Special Events
On every one of our corks is printed ‘Enjoy Life’ which is a reflection to how we should live.
Join us for one of our special events and enjoy life with delicious wine in the company of great friends here at Wessex Hundred.


Every Sunday, come to the Williamsburg Winery and play Speedquizzing Trivia, hosted by Matt Chambers and Matt Mullins of Speedquizzing VA.
We will be alternating hosting on Sundays.
This is going to a brunch event, with wine, food, beer, and other non-alcoholic options. The fun begins at 2:00 PM in The Tasting Room. Trivia Rounds to include General Knowledge, Music, and Specialty Themed Rounds, and the top 3 teams will win a Williamsburg Winery gift cards! First Place will be crowned the Speedquizzing Trivia Champion!


Join us for an elegant evening as we unveil Jefferson’s Journey, Williamsburg Winery’s newest wine collection and our first collaborative release with our sister winery, Sassaia, located in the heart of Piemonte, Italy.
Curated by Williamsburg Winery CEO Michael Weatherly and Sassaia CEO Enrico Alessandrini during Michael’s recent visits to Piemonte, this collection celebrates the shared passion and craftsmanship between our two wineries.
Your evening includes a guided tasting of four exceptional wines, each thoughtfully paired with Mediterranean-inspired small bites—a homage to Jefferson’s “Grand Tour” through Italy.
A known wine enthusiast, Jefferson spent three weeks exploring Italy, immersing himself in its viticulture, architecture, and engineering. His journey helped shape the future of American winemaking. Now, we invite you to take a similar journey—through taste, story, and culture.
Between courses, enjoy stories and insights from Enrico and Michael, as they share the origins of this collaboration and Jefferson’s enduring influence on their vision.
Jefferson’s Journey: 4 New Williamsburg Winery / Sassaia Wines with Mediterranean Pairings
Journey Station #1
Passeggiata — Spumante Metodo Classico (White Sparkling)
Paired with Anchovy Crostini & Pickled Red Onion
Journey Station #2
Il Segreto — Piemonte Bianco (White)
Paired with Swordfish Crudo, Scallion & Hazelnut, Meyer Lemon Dressing, Pink Peppercorn
Journey Station #3
Pendulum — Piemonte Dolcetto (Red)
Paired with Pacchero Pasta, Duck Leg, Mascarpone-Foie Sauce
Journey Station #4
Piacere — Monferrato Nebbiolo (Red)
Paired with Saffron Taleggio Arancini
Be among the first to experience this transatlantic wine debut and raise a glass to a journey nearly 250 years in the making.




May 16: Lane Rice - 4 PM - 7 PM
May 17: Nate Weiss - 4 PM - 7 PM
May 18: Mercy Creek - 2 pm - 5 pm
May 24: Sammy Lee - 4 PM - 7 PM
May 25: Pancho Villa - 2 pm - 5 pm
May 26: Sam Riddle - 2 pm - 5 pm
May 31: Nathan Lenard - 4 PM - 7 PM
June 1: Glen Lavendar - 4 PM - 7 PM
Come out for an evening at the winery with live music, great food by Chef Ricardo at our award-winning restaurant, fresh oysters, delicious wine and beer, and curated cocktails overlooking the vineyard! Make it a stay and book a room at our European-style hotel, the Wedmore Place. Cheers!


A weekly showcase of tavern classics, featuring the acclaimed Seven Hills Burger and our rotating artisan Pasta, expertly crafted by Executive Chef Riccardo Rinaldi.
5-8 PM - Reservations Encouraged through Opentable.
*Only Pasta & Burger Night Menu Available. Dinner Menu is not available.


Local Residents enjoy 10% off every Thursday!
Calling all Williamsburg and James City County Residents - every Thursday we're offering 10% off during lunch to our favorite locals. Come by and enjoy lunch inside our tavern or on our outdoor patio.
Reservations Encouraged through Opentable.
*Must show an I.D. as proof of residency. Discount applies to food and non-alcoholic beverages. Cannot be combined with other discounts. Applies only to Williamsburg and JCC area zip codes: 23185, 23186, 23187, and 23188.