15 Historic, Free & Fun Things To Do In Charlottesville VA

Located 100 miles southwest of Washington, D.C. in the Piedmont region of central Virginia, historic Charlottesville is known for its presidential history and prestigious university. There’s more to Charlottesville, VA than its history and college life though. Here are some of the best places to visit the next time you are in the area.

Things to do in Virginia- Monticello in Charlottesville Virginia

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  • Address: 931 Thomas Jefferson Parkway, Charlottesville, Virginia

Monticello was home to the third president of the United States and author of the declaration of independence, Thomas Jefferson.

Thomas Jefferson began designing this plantation home at the age of 26 after receiving the land it sits on from his father. He used the land which was originally 5,000 acres as a working farm to grow tobacco and wheat. The property has been designated a National Historic Landmark as well as a UNESCO World Heritage Site. 

There’s a United States coin that depicts Thomas Jefferson’s home on its reverse side. Can you guess which one? If you guessed the nickel, you are correct.

Monticello in Charlottesville Virginia

This neoclassical and Palladian-style plantation home built in 1772 sits on top of a 850 foot hill, which is appropriate because the name Monticello means “little mountain” in Italian. 

Jefferson is actually buried on the grounds in what is known as the Monticello Cemetery.

Monticello is now owned by the Thomas Jefferson Foundation which operates it as a house museum and as an educational institution.

University of Virginia in Charlottesville Virginia- UVA

University of Virginia

  • Address: 1827 University Avenue, Charlottesville, Virginia

The University of Virginia was also designed in 1819 by Thomas Jefferson and is a UNESCO World Heritage Site. Not only did Jefferson design the buildings but he also designed the original courses of study.

The University of Virginia has been rated as one of the most beautiful campuses in the United States and as one of the most beautiful college campuses in the world, but you’ll never hear students call it a “campus” but instead “the grounds.”

University of Virginia in Charlottesville Virginia

The Grounds of the University of Virginia were so designated by Jefferson himself as the home of the “Academical Village” where students and professors lived and learned together.

The central area of the grounds is known as the Lawn. The Rotunda is the most familiar building on campus and stands at the north end of the Lawn. This building was inspired by the Pantheon in Rome.

The public research university offers 121 majors. Some of the alumni include the founders of Reddit and CNET.

James Monroe House - Highland in Charlottesville VA

Highland (Formerly known as Ashlawn)

  • Address: 2050 James Monroe Parkway, Charlottesville, Virginia

Located next to Jefferson’s Monticello was the estate of the fifth President of the United States. James Monroe bought this estate in 1793 and lived there for twenty-five years. Monroe named this estate ‘Highland.’

Thomas Jefferson and James Monroe were close friends and Jefferson encouraged Monroe to buy this land adjacent to his. Over sixteen years, Monroe added stone cellars and a second story to the home as well as additional land. By 1825, he had to sell Highland to pay off his debt.

The historic home changed hands many times throughout the years and was also known as Ash Lawn. The house was eventually willed to the College of William & Mary, which was James Monroe’s alma mater. James Monroe’s Highland is on the National Register of Historic Places and has been featured on Bob Vila’s A&E Network and C-Span.

Downtown Charlottesville VA

Historic Downtown Mall

  • Address: E. Main Street, Charlottesville, Virginia

The Downtown Mall in Charlottesville is one of the longest pedestrian malls in the United States. The mall is eight blocks long and runs from 6th Street N.E. to Water Street. Located along Main Street, the Downtown Mall is designed out of brick and concrete.

Downtown Charlottesville is home to art galleries, shops, restaurants, and offices. On the east end, the pedestrian mall ends at an outdoor concert venue known as the Ting Pavillion while the west end extends to the Omni Hotel. Somewhere in between are the Paramount Theater and the historic Jefferson Theater. 

The mall along with several side streets are closed to traffic.

Mitchie Tavern near Monticello in Charlottesville VA

Michie Tavern

  • Address: 683 Thomas Jefferson Parkway, Charlottesville, Virginia

Michie Tavern was established in 1784 and was known as the social hub of the community. Back in its day it provided travelers with lodging, food, and drink.

Today, Michie Tavern is a collection of historic buildings that exude an ambience from the 18th century. These buildings include a restaurant, museum, and stores. The stores include The Metal Smith Shop, Tavern Shop, The Artisan Shop, and The General Store.

Kluge-Ruhe Aboriginal Art Collection

  • Address: 400 Worrell Drive, Charlottesville, Virginia

One of the best Indigenous Australian art collections in the world can be seen at The Kluge-Ruhe Aboriginal Art Collection in Charlottesville. Outside of Australia, it’s the only museum dedicated to Indigenous Australian art.

The collection consists of over 2,000 pieces and includes artifacts, prints, sculptures, photography, bark and acrylic paintings. It’s a great place to go to appreciate human diversity and creativity.

The building sits on land once owned by Thomas Jefferson. He named this section of land Pantops which means ‘all seeing.’ The museum is located at Pantops Farm in the Pantops neighborhood.

Jefferson Theater

  • Address: 110 East Main Street, Charlottesville, Virginia

For entertainment, check out the Jefferson Theater which is one of the major performing venues in Charlottesville. It was built in 1912 and is located in the center of the Historic Downtown Mall. 

The venue offers a variety of entertainment and special events. Some of their past musical performances include Luke Bryan, Parachute, Dierks Bentley, SOJA, and Edwin McCain. You can grab dinner and a craft beer downtown and walk to a show afterwards.

Boar’s Head Inn

  • Address: 200 Ednam Drive, Charlottesville, Virginia

Looking for a resort? Then head over to Boar’s Head Resort, once known as Boar’s Head Inn. Here you will find elegant rooms, dining, recreational activities, and a luxury spa.

There are many recreational activities to enjoy. Some of these include tennis clinics, golf, fitness classes, a trail system, and pickleball clinics. Other events include music in the Mill Room and movies and music on the lawn.

Boar’s Head Resort is owned by the University of Virginia Foundation and sits at the foot of the Blue Ridge Mountains.

Virginia Discovery Museum

  • Address: 524 East Main Street, Charlottesville, Virginia

Small children love the Virginia Discovery Museum. It’s a hands-on museum for children from newborn to eight years old. It offers interactive exhibits in science, art, and history.

The Virginia Discovery Museum consists of two galleries. The front gallery includes Amazing Airways, Flight Lab, Automoblox, Magnet Wall, Literacy Lounge, Construction Zone, Showalter Cabin, Sensory Studio, and Light Bright.

The Back Gallery consists of ABC Hallway, Creation Station, Sound & Music Studio, Post Office, Financial Fundamentals, Children’s Hospital, Bakery & Cafe, Discovery Farm, and Discover Outdoors.

Charlottesville Hotels

Jefferson Vineyards in Charlottesville Virginia
credit Jefferson Vineyards

Charlottesville Wineries

Jefferson Vineyards

  • Address: 1353 Thomas Jefferson Pkwy, Charlottesville, Virginia

Thomas Jefferson hoped that Monticello could be the birthplace of American wine. He encouraged his friend, the Italian winemaker Filippo Mazzei, to bring his skills to Virginia by giving him 193 acres of land to experiment with.

Today’s owners of Jefferson Vineyards planted the same land with new vines and offer several varietals, including Cabernet Franc and Petit Verdot. Wine tastings are available Wednesday through Sunday throughout the year.

Blenheim Vineyards

  • Address: 31 Blenheim Farm, Charlottesville, Virginia

Blenheim Vineyards is another winery that is one of 23 wineries along the Monticello Wine Trail. The vineyard was founded in 2000 by Dave Matthews of the Dave Matthews Band. 

Blenheim Vineyards is best known for their Petit Verdot. Some of the other grapes grown at the vineyard include Viognier, Merlot, Cabernet Sauvignon, and Chardonnay.

Parks and trails in Charlottesville Virginia

Trails around Charlottesville VA

Rivanna River Trail

  • Address: Woolen Mills Railroad Trestle, Charlottesville, Virginia

If you’re a fan of nature trails, but don’t want to venture too far outside of the city, check out The Rivanna River Trail. This 19.5 mile trail is a loop that circles around the City of Charlottesville. The trail is a combination of urban and wilderness. You can do part of the trail or all of the trail.

The trail passes through neighborhoods and connects six city parks. Along the way, you’ll pass through areas of hardwood forests, streams, creeks, a railroad trestle, and bridges. All sections are for hiking while only some sections can be used for mountain biking.

The best access to the trail is either in Riverview Park, Azalea Park, Jordan Park, or Quarry Park.

Saunders-Monticello Trail

Address: 931 Thomas Jefferson Parkway, Charlottesville, Virginia

For a shorter hiking trail, your best bet is the Saunders-Monticello Trail. This 4 mile trail of crushed gravel and bridges winds its way to Monticello and back. The trail is very accessible to cyclists, walkers, and those in wheelchairs.

The trail follows through the ravines and forests of Albemarle County with gorgeous views of the Blue Ridge Mountains. Parking is available at the foot of Route 53 and on Route 20. The trail is open to the public daily.

Carter Mountain Orchard

  • Address: 1435 Carters Mountain Trail, Charlottesville, Virginia

One thing you’ll definitely want to do at some point is to visit local farms for fresh produce and baked goods.

Carter Mountain Orchard is a great place to pick your own fruit or to just enjoy some beautiful views. Not only do they have an orchard, but they also have the Country Store and Bakery.

From the orchards, you can pick peaches, apples, and pumpkins. The Country Store and Bakery carries unique gifts, apple cider donuts, pies, cider, and apple butter. There is something for everyone.

They are open year round with live music events throughout the year.

Shenandoah Skyline Drive

Skyline Drive

Just a short drive outside Charlottesville is the lovely Skyline Drive. This scenic drive traverses the entire length of Shenandoah National Park, with viewpoints to stop and gaze at the spectacular scenery of the eastern foothills of the Blue Ridge Mountains. Nature lovers should keep an eye out for black bear, wild turkey, and deer along the road.

Charlottesville offers something for everyone. No matter what you decide to do, you should leave there with some wonderful memories.

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