Special Events

Thanksgiving

Thursday, November 28 | 1:00 PM and 3:30 PM

Celebrate Thanksgiving with wine, delicious food, and comfort at The Williamsburg Winery! Gather with family and friends in Wessex Hall as we share a Thanksgiving meal specially curated by Chef Shane Henderson. Our buffet will be full of traditional favorites and home-cooked touches alongside paired Williamsburg Winery wines and seasonal cocktails. 

2 seating times are available at 1:00 pm and 3:30 pm. Your reservation includes access to the buffet for one person and a welcome drink upon arrival. Wine and cocktails will be available for purchase. Children pricing (12 and under) is available to reserve. Children 3 and under are free.

Make a weekend of it! Wedmore Place, the winery’s on-site inn, is available for your comfort. Book a room for the family or with friends and enjoy our Wessex Hundred farm for the holiday weekend. https://williamsburgwinery.com/stay/

A Taste of Italy: Meet the Winemaker and Wine Pairing with Sassaia

Thursday, December 12 | 6:00 PM

Experience Italy in a glass at our Meet the Winemaker event with Sassaia Wine! Join us for an unforgettable evening as we bring the flavors of Italy to life and offer an exclusive chance to meet our good friends from Sassaia. Sample an exquisite selection of their Italian wines and enjoy perfectly paired hors d’oeuvres crafted by our own Executive Chef, Riccardo Rinaldi. Mingle with the winemaking duo, Ellen and Enrico de Alessandrini from Sassaia, alongside Williamsburg Winery CEO, Michael Weatherly and Cierra Weatherly. Discover the amazing stories behind their partnership, gain knowledge on each bottle of wine, and learn about the art of Italian winemaking.

Plus, we will have glasses and bottles of your favorite Sassaia wines available for purchase to enjoy during the event or take home and savor for later. Don’t miss this chance to taste, learn, and experience Italian wine in a whole new way. Reserve your spot today!

Wine Tasting Lineup:

Gigi Spumante Brut - Paired with Tuscan Prosciutto Crudo & Dates

Jacqueline Brut - Paired with Cured King Salmon, Mascarpone & Dill 

Derthona - Paired with Caprese Stuffed Vine Ripened Cherry Tomato

Piemonte Chardonnay - Paired with Crostini, Fresh Ricotta & Olives 

Piemonte Dolcetto - Paired with Parsnip Soup, Black Garlic, Vanilla

Monferrato Rosso - Paired with Sausage and Balsamic Reduction

Monferrato Rosso “San Gio” - Paired with Polenta Bites, Taleggio Cream, Winter Black Truffle

Tickets are $30 (plus tax) and include a tasting of all 7 wines and paired bites. Additional wines by the glass and bottle will be available for purchase. Must be 21+. Cancellation Policy: No refunds will be issued 7 days before the event.

New Year's Eve Dinner

Tuesday, December 31

Ring in the New Year at The Williamsburg Winery! Celebrate in style with a decadent New Year’s Eve Dinner at The Gabriel Archer Tavern, crafted by our Executive Chef, Riccardo Rinaldi and our Events Chef, Shane Henderson. Enjoy a gourmet 5-course meal, each dish designed to delight and inspire your senses. For the ultimate dining experience, enhance your evening with our optional wine pairings, each selected to perfectly complement every course.

Pricing and Reservations: Our New Year’s Eve Dinner is $100++ per person and $95++ for Wine Club Members*. Plus, add on wine pairings for an additional $30. Reservations can be made through The Gabriel Archer Tavern’s Opentable link on our website or by calling the host stand at 757-564-8869. Choose any available reservation time and party size from 5:00 - 8:00 PM. Tables are limited, reserve today for an unforgettable night of fine dining, exceptional wines, and New Year’s magic!

Make a night of it! Our European-inspired inn is also available for overnight accommodations. Book a room at Wedmore Place for a relaxing retreat only steps away after dinner. https://williamsburgwinery.com/stay

Need after dinner plans? Continue the celebration with our exclusive party next door at Wedmore Place’s Wiley Bar! Hotel guests and dinner attendees are invited to enjoy wine, beer, and a festive gathering as we watch the ball drop together.

*Taxes and Gratuity are not included. Payment will be taken at the end of dinner. Our New Year’s Eve 5-Course Menu will be the only menu available.

Wine & Brine Series

Every Friday, 4:00 - 8:00 PM

September 13 - November 22

Kick off your weekend with the perfect pairing at our Wine & Brine series! Every Friday, indulge in the freshest oysters, finest wines, and live music at our Outdoor Pavilion. Dive into a selection of succulent oysters provided by Big Island Aquaculture, expertly paired with a curated range of your favorite Williamsburg Winery wines that will elevate your tasting experience. It’s more than a Friday Night Out — it’s a celebration of Coastal Virginia flavor!

📅  Every Friday, 4:00 - 8:00 PM

📍  Gabriel Archer Outdoor Pavilion

🦪  Available by the Half Dozen or Full Dozen

🎵  Local Live Music

No reservations required, seating is first come. Event is weather dependent.

*Outdoor Pavilion to-go menu will not be available during Wine & Brine. For Dinner or additional food, please make a reservation at the Gabriel Archer Tavern.*

Live Music Weekends

Select Fridays and Every Saturday & Sunday

Meet us at our Gabriel Archer Outdoor Pavilion and enjoy live music by local artists plus wine, food, cocktails, vineyard views, and more! View the full lineup for live music dates on our Facebook Page under Events.