A Group Of Wine Glasses On A Table

Winter Wine Weekend 2024

A Learning, Tasting and Dining Experience

Makes a wonderful holiday gift, too!

A Painting Of A Person Holding A Glass And A Bottle

IMPORTANT:  To make reservations for rooms packages and to purchase tickets to optional experiences, please scroll down this page to find those booking links (gold buttons).  Thank you!


Winter Wine Weekend has proven to be one of our most popular events and a favorite among the winemakers as well as our guests and community. Connect with family, friends and others at Hotel Madison over this shared interest of wine.

Multiple events will be offered from experiential learning and wine-paired dinners with experts to the Grand Tasting on Saturday with up to 15 participating wineries and a special Sunday brunch. Wine-related vendors will be here, too.  Consider giving a holiday gift of this special experience!

Schedule of Events

WINE-PAIRING DINNER | Friday, February 23rd, 7:00 pm | $110 per person
Winter Wine Southern Style with Matt Carothers



Saturday, February 24th   11 am – 5 pm
Up to 16 wineries * hors d'oeuvres * music * wine-related vendors

Among the participating wineries are:

  • Ankida Ridge
  • Barren Ridge
  • Bluestone
  • Brix and Columns
  • Cardinal Point
  • Cross Keys
  • Eastwood
  • Grace Estates
  • Hark
  • Jake Busching
  • Joy Ting
  • Mountain and Vine
  • The Winery at Kindred Pointe
  • Wolf Gap

WINE-PAIRING DINNER | Saturday, February 24th, 7:00 pm | $110 per person
Hats Off to Virginia Wine with Tassie Pippert



EXPERIENTIAL LEARNING | Saturday, February 24th | $35 per person per session
One-hour long interactive sessions:

10:00 am | Chocolate & Wine-pairing with Tassie Pippert

Learn the art of blending chocolate with wine in this fun, morning class hosted by Tassie Pippert, Certified Specialist of Wine and Certified Chef Emeritus. Explore where tannin and acid of chocolate and wine meet to create an elegant pairing. The class includes chocolates paired with five wines.

11:30 am | Burgundy Wines with Christine Vrooman

More details coming soon!

1:00 pm | Chardonnay with Lee Hartman

Chardonnay is the most popular white wine in the state, the country and world.  Known as the "winemaker's grape", it can change drastically depending on who is making it and where it is grown. Come taste the variety with winemaker Lee Hartman from Bluestone Vineyard as he explores different styles, production techniques and regions from around the world.

2:30 pm | Virginia and Australian Wines with Andrew Bilenkij

More details coming soon!


BUBBLES & BRUNCH | Sunday, February 25th, 9:30 am - 11:30 am | $65 per person
A Sparkling Wine Brunch

With delicious selections and pairings by chefs Tassie Pippert and Matt Carothers, this sparkling wine brunch is a way to conclude Winter Wine Weekend before you head home.  As with our other Winter Wine events, it's also open a-la-carte to locals and our traveling guests who would like to join us just for this event.



Rooms Packages Now Available*

Merry Savings of 15% - for a limited time!


One Night Package Option (save 15%):
$208 single attendee; $271 double attendees

  • 1 night stay either Friday or Saturday night
  • Ticket(s) to the Grand Tasting, valued at $75 per person
  • Private access to purchase tickets to optional wine experiences; limited time

One Night - Single Attendee

One NIght - Double Attendee


Two Night Package Option (save 15%):
$352 single attendee; $416 double attendees

  • 2 night stay Friday & Saturday nights
  • Ticket(s) to the Grand Tasting, valued at $75 per person
  • Private access to purchase tickets to optional wine experiences; limited time

Two Nights - SIngle Attendee

Two Nights - Double Attendee

* PLEASE NOTE: offer valid while availability lasts; prepayment required in full with valid credit card, taxes and any additional room charges are not included; refundable at 50% until January 23, 2024 at which time no refunds will be permitted, no pets permitted during Winter Wine Weekend.


For tickets to these add-on experiences,
please click on the EventBrite button below, click Get Tickets, and then use the special access code included in your reservation confirmation:

Wine-Pairing Dinners | Friday & Saturday
Experiential Learning with Wine Experts | Saturday
Sparkling Wine Brunch | Sunday



Learn more about Winter Wine Weekend from 2023's event: