Charlottesville in Winter

Don't let the dropping temperatures mislead you; Charlottesville still has plenty to offer over the winter months. We've selected some of our favorite events and local spots to help you plan your winter visit.  Enjoy a more personal experience at a local tasting room or cozy-up fireside with friends and family. You won't want to miss any of these memory-making moments so book today to enjoy some of our best rates! 


  • Winter Wander at the Boar's Head: Enjoy a beautiful lighted journey this winter at the Boar's Head. Running November - mid January, this is an experience you won't want to miss. Tickets are required
  • Holiday Farmer's Market: Charlottesville's stellar Saturday morning market gets a holiday twist during December. Shop local artisans for gifts and treats at the corner of 2nd and Water Street. You'll also find special events at the Wool Factory, First Street Fair, and Crozet Holiday markets. 
  • Wintergreen: Just outside of Charlottesville, you'll find Wintergreen Resort. There's fun for all with skiing, snowboarding, and tubing! 
  • UVA's Lighting of the Lawn: Affectionately nicknamed LOTL, this special event brings students and the community together for a night of A Capella, dancing, and a spectacular light show to wrap up the evening. You can also Livestream the show from the comforts of your home.
  • Jefferson Theater: The Jefferson Theater provides one-of-a-kind music experiences with excellent line-ups. Stay the night next door at the Jeff Hotel for a seamless evening!
  • The Southern: As a smaller music venue, The Southern gives music lovers an up-close interaction with their favorite bands.
  • UVA Basketball: Catch a men's or women's basketball game at JPJ for some excitement. 
  • Holiday Tours at Monticello: A special opportunity, Monticello offers select evening tours of the grounds and home complete with era-specific greenery and decor. Tickets are required.

Food and Beverage:


  • C&O: Enjoy an intimate dinner or a drink at the bar with friends at C&O.
  • The Whiskey Jar: Grab a classic, southern meal and your favorite whiskey from their large collection. 
  • King Family Vineyard: Featuring two indoor tasting rooms and knowledgeable staff, enjoy an afternoon in the foothills at King Family.
  • Kardinal Hall: This beer hall boasts family-style seating, shelves of board games, and a heated patio to bring together friends and family. 
  • The Local: Sit upstairs by the woodstove for a cozy evening of delicious comfort food, excellent staff, and great craft cocktails.
  • Three Notch'd Brewery: Just off the downtown pedestrian mall, Three Notch'd offers space for large groups and a great rotating tap list. 
  • Durty Nelly's: Hiding by the Fry's Spring Bridge, this local pub offers sandwiches, good beer, and musical guests.
  • Restaurant Week: Keep an eye out for updated dates! This event offers special menus at a great price point for some of Charlottesville's premier eateries.