has been a community favorite for years, and not just during apple season either. Because their offerings depend on what’s in season, there is always something new to enjoy at Carter Mountain.

Also on the premises is Bold Rock Tap Room, which serves craft hard ciders and seltzers made from the orchard’s apples. On top of that, Carter Mountain has its very own wine shop, not to mention the apple butter and cider donuts. We could live on cider donuts.

MICHIE TAVERN

With a history dating back to 1784, Michie Tavern is a living embodiment of Virginia’s history.

Michie’s is named for its founder, Corporal William Michie. The 1784 Pub within Michie Tavern is like stepping back in time to experience what barflies of old might have experienced here, grasping their mugs of ale.

You can even try your hand at a Colonial bar game while you’re here.

THE LOOKING GLASS

If this name makes you think of “Alice in Wonderland,” you might be partly right — at least aesthetically. The Looking Glass is Virginia’s first immersive art experience that will make you feel like you too have fallen down a rabbit hole.

Part of the Ix Art Park, this artful space was curated with local artists to put you right into the art. It is safe and fun for all ages and the art park suggests at least an hour to experience The Looking Glass fully.

KEMPER PARK

In conjunction with the Saunders-Monticello Trail, Kemper Park is also part of the larger Monticello property in Albemarle County.

With hiking trails, an arboretum filled with native plantings, and a pond, this park is a place where one can just relax or go for an adventure. From the Carter Overlook, you can see panoramic views of the city of Charlottesville, as well as the neighboring Blue Ridge Mountains.

KLUGE-RUHE ABORIGINAL ART COLLECTION AT THE UNIVERSITY OF VIRGINIA

The only museum outside of Australia dedicated to Indigenous Australian Art, the Kluge-Ruhe Aboriginal Art Collection at the University of Virginia makes Charlottesville a more special place. Most of the collection at the museum was collected, curated, and commissioned by John W. Kluge and Edward L. Ruhe, who then left their collections to the university. 

Temporary exhibits come through the museum throughout the year, bringing new varieties of aboriginal art with them. Past exhibitions have included With Her Hands: Women’s Fiber Art From Gapuwiyak and Ngunguni: Old Techniques Remain Strong.

Visitors can walk through the museum on their own or take a free tour with docents to learn more. Longer or more specialized tours can also be booked for a fee with the museum. 

ALBEMARLE BAKING COMPANY

Right on Main Street in Charlottesville is an award-winning bakery that was so well received by the community it had to get a bigger space in 2001. Albemarle has been feeding the masses in Charlottesville since 1995 with their scrumptious goodies.

Their offerings change throughout the week, so if you fall in love with that Apple Cinnamon Cranberry bread you saw at the bakery, you might want to snag it. 

RAGGED BRANCH DISTILLERY

Thomas Jefferson warns us in “Hamilton” not to mess with Virginia’s whiskey, and with a taste of the bourbon from Ragged Branch Distillery, you might find out why.

The grains they distill into their bourbon are grown by Ragged Branch, so they know that their whiskey is quality. There’s a reason their bourbons are award-winning.

JAMES RIVER BATTEAU CRUISE

Per the James River Tour site, the James River Batteaux were flat-bottom boats designed to navigate the shallow rivers of Virginia, specifically the James River. In that spirit, the James River Batteau Cruise Co. introduces guests to this type of boat they might not be familiar with in honor of that historical element.

This cruise company is the only one that offers a sunset cruise on the middle James River, while they also offer midday tours and private charters as well. You can even take a dip in the river during the cruise if you want to. 

THE MARKET AT GRELEN

A dreamy European-style shop awaits you at The Market at Grelen. Surrounded by foliage, you can pick your own fruit, enjoy a farm-to-table lunch, take off on one of Grelen’s trails or kick back with some hard cider.

The market itself resides on a 1000-acre tree nursery, so the views are tremendous. When you inevitably fall in love with the property, you can also stay at one of their lodging venues.

VIRGINIA DISCOVERY MUSEUM

As Charlottesville’s children’s museum, the Virginia Discovery Museum gives kiddos the opportunity to get hands-on with their learning. Founded in 1981, this museum has become a part of the childhood landscape of the city.

Fifteen exhibit galleries divide up the programming into categories based on age. The Sensory Studio, for example, is a quiet space where the littlest learners can explore at their own level, while The STEM Lab: Automoblox area can house older kids building their own slot cars. 

You’ll also find special events here throughout the year.

HISTORIC DOWNTOWN MALL

Charlottesville’s downtown area is largely comprised of the Historic Downtown Mall. With a collection of over 120 shops and nearly three dozen restaurants housed in historic buildings, it’s almost impossible not to stop here, even if you don’t realize you’ve found it!

Live events are always happening around the mall, several galleries and museums live here, and you can even enjoy some pampering while you’re exploring! We’d have an easier time listing what you can’t find here rather than what you can.

JEFFERSON VINEYARDS

Grown on the same land that was once Virginia’s first wine company, Jefferson Vineyards is a continuation of the vineyard started by Thomas Jefferson. Since 1981, Jefferson Vineyards has been growing and producing award-winning products in the spirit of Thomas Jefferson’s passion for wine. They are dedicated to conservation practices around their property. 

The land on which it sits was given from Thomas Jefferson to Philip Mazzei in 1773. The original home was taken apart in 1939, with some of its exterior going to renovate the Michie Tavern, but the Woodward Family rebuilt the Colle in 1939. Guests can stay in the historical home at Jefferson Vineyards that sleeps ten. 

POTTER’S CRAFT CIDER TASTING ROOM

What began as the dream of two friends, Tim Edmond and Dan Potter, became a cider business. Potter’s Craft Cider Tasting Room is known for its house-made cider, live entertainment, and casual atmosphere.

Their tasting room was established inside a former church that then became an artist residence, which gives this hang a historical flavor to match their locally-sourced hard ciders.

JAMES MONROE’S HIGHLAND

Thomas Jefferson might be the most well-known politico to call Charlottesville home, but he’s not the only president. James Monroe, who served as the 5th United States president to Jefferson’s 3rd, lived at Highland. The property is now part of William & Mary, though it is still accessible to the public as a way to memorialize Monroe’s half a century of public service.

Neighboring property to Jefferson’s Monticello, Highland is also full of historical significance. Experts are still discovering historical elements around Highland, including ways in which the home has been renovated through the centuries. These discoveries become part of the narrative of the property that guests can learn about when they visit. 

Also like Monticello, Highland kept an unknown number of enslaved people on its property. Learning about the enslaved people while seeing Highland is one way to honor the history of the place, while also contextualizing the fuller picture of Monroe as a person, and not just as a previous president.

THE PARAMOUNT THEATER

Part of the Downtown Mall in Charlottesville, the Paramount Theater has stood as an Art Deco masterpiece since it opened in 1931. One of the country’s last “movie palaces,” Paramount continues to dazzle crowds time and time again. Though occasionally used for films, it is more often utilized as a live performing arts space throughout the year.

Live music, Broadway performances, visiting educational programs, like those with National Geographic, and so many more offerings take the stage at the Paramount. Like many other ornate theaters around the country, the community is keeping this space alive for future generations. 

FRALIN MUSEUM OF ART AT THE UNIVERSITY OF VIRGINIA

As an art gallery, the Fralin Museum of Art in the Thomas H Bayly Memorial Building at the University of Virginia holds an incredible array of work in its collection of almost 14,000 pieces. Their collection specializes in work such as Native American art, European and American paintings, African art, Asian art, and Pre-Columbian art. Founded in 1935 as the University of Virginia Art Museum, this space has contributed greatly to students and the public alike.

Roughly ¼ of the museum’s collection can be viewed online, which is one way they are growing the accessibility of their work. In addition to their permanent collection, visiting exhibitions keep the museum’s guests coming back for more. Previous temporary exhibits have included Unexpected O’Keeffe: The Virginia Watercolors and Later Paintings, A Painter’s Hand: The Monotypes of Adolph Gottlieb and Ansel Adams-A Legacy.

GLASS PALETTE INTERACTIVE GLASS ART STUDIO

Glass art can be an intimidating project to begin, especially if you’ve never worked with glass before. But with a studio like Glass Palette Interactive Glass Art Studio, there is nothing to fear. Maria DiMassimo and Cara DiMassimo will help you find your way into art-making in no time. 

Located in downtown Charlottesville, they hold walk-in projects, as well as classes, camps, and private parties too. Certainly a happy departure from the frequent wine and painting classes that became a trend for a while, Glass Palette provides something extra special. Make a gorgeous, slumped bowl or a pair of fused glass earrings — you can’t really go wrong with stained glass art. 

(Believe me, my mother is a stained glass artist. These kinds of projects always turn out cool.) 

WHERE TO STAY: KESWICK HALL

Boutique hotels get a new style with a luxury resort like Keswick Hall. From the cuisine at Marigold from acclaimed chef Jean-Georges Vongerichten, to a golf course surrounded by gorgeous landscape, Keswick is a step into bliss. The 1912 property has been lovingly renovated back to its splendor. 

Complete with views of the Blue Ridge Mountains, Keswick is as serene as it seems. Plus with less than 100 guest rooms, you’ll never be overrun by other visitors. 

Book It: Keswick Hall

THINGS TO DO IN CHARLOTTESVILLE VA FAQ

Is Charlottesville VA worth visiting?

Charlottesville, VA, is definitely worth a visit! In addition to being home to massive estates, you’ll also find plenty of outdoor recreation, family friendly activities, history, amazing restaurants, golf, and so much more.

Is downtown Charlottesville walkable?

Charlottesville’s Downtown Mall is definitely walkable. The brick pathways and historic buildings that house shops and restaurants make strolling the Downtown Mall a super fun activity.

How close is Charlottesville to Virginia Beach?

It takes a little less than 3 hours to get to Virginia Beach from Charlottesville. It’s easy to take a day trip to Virginia Beach from Charlottesville, and enjoy water activities and more!

MORE INFORMATION FOR YOUR TRIP TO VIRGINIA

• YOUR VIRGINIA VACATION
• VIRGINIA BEACH: 21 Amazing Things To Do In Virginia Beach, VA
• RICHMOND: 17 Things To Do In Richmond VA On Your Next Visit
• WILLIAMSBURG: 21 Phenomenal Things To Do In Williamsburg VA

WHERE TO STAY IN CHARLOTTESVILLE VA