1) Curl Up at a Cozy Winery

Experience the Monticello Wine Trail, Wine Enthusiast’s 2023 Wine Region of the Year, during the coziest season! In fact -- we made a list of 10 Cozy Wineries you need to visit this winter. Stay warm on King Family Vineyards' enclosed patio, enjoy firepits and mulled wine at Eastwood Farm and Winery, or enjoy unlimited s'mores at Merrie Mill Farm & Vineyard -- there are plenty of options!

2) Attend Wine Fest

*Advanced Tickets Recommended*

Wine Festival

The Wool Factory at The Historic Woolen Mills

Mark your calendar for Wine Fest on Saturday January 18th at The Wool Factory! Meet 18 different winemakers and wine projects from across Virginia with more than 35 wines & ciders to try. Food will be available for purchase. Get your tickets in advance here. A true celebration of Virginia’s small-batch wine and cider projects -- in partnership with Ethos Wine & Tea!

3) Attend Albemarle Ciderworks' Annual Wassail

FREE, Family-Friendly Event

Annual Wassail Celebration

Albemarle Ciderworks

Wassail is both a warm, cider beverage and a traditional, English celebration of drinking and singing the health of the Orchard! Join Albemarle Ciderworks on Sunday, January 12th as they revive ancient festivities and salute the trees with toasting, music, cider and more! More info on events and scheduled activities here.

4) Attend a UVA Basketball Game

College basketball season is in full-swing and January is a great chance to catch a game at John Paul Jones arena! Both UVA men’s and women’s teams have tickets available for games throughout the month. Wear your orange and navy blue and get ready to cheer for the Hoos!

No home games while you're in town? No problem! The Paramount Theater will be screening several out-of-town matchups. More info here: https://www.theparamount.net/events/

5) Embark on a Group Gravel Ride

Take the chance to cycle the beautiful countryside surrounding Charlottesville and Albemarle County with Blue Wheel Bicycles Group Gravel Ride on January 12th.

All abilities are welcome! However, riders should be prepared to complete the designated mileage of unpaved and paved roads without support. Riders are responsible for their own navigation, so please buddy up, know the route, and bring your own food, water and spare tube. Additional Group Gravel Rides are scheduled for February 2nd and March 9th.

Explore more Road & Gravel Rides on our Trails & Outdoor Routes page.

6) Attend Charlottesville Restaurant Week

Mark your calendar for Charlottesville Restaurant Week happening Monday, January 27th – Sunday, February 2nd. Choose from a $25, $35, or $45 three-course meal at restaurants like Arepas Steakhouse, Bizou, Maru, Bang!, and so many more! Find a full list of participating restaurants here.

Want to take a few days to enjoy all the options? Book a room at one of our boutique hotels whose restaurants are taking part in Charlottesville Restaurant Week. A world-class meal, just steps from your room! There's 1799 at The Clifton, The Ridley located at The Draftsman Hotel, or The Lobby Bar + Restaurant, housed inside The Doyle Hotel.

7) Go to Poetry Night at a Whiskey Bar

If you're looking for a fun night out, look no further than the Doyle Hotel's Speakeasy Whiskey Bar. Every first Friday of the month from 8-10PM (January 3rd), Charlottesville Poem Store founder, Laura Frantz, will be on-site to write a custom poem for each guest on her vintage typewriter. Then, head to the bar and order a cocktail from master mixologist Joel Cuellar who will use your poem to create a bespoke cocktail tailored to your unique preferences.

8) Enjoy a Wood-Fired Sauna Experience

Take in an authentic, wood-fired sauna experience at the Rivanna River Company' Riversong Saunas -- complete with a cold plunge into the Rivanna River! Both of their saunas are made with Atlantic White Cedar paneling & heated with a Kuuma wood-burning sauna stove. No experience is necessary to enjoy this practice that spans cultures and thousands of years and boasts many physical and mental health benefits! Book a private session or mingle during a community session (mixed-gender and women-only available).

Arrive early or stay after your session to enjoy the new tea room, where you can relax with a hot cup of tea or delicious charcuterie board and take in the beauty of the riverfront location. Afterwards, head to Högwaller Brewing for a pint and a bite to eat or to Sugarbear Ice Cream for some decadent (and classic) ice cream flavors. The small shop has also partnered with local downtown staple Revolutionary Soup to serve up soup options every Saturday and Sunday from 10AM - 8PM. Updates to their rotating menu can be found on their Instagram page!

9) Enjoy MLK Weekend Events

10) Go on a Sunrise/Sunset Hot Air Balloon Flight

Nothing says adventure like riding in a hot air balloon over Albemarle County! Take in breathtaking views with Monticello Country Ballooning or Blue Ridge Ballooning -- both providers operate year-round and offer a number of experiences including private flights! Check out their sites for more specific details, like packages, requirements, and rates!

Credit: Photo Credit: Sanjay Suchak

11) Go on a Private Horseback Trail Ride

Have you ever ridden a horse through a vineyard? With Indian Summer Guide Services, you could on your next trip to Charlottesville! This family-owned and operated business offers unique horseback riding experiences to visitors -- a fun, safe and relaxed ride for all skill levels. Trips are available year-round and include trails on some of the area's finest wineries, farms, breweries, and cideries! Check out their website for more details on packages, pricing, and to book your own experience!

Book Your Stay

January is one of the most affordable times to visit Charlottesville and Albemarle County – so book your stay today! Choose from a winery getaway, boutique stay, family friendly hotel, and more.

Looking for more ideas of what to do during your trip? Check out our Ultimate Winter Bucket list for inspiration!