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.


An Evening Under The Stars
August 30, 2025
An Evening Under The Stars
August 30, 2025

An Evening Under the Stars – Wessex LawnJoin us for a relaxing late-summer evening on the beautiful Wessex Lawn at The Williamsburg Winery. Small bites, our signature cocktail of the evening, plus beer and a selection of wines will be available for purchase.


This is a free event to attend, so bring your friends, unwind, and soak in the charm of the season under the night sky.

Culinary Creations: A Savory Summer Plate Demo
September 4, 2025
Culinary Creations: A Savory Summer Plate Demo
September 4, 2025

Join us for a delightful culinary evening with Executive Chef Riccardo Rinaldi as he brings the flavors of summer to life with a live cooking demo. Watch the magic unfold, learn a few chef secrets, and then savor the delicious meal he prepares. Each ticket includes a complimentary drink!


Cooking Demo On:

Pork Chop with Quinoa Salad



Live Music in the Vineyard
August Lineup
Live Music in the Vineyard
August Lineup

August 2: Nicholas Darden- 4 PM - 7 PM

August 3: Lane Rice - 4 PM - 7 PM 

August 8: 2nd Wind Band- 4 PM - 7 PM

August 9: Pancho Villa - 4 PM - 7 PM 

August 15: Lane Rice - 4 PM - 7 PM

August 16: Sam Riddle - 4 PM - 7 PM

August 22 & 23: Felicia Hoyos - 12 - 3 PM

August 29: Felicia Hoyos - 12 - 3 PM

August 30: Sammy Lee - 4 - 3 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!

Falling Into Fall
September 25,2025
Falling Into Fall
September 25,2025

Thursday, September 25 | 6:00 PM | Dinner at 6:30 PM |


Celebrate the beauty of the season with Falling Into Fall: Dinner in the Vineyard, set among the golden hues of our estate Albariño vineyard. Your evening begins with a sparkling toast upon arrival, followed by a leisurely walk to the vines where a long, table awaits beneath the crisp autumn sky.


As twilight settles over the vineyard, indulge in a thoughtfully curated four-course menu by Chef Shane, each pairing designed to highlight the harmony of food, wine, and the season:


Summer Bacalao

Creamy salt cod • pee wee potatoes • cipollini onions • olives • poached eggPaired with Wessex Hundred Blanc de Blanc


Roasted Quail Gumbo

Semi-boneless quail • dirty rice • sauce à la gumbo

Paired with Virginia Petit Manseng


Intermezzo

Alpine cheese • lotus root • rosé frozen grape elixir


Stuffed Pork Chop

Sweet onion • gorgonzola • apples • pancetta • red wine sauce

Paired with Gabriel Archer Reserve


Meyer Lemon Margarita

Frozen Meyer lemon soup • poached meringue • Grand Marnier gelée • salted lemon madeleine • agave syrup

Paired with Petite Fleur


Between the vines, you’ll enjoy the warmth of good company, the rustle of leaves, and the serene magic that only harvest season can bring.


One of our most beloved traditions, Dinner in the Vineyard, is a celebration of wine, food, and the land that brings them together.


Seating is limited - reserve your place today for an unforgettable night.


No menu substitutions are available.

Thanksgiving At The Williamsburg Winery
November 27, 2025
Thanksgiving At The Williamsburg Winery
November 27, 2025

CANCELLATION POLICY: No refunds will be issued 7 days before the event. Last day to request a refund is November 20th.


* *Choose from 2 seating times - 1:00 PM and 3:30 PM reservations. Regular, Children 12 & Under, and Children Under 3 options available. Please make sure to reserve tickets for all adults and children in your party, including any children under 3 years old, so that we may set our tables and seating charts accordingly.**


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. Wine and cocktails will be available for purchase. Children pricing (12 and under) is available to reserve. Children under 3 are free.


Menu preview to come!


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/

Pasta & Burger Night
Every Monday, 5:00 - 8:00 PM
Pasta & Burger Night
Every Monday, 5:00 - 8:00 PM

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.

Lunch for Locals
Every Thursday, 11:00 AM - 3:00 PM
Lunch for Locals
Every Thursday, 11:00 AM - 3:00 PM

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.

Trivia
Every Sunday at 2 PM
Trivia
Every Sunday at 2 PM

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!