Winter Wine Tour in Charlottesville

Winter is an excellent time to enjoy wine tours around Charlottesville, thanks to cozy tasting rooms, holiday events, and unique seasonal experiences offered by many local wineries. Special holiday fun can include festive decor, fireside tastings, holiday markets, mulled wine, and hands-on activities.

Festive Winery Atmospheres and Events

• Mount Ida Reserve transforms its tasting room into a holiday winter wonderland featuring a 30-foot Christmas tree, a 19th century sleigh, and seasonal warmed port wine cider in December. Their fire pits and enclosed patios make for a cozy winter experience.​
• Grace Estate Winery offers outdoor fire pits, artisan wood-fired pizza, and Friday Raclette Nights in December, where you can try Swiss-style melted cheese with charcuterie.​
• Keswick Vineyards introduces a new, fully enclosed, heated tasting space for winter visits, with guided tastings and flights.​
• Pippin Hill Farm hosts Winter Estate Tastings and has seasonal wood-fired pizza and cooking classes—ideal for holiday date night or small groups.​
• Eastwood Farm & Winery features s’mores around fire pits, hot mulled wine, live music nights, seasonal flatbreads and fondue, and activities for kids like juice flights.​

Holiday-Themed Activities

• Trump Winery’s annual Holiday Market (December 6, 2025) offers a festive shopping experience with local artisans, holiday cheer, and wine tastings amidst vineyard decorations. Horse-drawn carriage rides are sometimes available for a unique touch.​
• Special "Francsgiving" and other seasonal wine-pairing events pair Cabernet Franc flights with holiday bites in a cozy, pre-holiday celebration atmosphere.​
• Many wineries create illuminated vineyard walks, host ornament-making workshops, and offer winemaker holiday dinners, often listed on event calendars for the Monticello Wine Trail and Virginia.org.​

Cozy and Unique Experiences

• Glass House Winery offers tastings inside a tropical greenhouse, perfect for escaping winter’s chill while enjoying wine.​
• Veritas Vineyards and King Family Vineyards feature fireplaces, big couches, and sometimes private or guided tastings within the wine cellar.​
• Merrie Mill Farm is known for its extensive farm-to-table menu, warm ambiance, and group-friendly tastings, making it perfect for holiday gatherings.​
• Lodging at select wineries (e.g., Glass House Winery’s B&B) and holiday-decorated accommodations at Trump Winery’s Albemarle House allow for overnight festive escapes.​

Sample Itinerary Ideas

• Morning at Pippin Hill for a guided tour and cooking class, lunch by the fire with winter wine selections.
• Afternoon s’mores and mulled wine at Eastwood Farm while enjoying live music.
• Evening stroll through Trump Winery’s Holiday Market, wrapping up with a festive dinner at Keswick Hall or a nearby winery restaurant.

Charlottesville’s wine country excels in bringing seasonal joy into its already-acclaimed wine experiences, making it the perfect winter retreat for both locals and visitors looking for holiday magic and warm hospitality.