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.
November 8: Pancho Villa - 4 PM - 7 PM
November 14: Love Cats - 4 PM - 7 PM
November 15: Sam Riddle - 4 PM - 7 PM
November 21: Lane Rice - 4 PM - 7 PM
November 22: Pancho Villa - 4 PM - 7 PM
November 26: Sammy Lee - 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!
Living Succulent Christmas Tree
Join us for the Living Succulent Christmas Tree event at Williamsburg Winery ! Get into the holiday spirit with this unique in-person event. Witness the magic of a Christmas tree made entirely of lush succulents. It's a sight you won't want to miss! The class starts with a hands on guide of how to care for and become an expert on how to make your succulents continue to thrive for many more seasons. You’ll be guided step to step on how to design and create this wonderful living holiday decor. There will be several choices on each step of creating your unique treasure. Sip luscious wines with your group of friends and spend the afternoon at this gorgeous location. Stay after the workshop to spend some time enjoying all the winery has to offer with its many options of dining and in the tasting room.
🎁 Holiday Food Drive at The Williamsburg Winery
We’re proud to partner with Vet First and Grove Christian Outreach to help local families enjoy a warm and joyful holiday meal this season.
Donate non-perishable food items and help spread kindness in our community.
As a thank-you: Receive 10% off wine bottles* when you donate.
Donation Locations:
🍷 Merchants Square Wine Bar
🍷 Wessex Hundred Tasting Room
Suggested Donation Items:
Canned vegetables & fruits
Canned soups or stews
Canned milk
Canned cranberry sauce
Stuffing mix
Boxed mashed potatoes
Rice or pasta
Mac & cheese
Baking mixes (cake, brownie, cornbread)
Broth (chicken, beef, or vegetable)
Pumpkin pie filling
Apple pie filling
Spices
Thank you for helping us support our neighbors this holiday season!
*Discount cannot be combined with points or other discounts. Discount must be used at the time of donation.
✨ November 28–30 | Wessex Hundred✨
FREE EVENT - Not ticketed
Join us for a festive weekend at The Williamsburg Winery as we celebrate the season in true winery style! Sip and shop your way through the estate while enjoying a wine tasting or guided tour, then indulge in a chef-curated lunch or dinner at the Gabriel Archer Tavern.
Cozy up by the fire with a glass of spiced wine or a holiday mimosa, explore our gift shop for unique treasures for the wine lover in your life, and soak in the sounds of cheerful holiday music.
The weekend will be filled with good cheer, warm hospitality, and the joy of gathering with friends and family. It’s the perfect time to savor the flavors of Virginia Wine Country and kick off the holiday season at The Williamsburg Winery.
🍷 Make it a weekend getaway, book your stay at The Wedmore Place and enjoy your own fireplace to keep things toasty and festive. https://williamsburgwinery.com/stay
🎄 Small Biz Saturday & Holiday Tree Lighting | Nov 29
Event at our Merchants Square Wine Bar Location Only!
Support local and celebrate the season at The Williamsburg Winery!
✨ All day: Enjoy 10% off orders for Small Biz Saturday.
🍷 5 PM: Join Merchant Square for the festive Holiday Tree Lighting with a $6 Spiced Wine Soirée, plus in-store crafts and games for all ages.
*Discount cannot be combined with points or other discounts
Step into the charm of a European evening at Café Provençal at Wedmore Place.
Join us for an exclusive four-course wine dinner crafted by the acclaimed Executive Chef Riccardo Rinaldi. Enjoy an intimate night of refined flavors and thoughtfully paired wines from our cellar.
Menu:
Course 1: Cream of mushroom soup, savory and garlic parmesan croutons
Course 2: Halibut, caramelized onion and tomato jam, celery root puree, ember roasted baby carrots, crispy potatoes
Course 3: Risotto saffron and comte cheese, citrus marinated foie gras
Course 4: salted caramel apple pie cobbler
Come early and enjoy Happy Hour at The Wiley Bar open 6-6:30 pm before dinner. This is a CASH bar only.
Join us as we toast to the start of the holiday season with an exclusive evening of wine, history, and flavor.
Grand Illumination Celebration: A Taste of Italy
Tickets: $35 – Includes tastings of four Jefferson’s Journey wines and their paired accompaniments.
Join us as we toast to the start of the holiday season in Colonial Williamsburg and the magic of Grand Illumination with an exclusive evening of wine, history, and flavor.
Embark on A Taste of Italy as you explore Thomas Jefferson’s Journey, a collection of Italian wines inspired by Jefferson’s travels through Italy on a secret trip in 1787. Crafted in collaboration with our Sister Winery Sassaia, this series celebrates Jefferson’s enduring spirit of exploration, culture, and craftsmanship.
Savor thoughtfully paired small bites that complement each wine’s unique story and character, as you’re transported from the rolling hills of Virginia to the vineyards of Northern Italy.
Throughout the evening, enjoy a special meet-and-greet with the owners of Sassaia Winery, as well as The Williamsburg Winery’s CEO and his wife, Cierra, who will be joining in the celebration.
Let this evening be your first toast of the holiday season, a blend of history, hospitality, and the timeless joy of good wine shared among friends.
Join us December 6, 13, & 20 for festive sips and seasonal sparkle! Enjoy $12 holiday mimosas, select sparkling glasses, or $6 hot spiced wine to warm up before the fireworks. Pop open a sparkling bottle, take advantage of Happy Hour on select glasses, and stick around for the 7 PM fireworks!
🪄 Harry Potter Trivia Night | Dec 7, 3–5:30 PM
Step into the wizarding world for an afternoon of spellbinding trivia, good wine, and plenty of friendly competition. Test your knowledge of Hogwarts lore, iconic characters, and magical moments for the chance to win a $50 gift card! Gather your fellow witches and wizards and join the fun.
This workshop will give you many options to fully customize your very own living Winter Wreath. Step by step hands on guidance will be demonstrated by Melissa, the creator and artist behind Rusted Rabbitt. Instructions will be given on how to care for your beautiful living work of art as well.
We will start our class with an extensive succulent tutorial along with creating and designing tips and tricks with living homegrown succulents.
You’ll have so many choices of all the natural materials to use to make yours unique and sometime to admire for many many seasons to come.
******Please note the address for the location. This is not at the main winery location. The workshop is being held at the tasting room location at Merchant Square in Colonial Williamsburg*****
🎤🎄 Ugly Sweater Karaoke & Costume Contest | 3:30–6:30 PM
Break out your most fabulously festive ugly sweater and warm up those vocal cords for a night of holiday karaoke and cheerful competition! Sing your favorites, show off your outrageous outfit, and you could take home a winery gift card. Join us for cozy vibes, good wine, and plenty of laughs!
Start your New Years Eve festivities at the Tavern
Join us for an elegant New Year’s Eve dinner, featuring a thoughtfully crafted menu to celebrate the season! (menu to come)
Elevate your experience by adding our pre-selected wine pairings to your meal +$40.
Make your reservations on OpenTable.
🎉 Ring in the New Year at The Williamsburg Winery | Dec 31 & Jan 1
Celebrate the season with bubbly all day! 🥂 Enjoy $12 mimosas and select sparkling glasses — bottles available at regular price. Plus, enjoy Happy Hour on select glasses and toast to the new year in style!
Holiday Hours: 12 - 6 PM (last call 5:30) both days!
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.
Every Sunday, come to the Williamsburg Winery Wessex Hundred Tasting Room and play Speedquizzing Trivia, hosted by Matt Chambers and Matt Mullins of Speedquizzing VA.
The fun begins at 2:00 PM in The Tasting Room. Trivia Rounds to include General Knowledge, Music, and Specialty Themed Rounds. Prizes for winners!
