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.


Valentine's Day Dinner
February 13-15, 5:00 - 8:00 PM
Valentine's Day Dinner
February 13-15, 5:00 - 8:00 PM

Indulge in a romantic evening at Gabriel Archer Tavern for Valentine’s Day Weekend. Savor an exquisite 4-course meal crafted to perfection by our Executive Chef Riccardo Rinaldi, with the option to elevate your experience by adding wine pairings. The enchanting ambiance awaits you, making it the perfect setting for a memorable celebration of love. 


Reservations are available February 13 - February 15 from 5-8 PM. Book your table by visiting the Gabriel Archer Tavern on Opentable or by calling the host stand at (757) 564-8869. Dinner is $85++ per person, $80++ per wine club member. Wine pairings are an additional $30.


*Pre Fixe Valentine’s Menu only. Regular dinner menu is not available. Reservations are required. Payment will be taken at the end of your dinner. Price does not include taxes and gratuity. 


Continue the celebration and escape to romance! Wedmore Place, our charming European-inspired inn, offers the ideal cozy retreat for a romantic weekend away. Choose from 28 enchanting rooms or elevate your stay with one of our special packages. The Romance Package or the Virginia is for Wine Lovers Package features thoughtfully curated experiences designed to spark connection and create unforgettable memories.


Book a Reservation


View Valentine's Dinner Menu


Valentine's Prom
February 15, 7:00 PM
Valentine's Prom
February 15, 7:00 PM

Get ready to relive the magic of prom—this time with a grown-up twist! Join us on Saturday, February 15, for a night filled with nostalgia, romance, and retro vibes at our Valentine’s Adult Prom.


Dance the night away to the ultimate throwback beats spun by a live DJ, featuring all your favorite hits from the 80s and 90s. Dress to impress in your best 80s and 90s-inspired outfits—think neon, ruffles, sequins, or classic prom tuxes. Light snacks and desserts included to keep you fueled for the dance floor. Prom Punch, Wine, & Drinks will be available for purchase to keep the party going.


Grab your partner, your squad, or fly solo—this is one Valentine’s celebration you don’t want to miss. Don’t wait; tickets are just $35+ and going fast!


No need to rush home for curfew! Wedmore Place, our charming European-inspired inn, is just steps away and offers the perfect place to rest your head after a night of partying. www.williamsburgwinery.com/stay


PURCHASE TICKETS


*Guests must be 21 or older to attend. Cancellation Policy: No refunds will be issued 7 days before the event.


Sourdough Class: Intermediate
February 16, 4:00 PM
Sourdough Class: Intermediate
February 16, 4:00 PM

Hosted by Virginia Bread Company


Already know the basics of sourdough and looking to expand your repertoire? This all inclusive experience will cover making and preparing fresh sourdough croissants, as well as sourdough discard recipes including delicious crackers and more! At the end of the class we will all enjoy what we’ve made. Bring an apron and a friend, and get ready to bake!!!


This class will be held at the Williamsburg Winery. All ages are welcome! The restaurant is open for dining, and drinks are available to order as well if you’re interested in a sip & bake experience.


We will be getting messy… bring an apron if you’d like! Not necessary but good to have: your own rolling pin and cutting board (so you don’t have to share). You will also have the dough you made in class to take home and bake yourself!


Purchase Tickets Here

Pasta & Vino: A Winemaker Dinner Experience
February 24, 5:00 - 8:00 PM
Pasta & Vino: A Winemaker Dinner Experience
February 24, 5:00 - 8:00 PM

Join us for a night of culinary excellence at Pasta & Vino, a special Winemaker Dinner featuring Chef Riccardo Rinaldi and our friends from Sassaia Wines in Italy. On Monday, February 24, from 5:00 to 8:00 pm, elevate your usual Monday Pasta Night with a carefully curated three-course Italian meal, each paired perfectly with a Sassaia wine selection.


Chef Riccardo will take you on a journey through the authentic flavors of Italy, while Enrico and Ellen de Alessandrini, the passionate winemakers behind Sassaia, share their stories and expertise.


This unforgettable evening is just $80++ per person, $75++ per wine club member. Reservations are highly recommended. Secure your spot now on OpenTable or by calling the host stand at 757-564-8869. Don’t miss this unique celebration of Italian cuisine and wine!


VIEW MENU


MAKE A RESERVATION


*The Pasta & Vino 3-Course Menu will be the exclusive offering for the evening. Our regular dinner menu and traditional Pasta Night menu will not be available. Payment will be collected at the conclusion of your dinner service, and please note that the price does not include taxes or gratuity.


Vineyard Fun Run
March 8, 9:00 - 11:00 AM
Vineyard Fun Run
March 8, 9:00 - 11:00 AM

Lace up your running shoes and get ready for a scenic and spirited adventure at the Williamsburg Winery’s Vineyard Fun Run on Saturday, March 8, from 9 - 11 AM! This unique 3-mile run will take you through the rolling vineyards and around the beautiful Wessex Hundred farm, with three tasting stations along the way—sip red, white, or rosé (or grab some water) as you go! 


REGISTER TODAY HERE!


Each participant will receive one drink ticket to use on wine or non-alcoholic beverages. After the run, stick around for good vibes with tunes, warm spiced wine, and hearty homemade chowder available for purchase. Plus, the Tasting Room will be open for wine and Gabriel Archer Tavern will be serving lunch starting at 11am.


The top three finishers will score exciting prizes, and all participants will have the chance to enter to win incredible raffle items, including weekend stays, free wine tastings, and gift cards. A portion of the proceeds will benefit Vet First Inc., supporting our veterans and the local food bank. Registration is just $30, so grab your friends and family and join us for an unforgettable day of fitness, wine, and fun in the vineyards! Children are welcome. Registration begins at 9am, Race begins at 10am.


Vet First is a non-profit that provides employment to local Veterans and ties together agriculture with giving back to the community. Vet First is near and dear to us at Williamsburg Winery as we currently have our farm location on site at the winery where crops and produce are maintained by Veterans and donated to the local community. 



Chef's Notebook
March 12, 6:00 PM
Chef's Notebook
March 12, 6:00 PM

Experience a night of culinary artistry and connection at our Chef’s Notebook Series, reintroduced with our renowned Executive Chef, Riccardo Rinaldi. On Wednesday, March 12, at 6:00 PM, treat yourself to an exclusive evening that promises:


  • A Unique Opportunity to Connect with Chef Riccardo Rinaldi as he shares his inspirations and techniques behind each dish
  • An Intimate 3-Course Dinner thoughtfully paired with exquisite wines from our collection
  • A Cozy Setting perfect for meaningful conversations and a truly memorable dining experience

MAKE A RESERVATION, MARCH 12

VIEW MENU


Whether you're a foodie, a wine lover, or just looking for a unique dining experience, this evening is not to be missed! Seating is limited—reserve your spot today! Book your reservation through Opentable or by calling the host stand at (757) 564-8869. Dinner is $80++ per person, $75++ per wine club member, and includes all courses and wine pairings.


*Reservations are required. Payment will be taken at the end of your dinner. Price does not include taxes and gratuity. 


Wine & Art Exhibition
March 22, 12:00 - 5:00 PM
Wine & Art Exhibition
March 22, 12:00 - 5:00 PM

Join us for an afternoon of wine and creativity at our Wine & Art Exhibition on Saturday, March 22, from 12–5 PM in Wessex Hall! This free event invites you to sip on your favorite Williamsburg Winery wines while exploring a stunning showcase of local artistry. Browse and shop a diverse collection of works, including acrylic and oil paintings, metalwork, watercolors, and more—all available for purchase. Whether you're an art enthusiast, a wine lover, or simply looking for a unique way to spend the day, this event is the perfect blend of culture and craftsmanship. Don’t miss it!


Featured Artists:

Kay Krapfl

Laurie Rokutani

Hellen Bennett - Watercolors

Tom Zuk

Lilyann Teifer

Barbara Oakes

Amy Argo

Sharon Parker

Marc Chabrier - Modern Contemporary, Abstract, Acrylic Pour Painting

Ellen Biesack - Watercolors

Monica Schauffler

Kelly Mazzrillo - Art Ore Decor

Bren Douros

Edee Lyons

Anne Brooks

Dolly Georgieva-Gode

Judy Leasure

Bob Carlson

Janet Price - Watercolor Miniatures

Linda Dessaint

Lucinda Miller

Bill White

Linda Landreth Phelps

Annette Thompson - 2D Encaustic & Cold Wax Work

Cellar Dinner Series, WINE CLUB EXCLUSIVE
March 26 & 27, 6:30 PM
Cellar Dinner Series, WINE CLUB EXCLUSIVE
March 26 & 27, 6:30 PM

Open to Wine Club Members only. Join Winemaker Stacey Lightfoot and Events Chef Shane Henderson for an unforgettable evening in our wine cellar and barrel room, where exclusivity meets elegance. This special event is open to Wine Club Members only and available for two nights with limited capacity! Your night begins with a refreshing welcome splash of sparkling wine, setting the tone for a truly unique experience. Winemaker Stacey Lightfoot and team will guide you through a private cellar tour, sharing fascinating insights into our winemaking process and the stories behind our wines. Afterward, take a seat in our intimate barrel room and indulge in a carefully curated 3-course dinner crafted by our talented Events Chef, Shane Henderson, perfectly paired with our wines.


RESERVE TICKETS

VIEW MENU


Tickets are $80+ per person, and seating is limited for this intimate gathering. Reserve your place today and savor a night of fine dining, exceptional wines, and memorable moments in a setting like no other. 


If you missed this incredible dinner, don’t worry—there’s more to come! Stay tuned for our next Cellar Series with Chef Shane and Stacey this Spring and Summer.


*Open to Wine Club Members Only. Limited to two tickets per reservation. Guests must be 21 or older to attend. Cancellation Policy: No refunds will be issued 7 days before the event.


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

3 COURSE ONLY $45!


Experience a rotating weekly menu showcasing a unique pasta dish expertly crafted by our Executive Chef, Riccardo Rinaldi. Each meal is served with a fresh salad and dessert, with optional wine pairings available for purchase.


5-8 PM - Reservations Encouraged through Opentable. 


*Only Pasta Night Meny 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. 


*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.

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