Winter Wine Weekend 5

February 27 - 28

Several Wine Glasses Are Filled With Red Wine
Get ready for a weekend of pure indulgence and discovery at Hotel Madison’s 6th Annual Winter Wine Weekend, happening February 27–28, 2026! This beloved signature event brings together friends, family, wine lovers, and passionate winemakers for a celebration of flavor, learning, and connection.

Picture yourself sipping from 16 world-class Virginia wineries during the Grand Tasting, engaging in a laid-back Winemaker’s Panel, and ending your evening with a four-course wine-paired dinner crafted by Chef Tassie Pippert.

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A Person Smiling At A Table With Wine Glasses

ROOM PACKAGES

SAVE 20% NOW

For a limited time, snag a room package starting at just $222 per night — Grand Tasting included! Sip, stay, and savor the whole weekend. Package includes a two-night stay (Friday and Saturday night) in our well-appointed guestrooms with admission ticket(s) to the Grand Tasting event on Saturday, February 28th, 2025. As part of booking this exclusive offer, you will also receive two (2) complimentary admission tickets to Friday's Winemaker Panel.

Single Attendee

Double Attendee

A Couple Of Wine Glasses On A Table

THE GRAND TASTING

16 AWARD-WINNING WINERIES

The highlight of Hotel Madison’s Winter Wine Weekend is undoubtedly the Grand Tasting — a lively, indulgent Saturday event that brings together 16 of Virginia’s most celebrated wineries. Guests enjoy a generous pour of locally crafted vintages while strolling through beautifully adorned tasting stations, each offering a unique glimpse into the region’s terroir. Attendees are given a keepsake Riedel glass and a wine passport, making it easy and fun to track each tasting and revisit favorites. With live music setting the mood, wine-related vendors, and gourmet bites to pair, the Grand Tasting is as much a social celebration as it is a sensory journey — perfect for both seasoned connoisseurs and curious newcomers.

TICKETS ON SALE DECEMBER 1ST