Winter Wine Weekend | 6th annual
February 27 - 28, 2026
Save the Dates!
It's never too early to reserve a weekend on your calendar for indulgence, discovery, and unforgettable moments!
We are delighted to announce the 6th Annual Winter Wine Weekend at Hotel Madison, a signature event that has become a celebrated tradition bringing together friends, family, winemakers and wine enthusiasts for a festive celebration of flavor, learning and community.
As word has spread, Winter Wine Weekend has become the gathering for anyone who loves wine, food and unforgettable experiences. We are excited to share the dates with you now so you can plan ahead.
Room Packages and Tickets will be available soon!
On the Weekend Lineup:
- Grand Tasting with 16 Wineries pouring thoughtful selections
- Winemakers' Panel for insider stories and expertise
- Dessert Reception with Tassie and Wineries (new this year!)
- Wine-Pairing Dinner for an exceptional culinary evening
- Experiential Learning to deepen your appreciation of wine
- Live Music to set the mood and enjoy
- Wine Shop & Vendors to take the experience home
- Sunday Brunch at Monty's for a delicious conclusion
We are excited to have the following 16 Grand Tasting participants:
- Afton Mountain Vineyards
- Ankida Ridge Vineyards
- Barboursville Vineyards
- Bluestone Vineyard
- Brix and Columns Vineyard
- Cana Vineyards
- Cave Ridge Vineyard
- Chatham Vineyards
- Cross Keys Vineyards
- Fifty-Third Vineyard
- Hark Vineyard
- Jake Busching Wines
- Joy Ting Wine
- Muse Vineyards
- Valley Road Vineyards
- Walsh Family Wines
Mark your Calendar now!
Winter Wine Weekend is an event that only grows finer year after year.
SCHEDULE OF EVENTS
WINEMAKERS' PANEL | Friday, February 27, 5:00-6:00 pm | $15 per person
An informal and informational gathering with a wonderful representation of area winemakers.
Join us for an engaging and hour long informal Winemakers’ Panel, where several local wine experts and Shenandoah Cup winners—both past and present—share their stories, insights, and some favorite vintages. Hear firsthand how great wines are crafted, enjoy lively conversation, and discover the passion behind every bottle. Price includes your choice of one of four wines presented to sip along while you learn. It’s an inspiring, down-to-earth event that celebrates the region’s best winemaking talent. Bring your questions!
Ticket(s) to the panel will be included in the rooms package, and will later be available a-la-carte.
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WINE-PAIRING DINNER | Friday, February 27th, 6:30 pm | $125 per person
Chef Tassie Pippert in collaboration with Fritz Underground Winery
A Journey Through the Wine Cave
A Winter Wine Weekend highlight! Indulge in an unforgettable wine-pairing dinner with an incredible 4-course menu by the delightful Tassie Pippert and featuring the wines of California's Fritz Underground Winery. Read more about both in the biography sections on the full menu below and treat yourself to a very special evening.
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GRAND TASTING EVENT | $75 per ticket
Saturday, February 28th 11 am – 5 pm
16 wineries * souvenier Riedel glass & passport * music * wine-related vendors * food offerings & more
Grand Tasting ticket(s) will be included in the rooms package, and available soon as a-la-carte.
Price increases at the door.
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EXPERIENTIAL LEARNING | Saturday, February 28th | $40 per person per session
One-hour long interactive sessions:
10:00 am | Saturday Class | Symphony for the Senses with Tassie Pippert, Certified Specialist of Wine and Certified Chef Emeritus
Learn how your senses work together to bring the flavors of wine to the surface. This interactive class will make you aware of the ways vision, smell, and taste come together to inform what you taste and how that taste can change based on the addition of food.
11:30 am | Say Cheese, Please! with Winebow
Have you ever wondered how to pair wines with just the right cheese? Learn the secrets as you enjoy a selection of cheeses paired with the perfect wines selected by Winebow.
1:00 pm | Wine 101 with Lee Hartman, Bluestone Vineyards & Rootstock Wine Bar
Join ever popular and local Winemaker Lee Hartman as he talks about how wine is made, where it comes from, how to decode a label, and how to pick a good bottle. Learn more about what goes into wine, why Lee travels widely for it, and why wine is considered by many as the greatest beverage in the world.
3:00 pm | Wonderful World of Wine with Jake Busching
Experience a seminar with Jake Busching, owner and winemaker of Jake Busching Wines, as he leads you through his World of Winemaking. Jake is also an instructor at Piedmont Community College in the wine certification program and is a sought-after speaker in the world of Virginia wine. What a treat to have him with lead a seminar this time!
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DINING IN MONTY'S and QUILLS LOBBY BAR
Dinner reservations are encouraged and will open soon; walk-ins welcome and available as space allows during the event weekend.
Keep the day and evening going with an array of dining options and live music in Quills!
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BUBBLES & SWEETS Dessert Gathering | Saturday, February 28th, 8:00 pm – 9:30 pm | $25 per person
With Chef Tassie Pippert and 4+ Participating Wineries
Sip, sparkle, and indulge at our Bubbles & Sweets Reception, an elegant yet relaxed finale to the days' events. Enjoy a delicious array of mini desserts paired perfectly with local sparkling wines and sweet treats, all in a lively, social atmosphere. It’s the ideal way to unwind, mingle, and toast to a great day of flavor—all at a truly reasonable price. Also great for locals looking for an evening sweet treat and Winter Wine Weekend experience.
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BRUNCH IN MONTY'S | Sunday, March 1st, 9:00 am – 2:00 pm
Reservations will open soon and are encouraged.
Finish the weekend with a delicious & nutritious brunch as you head off!
Visit the Monty's website here.