Enjoy destination dining, local wine, history, and art in the vibrant mountainside city of Charlottesville

A weekend getaway itinerary for this energetic Virginia city at the foot of the Blue Ridge Mountains
Downtown Mall

Photo courtesy of Virginia Tourism Corporation

Nestled at the foot of the Blue Ridge Mountains near Shenandoah National Park, Charlottesville, Virginia, is perhaps best known as the home of two former presidents (Thomas Jefferson and James Monroe) and the University of Virginia. But beyond its presidential pedigree and handsome neoclassical campus, the city is an ideal location for a few days away, with a thriving restaurant scene, easy access to the bucolic countryside, and contagious creative energy. Here’s how to make the most of a weekend in this small town with big-city perks.


Check In
Your home base is the Quirk Hotel, Charlottesville’s first art-centric boutique hotel, opened in 2020. Located downtown on West Main Street, the hotel is steps from the city’s best shops and restaurants. Guest rooms, all featuring floor-to-ceiling windows overlooking either downtown or the Blue Ridge Mountains, are modern and just the right amount of fun, with pops of pink and creative design elements; each headboard, designed by Richmond abstract artist Kiki Slaughter, is a unique painted canvas. With five on-site bars and restaurants, an elegant lobby lounge, and an art gallery, the hotel is a destination in itself.

Quirk Hotel

Photo courtesy of Virginia Tourism Corporation

Start with a quick elevator ride up to the hotel’s Q Rooftop. Order the citrus-infused Pink Breeze cocktail and take in the mountain views before walking a few blocks to dinner at Oakhart Social. Exposed brick, reclaimed wood floors, and a wood-fired oven set the stage at this neighborhood restaurant everyone wishes they had back home. The vibe is unfussy yet elegant, with a seasonal menu of New American dishes meant to be shared. (Be sure those plates include the wood-fired oysters, hanger steak, and roasted Brussels sprouts, paired with a local Basic City Our Daily Pils.) End the evening at the Alley Light, a small, unmarked restaurant tucked into a side street (look for the lantern in the alley). Bar director Micah LeMon combines local fruit and foraged ingredients with his housemade bitters, syrups, and sodas to create mixology magic. Find a seat where you can in the low-lit space, pick your liquor, and ask for the Dealer’s Choice.

Oakhart Social

Photo courtesy of Virginia Tourism Corporation


Start the day at MarieBette, a Parisian-style bakery with two downtown locations. Order a croque monsieur, quiche of the day, or an assortment of pastries—think custard-filled canelés, buttery kouign-amanns, apple galettes, and chocolate almond croissants. Next, it’s the tour de farmers markets: First, head to Charlottesville City Market, where more than 100 vendors offer local produce and cheeses, homemade kimchi, handcrafted knives, and pottery. Then cross the railroad tracks to the Farmers Market at IX Park. Once a textile factory, IX is now a wonderland of murals, sculptures, restaurants, and on Saturday mornings, more than 60 farmers. Peruse the local goods, then step inside the Looking Glass, where local artists have converted a 6,000-square-foot warehouse into Virginia’s first immersive art space, which includes a multi-level tree house, interactive soundscapes, and opportunities for art-making.

One of the most vibrant pedestrian shopping centers in the nation, Charlottesville’s Downtown Mall brims with more than 120 shops and 30 restaurants, most with outdoor seating. Have lunch amid pots of flowering geraniums at Bizou, where chef Vincent Derquenne serves comfort food with a French accent. Order the meatloaf or fried chicken sandwich, but save room for grilled banana bread with ice cream and caramel. Next, shop for local gifts, handcrafted soaps, and unique home decor at O’Suzannah and browse New Dominion Bookshop for signed copies of local author John Grisham’s latest work. Then head a few blocks over to McGuffey Art Center, an artist-run co-op in a historic elementary school building. Tour the gallery and peek into any open studios; there’s a good chance the artist will invite you inside. Energy to burn? Make the short drive to the restored historic Wool Factory, where you can walk along the Rivanna River at nearby Riverview Park and enjoy an Italian-style pilsner at Selvedge Brewing.

Wool Factory

Photo courtesy of Virginia Tourism Corporation

Dinner is at Tavola, a cozy trattoria serving rustic Italian fare in the vibrant Belmont neighborhood. Start with the burrata or fried artichokes and a negroni from the cicchetti bar while soaking in the warmth of the intimate space. You can’t go wrong with anything on chef Michael Keaveny’s locally sourced menu, but his linguine alla carbonara will prove hard to resist (so don’t try). After dinner, head back downtown to the Milkman’s Bar, located in the recently restored Dairy Market food hall, built in 1937 to house the Monticello Dairy company and now hosting more than 18 restaurants and shops. Embrace the nostalgic soda fountain vibe and order the Big Tickle, an egg cream made with bourbon and amaro, and enjoy the buzzy atmosphere. End the evening with live music at Miller’s Downtown, where part-time local Dave Matthews once tended bar; jazz is on tap most nights, but you never know who might drop by.

Dairy Market

Photo courtesy of Virginia Tourism Corporation


A visit to Charlottesville is not complete without seeing the University of Virginia, a UNESCO World Heritage site designed by Thomas Jefferson. Start at the Rotunda, modeled after the Pantheon in Rome, and walk the Lawn, where students live alongside professors in the original brick dormitories. Nearby, see the recently constructed Memorial to Enslaved Laborers. Unveiled in 2020, its two engraved granite rings acknowledge and honor the 4,000 or more individuals who built and maintained the university from its beginnings in 1817 until the end of the Civil War. Your last stop is perhaps the most famous Charlottesville destination of all: Bodo’s Bagels. Go to the location on the UVA Corner (the hub of university nightlife, on University Avenue near Elliewood Avenue), order a Deli-Egg (an omelet filled with diced meat and cheese) on Everything, and consider yourself a local.

University of Virginia

Photograph from Shutterstock

The Charlottesville area is home to more than 40 wineries and a flourishing community of craft breweries and cideries. Start with these, all within a half-hour drive from downtown.

Grape Escape
Sip a glass of award-winning rosé on the lawn at King Family Vineyards, where the mountain view is center stage and free polo matches take place most Saturdays.

How ’Bout Them Apples
Order an effervescent Farmhouse Dry at Potter’s Craft Cider, which sources heirloom apples from nearby farms and is housed in a 100-year-old stone church.

Good Brews
Play some cornhole, listen to live music, and most importantly, order a Chapter 2 IPA and settle into an Adirondack chair overlooking the North Fork River at the Brewing Tree Beer Company.

This article appears in the Spring & Summer 2022 issue of Southbound.