How to Spend 24 Excellent Hours in Charlottesville, Va.

Located a little over two hours from D.C. by car (or Union Station train), Charlottesville is the quintessential weekend getaway. Between its historic University of Virginia campus, gorgeous greenery of Shenandoah National Park, picturesque wineries, and intimate music festivals featuring some of the nation’s best bands, this sprawling section of Virginia has it all. Here’s a step-by-step guide to dining and drinking along the way during a quick overnight trip.

7 a.m.: Breakfast at Bodo’s Bagels

Virginia might not be known for their bagel prowess, but Bodo’s has a firm grip on the best bagel in town. Get a classic BEC (bacon, egg and cheese) on an everything bagel and marvel at the simple genius and efficiency in which the bagel-wich is made. When was the last time you got a freshly baked bagel for a buck?

ACTIVITY INTERLUDE: Hiking

The Shenandoah Valley has over 50 incredible hiking trails with spectacular wildlife. One must is Bear Church Rock (yes, there are bears) with breathtaking waterfalls spotted just a one-mile walk in.

10 a.m.: Carbs break at Cou Cou Rachou

A plush second breakfast feels right when it’s from Rachel De Jong, the French-trained former pastry chef at Michelin-starred Inn at Little Washington. De Jong dominates the savory and sweet over at beloved bakery Cou Cou Rachou. Grab several pain de printemps, a croissant-swirl of heirloom flour, local kale, and zippy local goat cheese. Pick up the homemade granola too; it’s surprisingly addicting with pops of citrus zest, salt, and zingy ginger.

ACTIVITY INTERLUDE: Polo playing

First-time polo learners (no horse-riding experience needed) can snag a lesson at the “Intro to Polo” experience at King Family Vineyards. The 1.5-hour class culminates with pours from the award-winning winery. Roseland Polo matches are held every Sunday at noon through October.

1 p.m.: Pit stop at Quality Pie

Charlottesville’s Mas Tapas alum Tomas Rahal began anew in 2018 with Quality Pie, bringing his commitment to local purveyors and his deep reverence for Spanish cuisine with him. The name might infer that this little red spot is just pizza and/or dessert, but that’s just some of its parts. Seasonal selections include Rahal’s mind-blowingly garlicky gambas de ajillo, which leave a 12-count shrimp implant on the brain. If his Spanish almond cake is available, it’s a must.

ACTIVITY INTERLUDE: Monticello Wine Trail

Named the 2023 Wine Region of the Year by Wine Enthusiast, the Monticello Wine Trail is home to 33 of the best vineyards in the Charlottesville region. Overwhelmed by all the grape goodness? Start with some on-site winemakers like Wisdom Oak, Michael Shaps, Pollak, and Gabriel Rausse.

Other options: Wander around the industrial-styled Wool Factory

5 p.m.: Cocktails at C&O Restaurant

This downtown gem, around since 1976, feels like a whole other world. Head to its downstairs bar to sip an expertly made gin martini while eyeballing a bar-side aquarium.

6 p.m.: Apps at Conmole

You can’t go wrong with any of Benos Bustamonte’s moles at Conmole. Bustamonte grew up in Oaxaca and maintains a loyal following for his rich and insightful moles. If you had to choose, the mole negro is resplendent in every way.

7 p.m.: Dinner at Smyrna

If you happen top be looking for a Joel Robuchon protege while in C-ville, you found one in chef Tarik Sengul at Smyrna. Located in the heart of the town’s historic district, Sengul combines his Turkish upbringing with Appalachian ingredients. His hearty turlu dish of cabbage and freekeh gets Virginia-fied with local Sharondale mushrooms. Manti, a Turkish ravioli of sorts, also gets the local mushroom treatment by way of their filling along with ricotta, loads of herbs, and tomatoes.

Plan B: Fleurie

If the reservation at Smyrna proves to be just a little tough to snag, Fleurie is an additional and excellent option. Chef Jose de Brito, another Inn at Little Washington alum, recently returned to the kitchen and brings big James Beard energy and contemporary French cuisine with him. Prix fixe dinner ($195 per person), which rotates regularly, recently featured a hefty hunk of foie gras with rich punch of walnut relish and delicate fish cakes (quenelles de brochet) mellowing in a deeply reduced cognac and lobster bath.

10 p.m.: Nightcap at Lost Saint

Hidden under American restaurant Tavern & Grocery, this brick-framed speakeasy surrounded in artsy oddities and taxidermy sends out well-made classic cocktails.

Other options: Live music and espresso martinis at Miller’s, late-night beers and burgers at divey Jack Brown’s (open until 2 a.m. on weekends)

Lodging:

Stay a little outside the city at the recently renovated 80-room Keswick Hall and give yourself a moment to pop in for snack at Marigold, helmed by the incredible Jean-Georges Vongerichten. Or hang in the center of it all at the wildly adorable South Street Inn, made up of 19 rooms in a restored mansion from 1852. For quaint vineyard vibes consider Crossroads Inn, which was bought and restored by the on-site owners of Pippin Hill Farm in 2022.

Keswick Hall/Facebook

—Tierney Plumb contributed to this report