Downtown Charlottesville, Virginia in winter, at night with Christmas lights.

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Experience the Magic of Winter in Charlottesville

By: TLP's Partners

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For those of us who look forward to winter—bundling up, enjoying crisp days, and cozying up by a crackling fireplace with warm beverages—Charlottesville and Albemarle County, Virginia, are calling. The Charlottesville area embraces this colder and quieter season, transforming into a winter wonderland of cozy wineries, cafés, and quaint shops. Known for its rich history, Charlottesville and surrounding Albemarle County offer seasonal experiences from December through February with plenty for visitors to enjoy.

Eat and Sip

A spread of food on a table at the Oakhurst Cafe in Charlottesville, Virginia.

No trip to Charlottesville and Albemarle County is complete without discovering the award-winning wine scene. At more than 40 wineries along the Monticello Wine Trail, enjoy cool winter temps kept at bay by roaring fires (indoors and out) and a bounty of culinary delights. With so much to discover and affordable winter rates, especially during weeknight stays, visitors will want to tuck in for the night and do it all again the next day. You’ll quickly discover why Wine Enthusiast named this area its 2023 Wine Region of the Year.

Far from the busy and bustling autumn months, this is the time to take advantage of 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 multi-coursed meal at a farm-to-table eatery downtown or beyond.

Enjoy the tantalizing treats of flaky pastries and baked goods at Cou Cou Rachou or MarieBette Café & Bakery. Both are guaranteed to start your day off on the right foot, with a healthy dose of carbs, sugar, and coffee. Then, gather around the hearth for a taste of the 18th century at the authentically preserved Michie Tavern to continue learning about Charlottesville’s past and present. 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. When dinner comes calling, a stop by the Dairy Market is a must. Located in a renovated historic dairy building between downtown and the University of Virginia, this food hall is Central Virginia’s first and boasts a wide variety of culinary flavors from around the world.

Activities to Explore

A couple enjoying the lights at the Boars Head Winter Wander in Charlottesville.

After a day of tasting and sipping, 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 Café 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 holiday tree in the heart of the city. Dip in and out of any of the dozens of boutique shops before or after stopping at one of the many singular restaurants along the way.

Afterward, head to the Boar’s Head Resort for an enchanting experience at the Winter Wander Trail of Lights, which runs from November to early January. Upon arrival, guests will be greeted by an incredible display of lights, accessible by a delightful lakeside stroll and perfect for capturing Instagram-worthy moments. On select nights, visitors will enjoy fireworks, a live drone light show, and even performances by winged dancers, making for an enchanting winter experience.

Where to Stay

A bedroom at the Oakhurst Inn in Charlottesville, Virginia.

Charlottesville and Albemarle County are home to a range of accommodations, including quaint bed-and-breakfasts, luxurious resorts, and getaway stays at a working winery. Visitors can experience all that the Charlottesville area has to offer during a winter stay, while enjoying fewer crowds and more affordable rates on lodging.

After exploring the light displays at the Boar’s Head Resort, 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 the sleek and modern Doyle Hotel downtown for a boutique experience. Visitors will especially enjoy the heated rooftop bar that gives a perfect view of the city below. Another unique boutique stay is the Oakhurst Inn. Guests can enjoy this quiet oasis tucked away near the historic University of Virginia and still have proximity to downtown. With a café on-site, long, slow mornings by the fireplace are likely.

Whether wandering into town for the day or an extended stay, enjoy Charlottesville and surrounding Albemarle County in true Virginia fashion.

Start planning your winter stay today at VisitCharlottesville.org