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*********
Get ready for a wickedly fun day of wine, movement, and memories at Wicked Wine Run® at The Williamsburg Winery on May 30, 2026. Set among rolling vineyards in the heart of Virginia Wine Country, this unforgettable experience blends fitness, friendship, and fantastic wine—no matter how fast (or slow) you go.
Founded in 2013, Wicked Wine Run is the longest-running and most participated wine run in the country. With a passion for creating joyful, one-of-a-kind events, Wicked Wine Run invites participants to run, walk, skip, or dance their way through some of the most scenic vineyards nationwide—glass in hand and smiles guaranteed.
Choose your adventure with a 1K or 5K race option—or do both if you’re feeling extra spirited. Yes, you can absolutely walk the 5K. This event is all about having fun, soaking in the views, and enjoying great wine with your favorite people.
1K participants enjoy wine tastings along the course and at the finish line, while 5K finishers are rewarded with a full glass of wine, a brand-new 2026 event shirt, and an exclusive finisher medal. All participants receive access to the lively after-party, where the celebration continues long after you cross the finish line.
With over 20 years of multifaceted event production experience, Wicked Wine Run is known for creating experiences that keep besties coming back year after year. Recognized by CBS, Self Magazine, Runner’s World, Greatist, Fox, Buzzfeed, and more, this is more than a race—it’s a vineyard party you don’t want to miss.
Come for the wine. Stay for the vibes. Leave with memories (and maybe a little wine glow). 🍷🏃♀️✨
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.
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.
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!
