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Welcome to the beautiful city of Charlottesville (Cville to the locals!), where history, natural beauty, and creativity come together to form the perfect weekend getaway! If you’re a history buff, you’ll love exploring landmarks like Monticello and the University of Virginia. And if you’re an art lover, you’ll find plenty of galleries, theaters, and music venues to indulge your passion.
But that’s not all! Charlottesville is also home to some of the best wineries and breweries in the region. The fertile land and pleasant climate make it the perfect place for producing wine and craft beer. So be sure to check out these establishments during your visit!
And let’s not forget about the food! Charlottesville has a thriving farm-to-table scene, with many restaurants using locally sourced ingredients to create fresh and delicious dishes.
No matter what you like—whether learning about history, enjoying art, or being in nature—Charlottesville has something extraordinary for your weekend getaway. Let the city’s charm make you happy as you have fun and make memories you’ll never forget. This guide will ensure that your weekend in Charlottesville will be full of exciting things to do and learn!
Best Things to Do in Charlottesville
Downtown Mall
Looking for the perfect blend of history, art, and entertainment? Look no further than the Charlottesville’s Downtown Mall!
The pedestrian-only area known as the Charlottesville Downtown Mall is a vibrant hub and the heart of the city’s cultural scene, dating back to 1974. Thanks to its many restaurants and shops, it’s a popular destination for tourists and locals. It’s the best thing to do in Charlottesville.
So, get ready to explore over 120 shops, about 30 restaurants (lots have outdoor seating), art galleries, different entertainment venues, and a farmers market on Saturdays – all along Main Street!
But the Downtown Mall offers more than a place to shop and eat. It’s also a place where art and culture come together. There are art galleries, places for shows, and events that change with the seasons. You might even witness art events, live performances, and street performers.
As the sun sets, the Downtown Mall transforms into a magical sight, with its twinkling lights and illuminated buildings creating an enchanting atmosphere, making it an ideal place for a romantic evening walk or a fun night out with friends. You can sit outside, listen to live music, or watch people as you relax in the plazas and open spaces.
Paramount Theater
The Paramount Theater, located in the heart of downtown Charlottesville, is an iconic and historic performing arts center. This iconic facility is known for its architectural grandeur and role in hosting various entertainment options, making it an essential part of the city’s cultural scene.
Since its opening on November 25, 1931, the Paramount Theater has held a unique place as one of the last remaining “movie palaces” from the golden age of cinema. Its splendid architecture, exceptional acoustics, and excellent views have made it a treasured space for Central Virginia’s community life for over eight decades.
The theater’s historical significance is further highlighted by its connection to Thomas Jefferson’s architectural influence in its neoclassical designs. As you step inside, you’ll be transported to an era of elegance and artistry, where modern performances seamlessly blend with timeless beauty.
The Paramount Theater offers an impressive variety of live entertainment, from captivating concerts and theatrical productions to dynamic dance performances, side-splitting comedy acts, enriching film screenings, and more!
IX Art Park
The IX Art Park in downtown Charlottesville is a vibrant and captivating community space that celebrates creativity, diversity, and community connection. This dynamic art park has earned a reputation as a hub of artistic innovation with its ever-changing and diverse collection of artworks.
As you step into the IX Art Park, you’ll find an open-air environment that is a versatile space that transforms to accommodate a wide range of events and activities, making it a true hub of cultural exchange and enjoyment. You’ll encounter sculptures, murals, and interactive artworks during your visit. All of these creations are brought to life by local and visiting artists.
One of the highlights within the IX Art Park is the enchanting indoor space known as the “Looking Glass.” This immersive art experience is a collaborative creation by numerous local artists. Stepping into the Looking Glass is like entering a fantastical forest and kaleidoscopic cavern, complete with interactive installations that dazzle the senses and awaken our inner child. There is a fee for this.
Throughout the year, the IX Art Park hosts various events that reflect its commitment to artistic expression and community engagement. Festivals, concerts, spoken-word poetry readings, and other gatherings bring people together to celebrate the power of art and creativity.
University of Virginia
The University of Virginia (UVA), located in Charlottesville’s heart, is a prestigious and well-known educational institution. UVA, founded in 1819 by Thomas Jefferson, the third President of the United States and the primary author of the Declaration of Independence, is also a UNESCO World Heritage Site, an honor given to only a few institutions in the United States.
The campus of UVA is a captivating blend of historic charm and modern advancement. The iconic Rotunda, designed by Jefferson himself, serves as the highlight of the university. It stands as a symbol of intellectual wonder and architectural brilliance, overlooking the sprawling lawn that extends like an inviting open book.
Visiting UVA offers the opportunity to dive into the university’s rich history and vibrant academic atmosphere. Joining guided campus tours will provide insights into the university’s unique combination of historical significance and innovative educational programs.
You can explore the beautifully designed Jeffersonian architecture, stroll along the Lawn’s serenity, and understand the various disciplines that flourish within its walls.
The Corner
The Corner is located across from the UVA campus, an eclectic business district combining specialty shops and eateries. If you’re feeling peckish after visiting the UVA campus, just follow the crowd of students and locals to The Corner. This is your opportunity to try Charlottesville’s famous Bodo Bagels, NY-style bagels. It’s a local institution! The Corner is one of the best places to eat in Charlottesville.
Charlottesville Breweries
Charlottesville is home to eight craft breweries. Visit Rockfish Brewing Company while exploring the pedestrian Downtown Mall. Try Decipher Brewing’s Snowball’s Chance Helles beer if you’re into clever names. As a NE IPA lover, I was excited to check out Starr Hill’s Ramble On. You’ll find a brewery that delivers terrific flavor regardless of your taste preference!
Jefferson Vineyards
Nestled in the heart of Charlottesville, Jefferson Vineyards is a remarkable destination that beautifully blends historical significance with a commitment to producing exceptional wines. The vineyard’s roots trace back to land purchased by none other than Thomas Jefferson himself in 1773, marking a connection to the past that is still celebrated today, making it unique among the 40 wineries in the area.
A visit to Jefferson Vineyards provides an opportunity to indulge in a pleasant wine-tasting experience. You’ll get to try a wide range of wines made right on the premises. The vineyard produces many wines, ranging from rich reds to crisp whites and delightful rosés.
They also offer guided vineyard tours for those seeking a more profound experience. These tours offer a deeper understanding of the journey from vine to wine, shed light on the vineyard’s historical roots, and highlight the terroir that contributes to the distinctive qualities of the wines they produce.
For just $10, you can receive a souvenir-tasting glass and savor the flavors of approximately 10 to 11 different wines. The tasting experience is enjoyable and educational, allowing you to discover the specifics and characteristics of each wine.
Monticello Wine Trail
Of course, visitors can explore even more vineyards that are also located along the Monticello Wine Trail. Use the interactive map of the Monticello Wine Trail to plan your visit. You’ll find a large variety of tasting rooms offering wine tastings. You should have a designated driver if you’d like to visit several vineyards. Several tour companies provide vans and drivers so you can relax without worrying about drinking and driving!
Each winery allows you to try the local wines in their tasting room. Many have food trucks available on weekends, so check their schedule online before you go.
Carter Mountain Orchard
Carter Mountain Orchard, located near Charlottesville, is a delightful haven for those seeking a genuine agritourism experience. The Orchard has a long history dating back to 1912, when it was established as part of the Chiles Family Orchards. It has become a cherished local favorite and nationally known destination for fresh produce and unique experiences.
One of the best things at Carter Mountain Orchard is picking your apples and peaches – depending on the season! This hands-on experience allows you to pluck ripe, delectable fruits directly from the trees, connecting you with the area’s agricultural heritage.
Before you leave, visit Carter Mountain Orchard’s Country Store, offering a treasure trove of farm-fresh delights. The store showcases the region’s natural bounty, from freshly harvested fruits and vegetables to homemade jams, jellies, and local honey. There are also baked goods, homemade treats, and other culinary delights. The apple cider donuts are a hit with all people.
They also offer guided tours. You can join tours to learn about growing apples, farming methods, and the remarkable history of the orchard. These tours give a better insight into the orchard’s inner workings, whether you’re interested in the science of fruit farming or the history behind the Chiles family’s heritage.
Monticello
Monticello, the former home of Thomas Jefferson, the third President of the United States and the primary author of the Declaration of Independence, is an important site and a UNESCO World Heritage Site. This well-known monument will help you understand this famous person’s life, ideas, and achievements.
What’s exciting about Monticello is the guided tour of the house itself. During this tour, you’ll get to see the rooms, hallways, and unique designs of the house. This will show you what Jefferson thought and his personal life.
Thomas Jefferson’s Monticello’s beautiful gardens will show how Jefferson loved plants and gardening. You can walk through his flower and vegetable gardens and see the different levels of land he designed.
Other buildings and displays at Monticello will help you learn more about the enslaved people who lived and worked on the farm by visiting the slave quarters. This will give you insights into the history of slavery and the different parts of Monticello’s history.
James Monroe’s Highland
At the location of the former home to James Monroe, the fifth president of the United States, Highland reflects the growth of the young country, too. Guided tours offer insight into what life was like inside these walls.
The 1818 Guesthouse exhibits blend the stories of those living here – free and enslaved people. Focusing on Monroe’s presidency, it explains how ideas at the time are reflected in present-day society.
Highland doesn’t shy away from addressing the ugly truth about enslaved people either. Monroe embodied contradiction, enslaving people (he only freed one in his lifetime) while calling for the abolition of slavery. The property addresses the prevalent attitudes of the time and how people sought to navigate them while slowly changing.
City Market
Charlottesville City Market is a bustling open-air market with a wide variety of locally crafted items, local produce, artisanal crafts, and a lively ambiance held from April to November. The market, which takes place every Saturday morning, attracts an outstanding crowd of over 100 sellers.
During your visit to the market, you may sample a wide range of fresh and locally grown fruits, vegetables, herbs, and other farm-to-table delights. This is a fantastic way to support local farmers while enjoying the pleasure of seasonal produce. In addition, the market offers artisanal and gourmet products ranging from baked goods and cheeses to jams, honey, sauces, and more. These foods usually highlight the region’s unique characteristics.
But Charlottesville City Market is more than just a food market; it is also a popular destination for handmade crafts, artwork, jewelry, textiles, and other unique goods local artisans create. This platform enables local businesses and entrepreneurs to exhibit their products and interact with the community.
The market’s offerings may change with the seasons, allowing a look into the area’s dynamic cycle of harvests and agricultural activities. Whether you’re looking for fresh vegetables, artisan items, or a vibrant community atmosphere, Charlottesville City Market is a place you should visit!
Charlottesville Distilleries
You’re in luck for those who prefer spirits to brews or wines, as Charlottesville has several local distilleries! If you’re walking downtown, check out Vitae Spirits. This family-owned and managed craft distillery makes award-winning standards like rum and gin. But it shines in its creative offerings with flavors such as Maple Cream Liqueur, Paw Paw Liqueur, and Strawberry Eau de Vie. They have created innovative cocktails, which they happily share on their website. On a hot summer day, Vitae Spirits sells adult freezer pops – perfect to help you cool down!
Skyline Drive
From Charlottesville, you’re only a 30-minute drive from one of the most picturesque drives in the eastern United States — Skyline Drive. It is the only public road that goes through the Shenandoah National Park. From Charlottesville, you’ll be at the southern end of the drive, which takes about three hours until reaching the northern end. You’ll enjoy beautiful views of the Blue Ridge Mountains.
Blue Ridge Parkway
Charlottesville is also a short drive from the beautiful Blue Ridge Parkway which cuts through the Shenandoah Valley. The scenic drive offers lots of pull-over areas worth visiting for gorgeous views. If you don’t want to go too far along the lengthy parkway, go to the Rockfish Gap, visible from Skyline Drive and the Blue Ridge Parkway and has one of the most amazing views, especially during fall leaf season!
Where to Eat in Charlottesville
Boylan Heights
Looking for the best burgers and shakes in town? Head over to Boylan Heights. Due to its popular location in The Corner, you’ll want to time your visit to avoid the crowds. But don’t worry if someone in your group is not a fan of burgers, as their extensive menu includes chicken and salads as well.
Michie Tavern
Established in 1784, Michie Tavern prides itself in serving food reminiscent of traditional Southern cuisine. Served buffet style, guests select from various foods, including vegetable soup, BBQ, mashed potatoes, collards, and beans. But the star? The fried chicken – seriously! This is the best fried chicken I’ve ever had – tender, crispy, and perfectly seasoned. Reservations are encouraged.
Where to Stay in Charlottesville
Luxury: Stays at the Inn at Court Square include homemade breakfasts. The beautifully decorated rooms are stylish and comfortable. The Inn is two homes together, one offering guest rooms and the other guest suites. Guests love their stay here.
Mid-Range: The Draftsman, Autograph Collection, is highly rated for its central location in downtown Charlottesville. It’s perfect for those who want to walk everywhere. I’m a fan of the Autograph Collection as I find them consistent in their high standards.
Budget: Fairfield Inn and Suites by Marriott Charlottesville Downtown/University Area is conveniently located next to UVA with easy access to downtown attractions. This newer hotel gets rave reviews about the friendly staff and breakfast offerings.
Final Thoughts on Things to Do in Charlottesville in a Weekend
Charlottesville is the typical college town except for its important ties to history. Because of the college, the city is constantly growing and developing. It is an incubator of innovation. The free Charlottesville Area Transit adds to the ease of visiting the city without always moving your car. Charlottesville VA is full of national historic landmarks and should not be missed!
I could see myself spending more and more time in Charlottesville, and you’ll see why when you visit, too.
Check out these other related posts:
- A Day Trip to Scottsville VA
- Harrisonburg VA: A Foodie Destination
- 20 Best Things to Do in Woodstock Virginia
Happy travels,
Annick, The Common Traveler
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Raised as a third culture kid living in South America and Europe, Annick caught the travel bug early. As an empty-nester, Annick enjoys sharing her tips for traveling for those with champagne taste and beer budgets.