For the Ultimate Winter Escape, Set Your Sights on Charlottesville and Albemarle County

For those of us who look forward to winter—bundling up, enjoying crisp days, escaping the summer’s “out of school” crowds—Charlottesville and Albemarle County are calling. The Charlottesville area embraces the next season, transforming into a winter wonderland of cozy wineries, cafes, and quaint shops. Known for rich history, Charlottesville and surrounding Albemarle County offer seasonal experiences from December to early March with plenty for visitors to enjoy.

What To Do in Charlottesville this Winter

Wondering what to do in Charlottesville? Grab a bit at The Ridley, pictured: Three plates from the restuarant

Eat and Sip

Far from summer, take advantage of the smaller crowds in town by easily snagging a reservation at one of Charlottesville’s locally owned top spots. Find big flavor in this smaller city whether dropping in for a pick-me-up pastry or seeking a coursed meal at a farm to table eatery in downtown or beyond. 

For elevated Southern signatures, find a table at the Ridley, named for the first Black student to earn a doctoral degree from University of Virginia, Walter Ridley. Punctuate a meal of next-level cornbread, Cajun pastas, and classic steak cuts with fine cocktails and wine and craft beer from the surrounding county. 

Find a no-frills, downhome alternative at Mel’s Cafe. As a Charlottesville institution, the meat-and-three-style restaurant serves up any imaginable American comfort food. In the morning go for an omelet or come back later for classic liver and onions. For a sweet treat or a filling meat pie, track down the Pie Guy—a food truck that serves up on-the-go provisions around town—or stop by their storefront location by the university. Have time to stay a while? Drop into MarieBette Cafe & Bakery for seasonal pastries or to simply admire their artisanal bread.

Gather around the hearth for a taste of the eighteenth century at the authentically preserved Michie Tavern to continue learning about Charlottesville’s past and present. Wrapped in garland and red velvet bows, The General Store on the grounds has boutique home goods and gifts like Virginia-made soaps and pantry items. Make a reservation in the dining room, the Ordinary, for a buffet of Southern delicacies like fried chicken, mashed potatoes, and black-eyed peas to be enjoyed fireside.

Explore Charlottesville and Albemarle County

Family outside of a winery in Albemarle County

With the multitude of vines woven around Charlottesville and Albemarle County like a basket, it is fitting that anywhere you go, the wine motif is nearby, from a stemmed glass to a pour or a bottle shop. At more than 40 wineries along the Monticello Wine Trail, enjoy mild winter temps kept at bay by roaring fires (indoors and out), a bounty of culinary snacks, and even places to tuck in for the night and do it all again the next day. 

And after a day of tasting your new favorite wines, there’s plenty to do in town by way of shopping and seeing. Whether you prefer live music performances, orchestras, reruns of classic holiday films, or ballet, there is truly something perfect for everyone available at Charlottesville’s Jefferson Theater, Paramount Theater, and Southern Cafe and Music Hall. Charlottesville is known for its picturesque historic pedestrian Downtown Mall. Come winter, the traffic-free stretch is ornamented with holiday lights and a large Christmas tree to mark the heart of the city. Dip in and out of any of the dozens of shops before or after stopping at one of the 30-plus restaurants along the way. 

For those road tripping to Charlottesville and Albemarle County, take home one of the best souvenirs: local produce! All year long, the Farmer’s Market at IX Art Park is home to vendors ranging from local chocolatiers and vegetable purveyors to potters, bakers, and more. Bring a cooler and load up. While there, check out Virginia’s first immersive art exhibit, The Looking Glass

At the nearby Charlottesville City Market—the city’s oldest open-air market—find other seasonal produce and baked goods throughout the year. You might even be rubbing shoulders with the chef who prepared last night’s dinner. Be sure to check it out before it closes down at the end of December!

Where to Stay in Charlottesville and Albemarle County

Room at the Oakhurst Inn in Charlottesville

Charlottesville and Albemarle County are home to a range of stays whether you’re the bed-and-breakfast type, a sprawling resort, or looking for a getaway stay at a working winery. Outfitted with holiday decor and programming throughout the winter months, it’s hard to go wrong when choosing between staying in town or enjoying the countryside.

Light displays and food vendors transform the area’s only AAA Four Diamond Resort, Boar’s Head Resort, from mid November to early January during their Winter Wander celebration. After exploring the light displays, enjoy a suite, round of golf, and the spa, or dine at one of their top-notch restaurants like the seasonal, chef-driven Mill Room. 

Enjoy peppermint mocha lattes at Dinsmore Inn’s Farm Bell Kitchen while planning your jaunts around town. Centrally located near the University of Virginia, this small, intimate, bed-and-breakfast-style inn is a perfect launchpad into the rest of the city. 

Enjoy the sleek and modern Quirk Hotel in downtown for a boutique experience. Explore the art exhibits downstairs while waiting for a table at Quirk Cafe or at the Pink Grouse—the hotel’s signature restaurant with a game-forward menu perfect for winter. Likewise, the heated rooftop bar gives a perfect view of the city below. 

Another boutique stay is Oakhurst Inn, which formerly served as the home of a university professor. Now, guests can enjoy the suburbs of Charlottesville tucked away near the historic University of Virginia and convenient to downtown. However, with a cafe onsite, long, slow mornings by the fireplace are likely. 

Whether wandering into town for the day or an extended stay, enjoy Charlottesville and the surrounding Albemarle County in true Virginia fashion. Start planning your winter stay today at or by exploring the Charlottesville city guide.

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