Virginia wine country comes alive during the holiday season with a festive blend of wine, culture, and celebration. The region’s picturesque vineyards and wineries offer an array of events, from cozy wine tastings by roaring fireplaces to grand holiday markets filled with artisanal crafts and seasonal delicacies. Visitors can sip mulled wine, enjoy live music, or participate in wreath-making workshops at wineries scattered across the Blue Ridge Mountains and rolling countryside. Many wineries also host elegant holiday dinners, pairing seasonal dishes with their finest vintages. Illuminated vineyards and tasting rooms decked in twinkling lights add to the magical atmosphere, making Virginia wine country a must-visit destination during the holidays.
Family-friendly festivities are abundant, too, with activities like carriage rides through scenic vineyards and visits from Santa Claus. Couples and groups often enjoy guided wine tours, where they can sample award-winning blends while soaking in the wintery charm of the region. Special wine releases and discounts on bottles make it a great time to stock up for holiday parties or gifts. Whether you’re a seasoned wine enthusiast or just looking for a unique way to celebrate the season, Virginia wine country offers a perfect blend of relaxation and holiday cheer.
Wine Dinners & Tastings
Bluestone Vineyards Winemaker’s Dinner
(Bridgewater, VA)
The annual Christmas Winemaker’s Dinner at Bluestone Vineyard is a festive celebration of fine wine and gourmet cuisine. Guests enjoy a multi-course meal by North Ridge Café specially curated to pair with Bluestone’s award-winning wines, creating a memorable culinary experience. Attendees also have the opportunity to meet the winemaker and learn about the vineyard’s production process.
Saturday, December 14th at 7:00 PM
Barboursville Vineyards’ Christmas Celebration Lunch
(Barboursville, VA)
The annual Christmas Celebration Lunch at Barboursville Vineyards is a cherished holiday tradition. Held in the elegant Palladio Restaurant, the event features a festive multi-course menu prepared by Executive Chef Michael Clough and expertly paired with Barboursville’s finest wines. The experience highlights the culinary artistry of the chefs and the excellence of Barboursville’s wine craftsmanship.
Sunday, December 22nd
Light Shows & Vineyard Walks
Bluemont Vineyard Lighting of the Vines Winter Holiday Dinner
(Bluemont, VA)
Join Bluemont Vineyard for an unforgettable evening of delectable wines, seasonal flavors and festive holiday cheer. Ascend the mountain for a magical holiday experience in the heart of Virginia Wine Country. Step into the enchanting ambiance of The Stable, beautifully adorned with twinkling holiday lights and elegant decorations. This cozy and festive atmosphere is the perfect setting for a holiday celebration infused with elevated country-chic charm.
Weekly on Saturdays, December 7th – 28th at 5:30 PM
Castle Glen Winery
(Doswell, VA)
Enjoy the Illuminate Light Show from the comfort of your vehicle. Drive through the park and be amazed by nearly a million LED lights synchronized to festive music broadcasted through your car radio. Visit Sunday through Thursday for a less crowded experience. The Light Show is open every day, including in rain and snow. In case of severe weather, check our Facebook, Instagram, and Twitter for closure updates.
November 15th – December 31st from 5:30 to 10:00 PM
Veritas Illuminated
(Afton, VA)
Back for a third season, Veritas Vineyards & Winery has reassembled the Veritas Illuminated Light Show, a dazzling walking light trail winding through the grove and vines of the vineyard. Enjoy Veritas after the stars come out and the lights come on! Warm up near the fire with a cup of mulled wine, or gather with friends around your favorite bottle of Veritas wine. Fun for the whole family, the accessible trail is excellent for families with small children, those wanting to bring their dogs and couples looking for a magical date night.
November 22nd – January 24th, Fridays – Sundays from 5:30 to 9:00 PM
Meet & Greets and Photos with Santa
Cana Crafts & Cheer
(Middleburg, VA)
Visit Cana Vineyards & Winery of Middleburg for a full day of celebration and good cheer featuring their famous mulled wine, talented local artisans, s’mores by the fire pits & more. For an extra special treat, Santa Clause will make his way to the tasting room from 2 pm to 4 pm for photo opportunities.
Sunday, December 08 at 12:00 PM
Cunningham Creek Winery
(Palmyra, VA)
Visit Cunningham Creek Winery for the chance to have festive holiday photos taken of your pets! This is the perfect opportunity to get this year’s holiday photo card. Get a great picture of your dog solo or with the family. All photos provided digitally. There is no fee, but a $20 donation (cash or check) is requested for Brother Wolf Animal Rescue in Asheville, NC whose entire facility was destroyed by Hurricane Helene.
Saturday, December 7th at 10:00 – 11:30 AM
Hillsborough Vineyard & Winery
(Hillsboro, VA)
Santa is back and ready to hear about holiday wishes and pose for pictures with you & yours! Grab your cameras and take a photo of your children visiting with Santa. Enjoy treats & activities for the kids and wine & beer for adults. Proceeds benefit Toys & Tots charity.
Saturday, December 7th at 12:00 PM
Gray Ghost Vineyards
(Amissville, VA)
Children of all ages are invited to bring their wish lists and visit Santa Claus. Attendance includes a free gift for each child, plus a photo with Santa. Cousins Maine Lobster food truck will be on-site from 11:00 am to 5:00 pm. Enjoy lunch and a visit to Santa! Make a day of it!
Sunday, December 15th from 1:00- 4:00 PM
CrossKeys Vineyards Illumination Party
(Mt Crawford, VA)
It’s that time of year again! Head to CrossKeys Vineyards for their Annual Holiday Illumination. Reservations are only required if you plan to dine in the Bistro, while live music by the tree will be provided by Jimmy O. accompanied by Hot Chocolate and a Cookie Station. They will also have a guest appearance from their very own Santa Claus!
Friday, December 06 from 5:00 to 8:00 PM
Eastwood Farm & Vineyard
(Charlottesville, VA)
Join Eastwood Farm & Vineyard for a special visit from Santa, plus holiday milk and cookies flights available again by popular demand. This is a no-cost indoor event with opportunities to take your own photos with Santa.
Weekly on Sunday from December 8th – 22nd
Local Parades
Middleburg Christmas Parade
(Middleburg, VA)
On the first Saturday in December the Christmas Parade begins just after lunch, featuring foot beagle hunt clubs, polo clubs, animal affinity groups, community groups, enthusiasts, business floats, reenactment bands and high school bands, with Santa on his coach drawn by matched Ayrshires closing the parade.
Saturday, December 7th at 2:00 PM
Fine Arts & Theater Presentations
Veritas Waynesboro Choral Society
(Afton, VA)
Back for the third year in a row, Veritas is excited to welcome back the Waynesboro Choral Society as they serenade us with all of your favorite holiday hymns and songs. Entry into the Tasting Room to enjoy the singing is free, tickets for Veritas Illuminated are required for entry.
Friday, December 20th at 6:00 PM
The American Shakespeare Center
(Staunton, VA)
The ultimate tale of transformation, Charles Dickens’ A Christmas Carol transports miserly Ebenezer Scrooge high above the streets of Victorian London, where Ghosts of Christmas Past, Present and Future haunt his dreams…accomplishing, in one fateful night, what a lifetime of grasping and greed could not do: the warming of his cold, cold heart. Join a holiday tradition beloved by families and friends of all ages!
December 5th -29th
Holiday Carols at Eastwood
(Charlottesville, VA)
Enjoy live music, award-winning wines, and $5 tapped beer & cider at Eastwood every Thursday. Gather your friends and family and join us for your favorite beverage, live music, and delicious food. Join Eastwood on December 19th for a special Holiday Carol edition of this exciting event.
Thursday, December 19th at 5:00 PM
Christmas Shopping Markets & Bazaars
Bluestone Vineyards German Market
(Bridgewater, VA)
Bluestone’s 14th Annual Weihnachtsmarkt in December will be held outside on the grounds of the vineyard. Weihnachtsmarkt are traditionally held in Germany, known for their food, drinks and seasonal hand-crafted items. Bluestone’s market will highlight local crafts and artisans. Food trucks, local vendors, and Gluhwein will all be there to help you get into the holiday spirit! Bluestone is also hosting a canned food drive that began in the end of November and will continue through the holiday season. Please bring a canned good on December 7th to support the Blue Ridge Area Food Bank!
Saturday, December 7th from 11:00 to 5:00 PM
Bluemont Vineyard German Market
(Bluemont, VA)
Bluemont Vineyard’s German Holiday Market is a festive event held annually at the vineyard, showcasing German-inspired holiday traditions. Guests can browse through artisan vendors offering handcrafted gifts, ornaments, and specialty holiday goods. Traditional German fare, such as bratwurst, pretzels, and mulled wine, adds to the authentic festive atmosphere. Live music and holiday decorations enhance the cheerful spirit, making it a perfect outing for families and friends. Nestled in the scenic Virginia countryside, the market provides a unique opportunity to celebrate the season while enjoying breathtaking views and award-winning wines.
Saturday, December 7th – December 21st
Eastwood Holiday Market
(Charlottesville, VA)
Join Eastwood Farm & Winery at their Christmas Market! Expect holiday cheer, unique shopping opportunities and delicious food & drinks. Bring your family and friends for a day filled with fun, food, and festive vibes!
Saturday, December 14th from 12:00 – 5:00 PM
Workshops & Classes
Gingerbread Days at The Market at Grelen
(Somerset, VA)
Join The Market at Grelen for a cozy gingerbread house-making evening! Indulge in a cozy holiday atmosphere as you channel your inner child and decorate a gingerbread house, complete with a selection of festive candies and natural elements. Sip on wine and enjoy their enchanting setting, creating lasting memories. Then, join them at Grelen’s Gingerbread Design Studio for a festive workshop where kids (ages 6-12) can create their own gingerbread house masterpieces! It’s the perfect holiday outing for parents, grandparents and little ones alike.
Wine Night: Thursday, December 12th
Workshop: Saturday, December 14th
The Market at Grelen Holiday Wreath Workshop
(Somerset, VA)
Get festive and creative with the Market at Grelen’s popular wreath-making workshop. Create a beautiful holiday wreath using fresh cuttings from their nursery fields. Perfect for all skill levels.
Sunday, December 8th
Christmas Trees & Displays
Gray Ghost Christmas Cork Display
(Amissville, VA)
See the world’s largest cork Christmas display containing over 300,000 corks crafted by owner and winemaker, Al Kellert. Over different 25 works of art are on display for your viewing pleasure. See the winery hours page to plan your visit. Plan a visit before the New Year arrives!
Open through December 31st
Open Houses, Parties & Festive Fun
Southwest Mountains Vineyards Après Ski Open House
(Keswick, VA)
The theme of après ski, the ticket will include food and live entertainment provided by Cake Fight! Take an extra moment to pose for a photo opportunity beside their fabulous 15-foot Christmas tree.
Friday, December 13th at 6:00 PM
Flying Fox Christmas Vacation 2
(Afton, VA)
Back for the holiday season for the second year in a row, Flying Fox Winery & Vineyard’s “Christmas Vacation 2” are bringing back some of your favorite cocktails from last year and introducing a couple of exciting new additions. The Flying Fox Tasting Room is dog-friendly, and pups must remain on a leash at all times to respect other visiting patrons. In addition to the festive and movie-themed cocktails and mocktails, wine will be available for purchase by the bottle and the glass. Outside food is allowed in the Tasting Room, and the only food item sold will be the Little Debbie Christmas Tree Cakes.
Fridays and Saturdays between November 29th and December 21st at 5:30 PM
Historic Holiday Events
Holiday celebrations in Virginia’s historic towns offer a charming blend of tradition, community spirit, and festive ambiance. Towns like Williamsburg, Alexandria, and Middleburg come alive with twinkling lights, decorated storefronts, and seasonal events that showcase their rich history and unique character. Visitors can enjoy colonial reenactments, candlelit tours, horse-drawn carriage rides, and lively Christmas parades. Local markets and artisan fairs provide opportunities to shop for handcrafted gifts while savoring holiday treats and warm beverages. These towns create a nostalgic and magical atmosphere, making them ideal destinations for embracing the holiday spirit.
New Year’s Eve
Veritas New Years’ Eve Masquerade Ball
(Afton, VA)
Ring in 2025 at Veritas with a decadent five-course wine-paired dinner, dancing, and celebration! Gather your friends, masquerade masks, black tie attire, and dancing shoes for a memorable way to welcome the New Year. After the midnight toast, enjoy a hearty breakfast buffet to close out the festivities.
Thursday, December 31st at 7:00 PM
Barboursville Vineyards’ New Years’ Eve Celebration
(Barboursville, VA)
Barboursville Vineyards’ New Year’s Eve celebration is a sophisticated event marking the start of the new year with elegance and style. Held in the Palladio Restaurant, the evening features an exquisite five-course dinner prepared by Executive Chef Michael Clough and paired with the vineyard’s premium wines. Guests enjoy a warm and inviting atmosphere, complete with festive décor and impeccable service. The celebration includes a midnight toast with sparkling wine.
Thursday, December 31st
