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.
7/4 saturday 4-7pm Lane Rice
7/11 saturday 4-7pm Pancho Villa
7/18 saturday 4-7pm Lane Rice
7/25 saturday 4-7pm Felicia Hoyos
8/1 saturday 4-7pm Lane Rice
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!
Spend your Saturday evenings surrounded by vineyard views, live music, and the relaxed charm of summer at The Williamsburg Winery. Dine al fresco on the Gabriel Archer Tavern patio, sip estate wines beneath the bistro lights on Wessex Lawn, or settle in at the Pavilion with a glass in hand while local musicians provide the soundtrack to your evening. Whether you're joining us for dinner, drinks, or simply to unwind, there's no better way to celebrate the season.
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
Enjoy a cheesemaking experience designed for everyone from absolute beginners to experienced home cooks. In just one hour, you’ll learn how to transform simple grocery store ingredients into fresh, delicious cheese from start to finish—no special equipment, no prior experience, and no raw milk required.
Guided by an expert cheesemaker with over 15 years of teaching experience, this class weaves together the rich history of cheesemaking with a clear, foolproof method you can easily recreate in your own kitchen. You’ll discover how traditional techniques translate beautifully into modern home cooking using tools you likely already have on hand.
This versatile, beginner-friendly cheese is the perfect foundation for a wide range of dishes—from sweet desserts to creamy spreads, from Italian favorites to crowd-pleasing party dips, and more. You will learn how cheesemaking can be adapted to suit your needs, including the easiest way to create lactose-free cheese. YAY!
Whether you’re looking for a memorable winery experience or a new skill you can take home and use again and again, this class offers the perfect blend of history, practical techniques, and delicious results—guaranteed.
Please note: There is a $10 materials fee payable to the Instructor upon arrival
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 including Cawson’s Coop. Dust off your cowboy boots, mark your calendars, and get your tickets now for the show of the summer!
Live Music Lineup:
2:00 PM – Sam Riddle
3:30 PM – Lane Rice
5:00 PM – Cawson's Coop Band
6:30 PM – Canaan Smith
Bring your friends, your favorite blanket or lawn chair, and spend the day enjoying live country music in the vineyard. Sip award-winning Virginia wines, enjoy local beer and cider, grab delicious food from onsite vendors, and soak up one of the best summer events in Williamsburg.
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
Last Sip of Summer
Summer doesn't last forever — but this painting will.
Join us on August 8th at the Williamsburg Winery Tasting Room for a laid-back painting party that captures everything we love about these last golden days. We'll paint a juicy watermelon slice on the beach, framed by a lush monstera leaf and a vibrant hibiscus flower — with a sweet heart-shaped hole right through the middle, because summer deserves to be felt, not just seen.
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
📅 August 8th | 3:30-5:30pm
📍 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
Coming with a group of 4 or more? Message me for a group rate.
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
Private & Corporate Events Open House
Sunday, August 16 | 12:00–4:00 PM
Explore The Williamsburg Winery's beautiful private event spaces at your own pace during our Open House. Meet with our events team, enjoy a complimentary welcome splash, and discover how we can help bring your next celebration or corporate gathering to life.
Whether you're planning a birthday, bridal shower, rehearsal dinner, holiday party, anniversary, retirement celebration, or business event, this is the perfect opportunity to tour our venues, ask questions, and learn about booking opportunities. No RSVP required; stop by and be inspired!
Enjoy a cheesemaking experience designed for everyone from absolute beginners to experienced home cooks. In just one hour, you’ll learn how to transform simple grocery store ingredients into fresh, delicious cheese from start to finish—no special equipment, no prior experience, and no raw milk required.
Guided by an expert cheesemaker with over 15 years of teaching experience, this class weaves together the rich history of cheesemaking with a clear, foolproof method you can easily recreate in your own kitchen. You’ll discover how traditional techniques translate beautifully into modern home cooking using tools you likely already have on hand.
This versatile, beginner-friendly cheese is the perfect foundation for a wide range of dishes—from sweet desserts to creamy spreads, from Italian favorites to crowd-pleasing party dips, and more. You will learn how cheesemaking can be adapted to suit your needs, including the easiest way to create lactose-free cheese. YAY!
Whether you’re looking for a memorable winery experience or a new skill you can take home and use again and again, this class offers the perfect blend of history, practical techniques, and delicious results—guaranteed.
Please note: There is a $10 materials fee payable to the Instructor upon arrival.
Wedding Open House
Sunday, August 30 | 1:00–4:00 PM
Join us at The Williamsburg Winery for our Wedding Open House and discover everything you need to plan your dream wedding. Begin your visit at Wessex Hall, then enjoy a self-guided tour of our beautiful event spaces and scenic vineyard property. Meet with our wedding team, connect with talented local wedding vendors, and gather inspiration for every detail of your special day.
Enjoy complimentary cookies and refreshments, or purchase a glass of rosé or a mimosa from our cash bar as you explore.
Whether you're newly engaged or finalizing your plans, we look forward to showing you how The Williamsburg Winery can bring your wedding vision to life.
Colonial K9 Classic Returns to The Williamsburg Winery
Get ready for a tail-wagging weekend as the Colonial K9 Classic returns to The Williamsburg Winery on September 12-13! Hosted by our friends at Muddy Marley's Dog Wash in partnership with DockDogs, this exciting two-day event brings incredible canine athletes to our winery for a weekend of high-flying fun.
Watch dogs compete in Big Air, Extreme Vertical, Speed Retrieve, Iron Dog, and the thrilling Big Air Finals. While you're here, enjoy local vendors, food trucks, and our beer and wine garden, all set against the backdrop of our beautiful vineyard.
Whether you're competing, cheering on the dogs, or simply looking for a unique day out with family and friends, the Colonial K9 Classic is an event you won't want to miss.
Registration for competitors is now open through DockDogs.
September 12-13 | The Williamsburg Winery
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!
