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.
Spring is in the air at Wessex Hundred! Join us every weekend for curated wine flights, seasonal bites at the Tavern, and all the spring vibes. Soak up the sunshine, sip chilled wines, and enjoy the perfect springtime escape.
Free event, no tickets.
5/2 saturday 4-7pm Hannah J
5/9 saturday 4-7pm Lane Rice
5/16 saturday 4-7pm Pancho Villa
5/23 saturday 4-7pm Felicia Hoyos
5/30 saturday 4-7pm Lane Rice
6/6 saturday 4-7pm Sam Riddle
6/13 saturday 4-7pm Hannah J
6/20 saturday 4-7pm Poncho Villa
6/27 saturday 4-7pm Sam Riddle
7/4 saturday 4-7pm Lane Rice
7/11 saturday 4-7pm Pancho Villa
7/18 saturday 4-7pm Hannah J
7/25 saturday 4-7pm Felicia Hoyos
8/1 saturday 4-7pm Hannah J
8/8 saturday 4-7pm Sam Riddle
8/15 saturday 4-7pm Love Cats
8/21 friday 4-7pm Pancho Villa
8/22 saturday 4-7pm Felicia Hoyos
8/29 saturday 4-7pm Nathan Lienard
9/5 saturday 4-7pm Sam Riddle
9/12 saturday 4-7pm Lane Rice
9/19 saturday 4-7pm Felicia Hoyos
9/26 saturday 4-7pm Pancho Villa
10/3 saturday 4-7pm Sam Riddle
10/10 saturday 4-7pm Lane Rice
10/17 saturday 4-7pm Pocho Villa
10/24 saturday 4-7pm Sam Riddle
10/31 saturday 4-7pm Sam Riddle
11/7 saturday 4-7pm Felicia Hoyos
11/14 saturday 4-7pm Sam Riddle
11/21 saturday 4-7pm Nathan Lienard
11/27 friday 4-7pm Sam Riddle
11/28 saturday 4-7pm Lane Rice
Come out for an evening at the winery with live music, great food by Chef Chad 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!
Join us at The Williamsburg Winery for a special Vet First Information & Program Day with Vet First, Inc., a one-of-a-kind nonprofit dedicated to supporting U.S. Veterans through agriculture, education, and community service.
Vet First operates a working garden right here on the winery property, where Veterans help grow sustainable, organic produce that is donated to local food banks.
This free, public event is an opportunity for Veterans to learn more about their no-cost agricultural education program. The program offers hands-on experience, recognized training hours, and preparation for USDA- and NRCS-aligned credentials.
Guests will have the chance to meet educators and community partners, enjoy light bites and refreshments, and explore how agriculture can be a pathway to learning, service, and connection through land stewardship and meaningful work.
To learn more about Vet First Inc. and their Agricultural Education Program, email jmershonn@vetfirstinc.com.
10:00 AM – 1:00 PM (EST)
Williamsburg Winery – Westbury Hall
5800 Wessex Hundred, Williamsburg, VA 23185
FREE • Public • Veterans • Families • Professionals Welcome
Small bites will be available along with refreshments
Discover a Veteran-focused agricultural education and training program designed to reconnect service, land stewardship, and community impact.
Participants gain access to recognized training hours, hands-on learning pathways, and preparation for USDA and NRCS-aligned credentials—all at no cost.
Learn • Connect • Serve Again
Industry-aligned education
Conservation & sustainability training
Credential preparation
Community partners & educators on-site
Hosted by Vet First, Inc.
Sponsors & Partners:
VDACS • Virginia DVS • iCEV • Bubo Learning Design • TSC Enterprise
Virginia Tech Agriculture Research & Extension Centers • William & Mary
Virginia Peninsula Foodbank • Foodbank of SE Virginia & Eastern Shore
Transform a reclaimed wine bottle into a living sculptural piece rooted in both plant science and creative design.
In this hands-on workshop, participants will create a one-of-a-kind succulent arrangement nestled into a thoughtfully prepared wine bottle vessel. Led by Melissa Tebbenhoff of Rusted Rabbitt Living Designs, this experience blends botanical education with artistic process, offering insight into how succulents grow, adapt, and thrive in unconventional yet intentional environments.
As both a succulent grower and living design artist, Melissa guides participants through plant selection, balance, and composition while sharing practical growing knowledge that supports long-term plant health. Each arrangement is built using a special plant-friendly adhesive, allowing the succulents to establish gently while remaining adaptable for future replanting.
This workshop is more art-forward in nature while still grounded in horticultural understanding, making it approachable for beginners and enriching for seasoned plant lovers. The result is a sculptural, living piece that continues to evolve long after the class concludes.
Workshop Includes:
– Prepared wine bottle vessel
– Assortment of homegrown succulents
– Preserved moss
– Plant-safe adhesive
– Natural botanical accents
– Care instructions and ongoing guidance
When the arrangement outgrows its vessel, participants will learn how to transition their succulents into future living designs—extending the life of the piece beyond the workshop.
*****PLEASE NOTE THE ADDRESS OF THE LOCATION. THIS IS LOCATED AT THE WINE BAR AND TASTING ROOM IN CW MERCHANT SQAURE. THIS IS NOT AT THE MAIN WINERY LOCATION*********
Uncorked & Unplugged returns Saturday, June 6, starring DAVID COOK, HOWIE DAY, and VERTICAL HORIZON! Don't miss this intimate, acoustic concert to kick off the summer LIVE at the Williamsburg Winery. VIP exclusive seating is available.
Stop by early to enjoy a glass of wine or our many vendors before the show.
Doors open at 12 PM.
SET-TIMES:
Howie Day 5:15
David Cook 6:15
Vertical Horizon 7:15
Please Note: This show will take place onsite at the Williamsburg Winery and seating is provided on a first-come, first-serve basis. 21+ welcome. Please drink responsibly.
IMPORTANT INFO:
FREE PARKING
21+ welcome
Rain or shine
No firearms or weapons of any sort permitted onsite
NO COOLERS OR OUTSIDE FOOD
Tickets are available while supplies last
Wine, Beer, Cider, Non-Alcoholic beverages, and Food will be available for purchase onsite via credit card or cash
Each guest must present their ticket(s) and a government issued photo ID prior to entering the venue
Join us in person for Plant Bingo—where greenery meets fun and you could win cool plant prizes!
Join Us for Plant Bingo!
Ready for some green-thumb fun?
Plant Bingo is happening in person, and it's the perfect way to chill with fellow plant lovers. Bring your love for all things leafy and get ready to shout “Bingo!” while surrounded by an array of beautiful plants both succulents and a variety of indoor houseplants.
It’s a laid-back, fun event where you can meet new friends and maybe even snag some cool indoor plant and succulent insights.
Don’t miss out on the plant party!
Everyone receives a plant and planter of their choice.
Many wine specials are available from the winery.
Grab a friend fast as this popular event will sell out quickly due to limited spaces available.
Tickets: https://www.eventbrite.com/e/plant-bingo-tickets-1989795338421?aff=ebdsoporgprofile
Succulent Birdhouse Workshop at Wessex Hundered Tasting Room
Create a charming living sculpture in this hands-on workshop where nature, whimsy, and design intersect. In this class, you’ll transform a preserved moss birdhouse into a lush succulent arrangement, blending living plants with natural textures for a piece that feels both playful and artful.
Your base registration includes:
- Guided instruction from the grower and artist
- A moss birdhouse as your creative base
- A curated selection of healthy, homegrown succulents
- Soil and design materials
- Access to a thoughtfully gathered collection of natural adornments including moss, stones, dried florals and feathers and other organic elements
- Succulent care guidance to help your piece thrive
During the workshop, participants are welcome to expand their design by selecting additional succulents beyond the base selection. These enhancements are entirely optional and can be easily settled at the end of class, allowing the creative flow of the workshop to remain uninterrupted.
✨ Most participants spend between$68-$88 total, depending on how they choose to personalize their birdhouse.
No prior experience is needed. Come create, connect, and leave with a living work of art—one that feels at home in both garden and gallery alike.
Celebrate America's 250th birthday — with a paintbrush in hand and a glass of your favorite wine nearby!
Join us on June 28th for a fun, relaxed painting party at Williamsburg Winery Tasting Room in Colonial Williamsburg. No experience needed — just show up ready to create your own beautiful canvas featuring a bold navy 250, white stars, and a gorgeous bouquet of red and white flowers. Perfect for the season and a keepsake you'll actually want to hang on your wall.
🎨 All painting supplies included
🍷 Wine and drinks available for purchase at the bar
🌸 Take home your finished painting
👯 Great for date nights, friend groups, and solo adventurers alike
To see the host and how past events went please visit my facebook page https://www.facebook.com/share/1Avf78NnNo/?mibextid=wwXIfr
Spots are limited — reserve yours early!
Join us in person for Plant Bingo—where greenery meets fun and you could win cool plant prizes! Plus leave with a plant and planter by RR.
Join Us for Plant Bingo!
Ready for some green-thumb fun?
Plant Bingo is happening in person, and it's the perfect way to chill with fellow plant lovers. Bring your love for all things leafy and get ready to shout “Bingo!” while surrounded by an array of beautiful plants both succulents and a variety of indoor houseplants.
It’s a laid-back, fun event where you can meet new friends and maybe even snag some cool indoor plant and succulent insights.
Don’t miss out on the plant party!
Everyone receives a plant and planter of their choice.
Many wine specials are available from the winery.
Grab a friend fast as this popular event will sell out quickly due to limited spaces available.
Experience a night of culinary artistry and connection at our Chef ’s Notebook Series. Treat yourself to an exclusive evening that promises:
An Opportunity to connect with Chef Chad Bergeron as he shares his inspirations behind each dish.
An Intimate 4-Course Dinner thoughtfully paired with exquisite wines from our collection.
Reservations through OpenTable or by calling the host stand at (757) 564-8869.
$70++ per person
Dive into your creative side this summer!
Join us on July 26th at the Williamsburg Winery Tasting Room for a fun, laid-back painting party where we'll bring a gorgeous jellyfish to life in dreamy blues and teals.
No experience needed — just come ready to relax, create, and leave with a painting you'll actually love. Our instructor will guide you step by step through the full piece, so even first-timers will walk away feeling like an artist.
🪼 All painting supplies included
🍷 Wine and drinks available for purchase at the bar
🎨 Take home your finished canvas
👯 Perfect for date nights, girls' nights, or a solo creative escape
📅 July 26th | 3:30–5:30 PM
📍 Williamsburg Winery Tasting Room, Williamsburg, VA
To see the host and how past events went please visit my facebook page https://www.facebook.com/share/1Avf78NnNo/?mibextid=wwXIfr
Spots are limited — reserve yours early!
Cannon Country 107.9 FM and The Williamsburg Winery are excited to present the third annual Cannon Country Fest on August 1st! 2026’s event marks a return home to Williamsburg, and what better way to celebrate that than with homegrown talent. Williamsburg’s own Canaan Smith will be headlining, with an additional lineup of local talent announcing soon. Dust off your cowboy boots, mark your calendars, and get your tickets now for the show of the summer!
General Admission Ticket Info:
One (1) ticket to the show with first-come, first-served seating on Wessex Lawn
Kids under 12 are FREE in General Admission
FREE PARKING
Saturday 21+ ONLY VIP Ticket Info:
One (1) ticket to the show, with preferred seating and viewing
One (1) commemorative wine glass
One (1) complimentary pour of wine
Access to the Exclusive VIP Area with a private full bar and private restroom
FREE PARKING
Join us in person for Plant Bingo—where greenery meets fun and you could win cool plant prizes! Plus leave with a plant and planter by RR.
Join Us for Plant Bingo!
Ready for some green-thumb fun?
Plant Bingo is happening in person, and it's the perfect way to chill with fellow plant lovers. Bring your love for all things leafy and get ready to shout “Bingo!” while surrounded by an array of beautiful plants both succulents and a variety of indoor houseplants.
It’s a laid-back, fun event where you can meet new friends and maybe even snag some cool indoor plant and succulent insights.
Don’t miss out on the plant party!
Everyone receives a plant and planter of their choice.
Many wine specials are available from the winery.
Grab a friend fast as this popular event will sell out quickly due to limited spaces
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!
