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.
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!
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!
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.
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.
Join us on August 23rd to soak up the final warmth of the season and paint bright, cheerful sunflowers on a functional canvas tote bag! We'll bring the spirit of late summer to life on a sturdy, eco-friendly bag you can actually take out into the world for farmers' markets, books, or everyday errands.
No experience needed — just come ready to relax, create, and leave with a wearable piece of art 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 and canvas tote bags included
🍷 Drinks available for purchase
🎨 Take home your finished custom tote bag
👯 Perfect for date nights, girls' nights, or a solo creative escape
📅 August 23rd | 3:30-5:30pm
📍Williamsburg Winery Tasting Room, 427 W Duke of Gloucester, 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!
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.
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.
The Colonial K9 Classic event, presented by Muddy Marley's Dog Wash combines the thrill of a live Dock dog diving competition, a wine and beer garden and delicious food. Located on the grounds of the beautiful and iconic Williamsburg Winery, you'll soak in the outdoor activities be up close and personal to the excitement all while enjoying a cold beverage (or two), paired with some amazing food and all things dogs!
Need a break from the excitement? Enjoy visiting the many information tents with local pet-related care information and other community vendors on site.
FREE to attend!
For more information about the event and places to stay in Williamsburg, go to www.colonialk9classic.com!
Sat. Sep 12 2026
Onsite Registration/Practice – 8:00 am
Big Air Wave #1 – 9:00 am
Big Air Wave #2 – 10:30 am
Big Air Wave #3 – 12:00 pm
Big Air Wave #4 – 1:30 pm
Extreme Vertical Competition – 3:30 pm
Sun. Sep 13 2026
Onsite Registration/Practice – 8:00 am
Big Air Wave #5 – 9:00 am
Big Air Wave #6 – 10:30 am
Big Air Wave #7 – 12:00 pm
Speed Retrieve Competition – 2:00 pm
Big Air Finals – 4:30 pm (Divisional Finals Format)
Join us on September 12th at the Williamsburg Winery Tasting Room to welcome the season with a cozy, colorful painting session. We'll bring a warm orange pumpkin and a moody blue-gray pumpkin together with a bright sunflower — all tied together by a curling vine that spells out "Hello Fall" across the canvas.
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
📅 September 12th | 3:30–5:30pm
📍 Williamsburg Winery Tasting Room, 5800 Wessex Hundred, Williamsburg, VA
Coming with a group of 4 or more? Message me for a group rate.
Spots are limited — reserve yours early!
Celebrate the flavors and traditions of Oktoberfest at Gabriel Archer Tavern with a festive evening of authentic cuisine, exceptional wines, and warm hospitality.
Join us for a special Oktoberfest Dinner featuring a chef-crafted menu inspired by classic German favorites, thoughtfully paired with selections from The Williamsburg Winery. Gather with friends and family to enjoy a seasonal celebration filled with hearty fare, great wine, and the spirit of Oktoberfest.
Menu coming soon!
Reserve your table by calling Gabriel Archer Tavern at (757) 564-8869 or book online through OpenTable.
Let’s design this beautiful living centerpiece using a living pumpkin and home grown succulents.All supplies are provided.No carving needed.
Let me teach you all about SUCCULENTS! I grow 1000's of colorful and EXOTIC types for you to choose from!
PLUS pick your favorite PUMPKIN from a wide variety.
We will adorn the top of our pumpkins (NO CARVING) with MOSS and your beautiful succulents to build a long lasting arrangement.
Take home Care Card and succulent lesson are included.
No prior experience needed.
Wine not included in ticket registration.
PLEASE NOTE THE LOCATION IS NOT THE MAIN WINERY. THIS IS HELD AT THE MERCHANT SQAURE WINE BAR AND TASTING ROOM
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.
Please note the address of the event. This is held at the tasting room and wine bar in the charming historic Merchant Square.
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.
Wednesday, October 14th | 5:45 PM | Cocktail Hour with welcome splash & cash bar 5:45-6:15 | Dinner at 6:15 PM |
Celebrate the beauty of the season with our Dinner in the Vineyard, set among the golden hues of our estate Albariño vineyard. Your evening begins with a sparkling toast upon arrival, followed by a leisurely walk to the vines where a long, table awaits beneath the crisp autumn sky.
As twilight settles over the vineyard, indulge in a thoughtfully curated menu by Chef Chad, each pairing designed to highlight the harmony of food, wine, and the season.
MENU PREVIEW TO FOLLOW
Between the vines, you’ll enjoy the warmth of good company, the rustle of leaves, and the serene magic that only harvest season can bring.
One of our most beloved traditions, Dinner in the Vineyard, is a celebration of wine, food, and the land that brings them together.
Seating is limited - reserve your place today for an unforgettable night.
No menu substitutions are available.
Join us on October 17th at the Williamsburg Winery Tasting Room for a sweet and playful painting session celebrating the season. We'll bring to life an adorable, friendly ghost cradling a pumpkin vase overflowing with warm fall flowers — spooky season's cutest side, no scares included.
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 cozy fall afternoon
📅 October 17th | 3:30–5:30pm
📍 Williamsburg Winery Tasting Room, 427 W Duke of Gloucester, Williamsburg, VA
Coming with a group of 4 or more? Message me for a group rate.
Spots are limited — reserve yours early!
🌱 Plant Bingo is coming to Williamsburg Winery – and you’re invited to the exclusive Fall launch! 🌱
Join Rusted Rabbitt Living Designs for an evening of fun, learning, and plants in the charming historic setting of Merchants Square. This is the official launch of our Plant Bingo Fall series — three special nights filled with laughter, plant tips & tricks, and beautiful succulent art!
What to Expect:
• Play multiple rounds of Plant Bingo while learning pro houseplant and succulent care tips
• Admire (and shop) stunning succulent art creations by Rusted Rabbitt
• Educational & entertaining facilitation with Melissa
• Every ticket holder receives a beautiful succulent to take home!
• Relax in the lovely winery atmosphere surrounded by shops and restaurants.
No wine is included with tickets. Grab a glass on your own if you’d like while you play!
This is a perfect girls’ night, date night, or solo plant-lover outing in one of Williamsburg’s most charming locations. Space is limited — tickets going fast!
Fall Fest at the Vineyard
Celebrate the arrival of autumn at The Williamsburg Winery on Saturday, October 24, from 12:00 PM to 6:00 PM. Spend the day with family and friends enjoying the beauty of Virginia wine country while taking part in seasonal activities, local flavors, and live entertainment.
The day's festivities include grape stomping, live music by Sam Riddle, a Low Country Boil and fresh oysters*, award-winning Virginia wines, and a curated selection of local artisan vendors. Guests can also enjoy classic lawn games like cornhole and bocce ball while relaxing on our scenic vineyard grounds.
Admission is free, and the event is family-friendly and pet-friendly, making it the perfect fall outing for all ages.
*Event food available for purchase 12-4 PM, after 4 PM food will be available at the Tavern or in the Wine Tasting Room.
Planning to stay the weekend? Book a room at Wedmore Place Hotel, located on the winery property, and enjoy being just steps away from all the Fall Fest activities.
Create this Living Succulent Arrangement with me at the BEAUTIFUL Williamsburg Winery.
Pick your pumpkin and come enjoy an evening learning all about these homegrown succulents. I will bring all the most beautiful for you to choose from. Then we will create this sustainable arrangement with many options to customize.
Grab a warm Fall inspired beverage, mulled wine, the various flights and wine tastings to fully celebrate Fall with this fun and unique experience.
NO REFUNDS ARE AVAILABLE OR TRANSFERS
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.
6:00 PM – 8:00 PM (Last tour departs at 8:00 PM)
Dare to descend into the dark? Step into our Haunted Cellar for a chilling tour through the depths of the winery, where restless spirits stir and shadows whisper.
Tours will be filled on a first-come, first-served basis.
Costumes encouraged (no masks or weapon-like props permitted).
This is a 21+ event only. No children permitted.
Tickets Required. There is NO Monster Ball on Friday, Oct 30th, only Sat Oct 31st. This is a separate ticket.
Will you escape… or will the cellar claim you?
Step into our Haunted Cellar for a chilling tour through the depths of the winery, where restless spirits stir and shadows whisper.
6:00 PM – 10:00 PM (Last tour departs at 8:30 PM)
Dare to descend into the dark? Step into our Haunted Cellar for a chilling tour through the depths of the winery, where restless spirits stir and shadows whisper. If you make it out alive, the night continues with our Monster Ball, a sinister celebration featuring eerie cocktails, and a chance to dance with creatures of the night.
Your ticket includes access to 1 Haunted Cellar Tour and access to the Monster Ball.
Tours will be filled on a first-come, first-served basis.
Costumes encouraged (no masks or weapon-like props permitted).
This is a 21+ event only. No children permitted.
Will you escape… or will the cellar claim you?
Join us on October 31st at the Williamsburg Winery Tasting Room for a playfully spooky painting session, perfect for getting into the Halloween spirit before the trick-or-treating starts. We'll paint a silhouetted haunted house against a bold orange sky, with a crescent moon and bat perched above, a few friendly ghosts drifting around the house, and bare, twisting tree branches framing the whole scene.
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.
This is a perfect pre-trick-or-treat activity — paint your masterpiece, then head out for a spooky night with plenty of time to spare before the little ones (or you!) hit the streets for candy.
🦇 All painting supplies included
🍷 Wine and drinks available for purchase at the bar
🎨 Take home your finished canvas
👻 Perfect for a fun Halloween afternoon before trick-or-treating
📅 October 31st | 3:30–5:30pm
📍 Williamsburg Winery Tasting Room, 5800 Wessex Hundred, Williamsburg, VA
Coming with a group of 4 or more? Message me for a group rate.
Spots are limited — reserve yours early!
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.
Join us on November 14th at the Williamsburg Winery Tasting Room for a cozy autumn painting session designed with couples in mind. We'll paint two sweet, wide-eyed owls perched side by side on a branch, surrounded by golden fall blossoms and framed by soft blue sky — a piece that's as much about connection as it is about color.
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. This diptych design is perfect for pairs — each canvas stands beautifully on its own, but side by side they tell one story.
🦉 All painting supplies included
🍷 Wine and drinks available for purchase at the bar
🎨 Take home your finished canvas — yours and theirs, a set
👯 Perfect for date nights, anniversaries, or any twosome who love to create together
📅 November 14th | 3:30–5:50pm
📍 Williamsburg Winery Tasting Room, 5800 Wessex Hundred, Williamsburg, VA
Coming with a group of 4 or more? Message me for a group rate.
Spots are limited — reserve yours early!
Join us on November 21st at the Williamsburg Winery Tasting Room for a warm, nostalgic painting session that captures the coziest parts of the season. We'll paint an orange and blue-gray pumpkin in the background, a steaming cup of your favorite hot drink and a slice of pumpkin pie at the center, and a soft knitted scarf draped in front, scattered with oak leaves and acorns.
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 cozy pre-Thanksgiving escape
📅 November 21st | 3:30–5:30pm
📍 Williamsburg Winery Tasting Room, 427 W Duke of Gloucester, Williamsburg, VA
Coming with a group of 4 or more? Message me for a group rate.
Spots are limited — reserve yours early!
Celebrate Thanksgiving with wine, delicious food, and comfort at The Williamsburg Winery! Gather with family and friends in Wessex Hall as we share a Thanksgiving meal specially curated by Chef Chad. Our buffet will be full of traditional favorites and home-cooked touches, paired with Williamsburg Winery wines* and seasonal cocktails*.
Your reservation includes access to the buffet for one person. Children's pricing (12 and under) is available to reserve. Children under 3 are free. Minimum 2 people per reservation, maximum 8 people. Regular, Children 12 & Under, and Children Under 3 options available. Please make sure to reserve tickets for all adults and children in your party, including any children under 3 years old, so that we may set our tables and seating charts accordingly.
*Tickets do not include drinks. Wine, beer, cocktails, sodas, and juices; are purchased separately.
MENU PREVIEW TO COME
CANCELLATION POLICY: No refunds will be issued 7 days before the event. Last day to request a refund is November 20th.
