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.
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 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 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!
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 for a Cute Santa Paint & Sip Party — the perfect way to relax, sip, and get into the festive spirit this season!
Together, we’ll paint this picture using acrylics on canvas.
No painting experience needed! I’ll guide you step-by-step as you create your own seasonal masterpiece — perfect to display at home or gift to your loved ones.
🎨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-Christmas escape
📅 December 20th | 3:30–5:30pm
📍 Williamsburg Winery, 5800 Wessex Hundred, Williamsburg, VA
Spots are limited — reserve yours early!
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.
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.
Thanksgiving Buffet Menu Preview
To Start
Baby Kale Salad - Roasted Beets, Pears, Goat Cheese & Cider Vinaigrette
Fresh Fruit Platter
Honey Vanilla Yogurt with Fresh Berries
Curried Pumpkin Bisque - Spiced Pepita Seeds
Fresh Rolls & Butter
Carving Station
Roasted Turkey - Cranberry Relish
Brown Sugar Ham - Brown Sugar Honey Mustard
Accompaniments
Sage Sausage Stuffing
Glazed Sweet Potatoes
Mashed Potatoes
Three-Cheese Mac & Cheese
Green Beans Almondine
Roasted Fall Vegetable Medley
Desserts
Pumpkin Pie
Apple Streusel Pie
Pecan Pie
CANCELLATION POLICY: No refunds will be issued 7 days before the event. Last day to request a refund is November 20th.
Saturdays & Sundays during regular business hours ❄️
Step into the magic of the season at Wessex Hundred's Winter Weekends! From December 1st through January 1st, our estate will be beautifully decorated for the holidays, creating the perfect festive backdrop for your visit.
Enjoy holiday music, indulge in winter-inspired food and drink specials, cozy up by the fireplaces, and find unique gifts for everyone on your list.
Whether you’re stopping by with friends, family, or just treating yourself, Winter Weekends at Wessex Hundred is the perfect way to celebrate the season in style and comfort.
Come wander, sip, shop, and soak in the holiday spirit!
Chocolate Making Workshop
Discover the delicious world of chocolate at The Williamsburg Winery! This beginner-friendly, hands-on workshop is perfect for chocolate lovers of all ages.
Explore chocolate’s journey from bean to bar while creating handmade truffles, chocolate bark, and other sweet confections. Learn the basics of tempering chocolate, the differences between white, milk, and dark chocolate, and how to dip fruit for that perfect chocolate shell.
Each participant will take home 10 handmade truffles, plus additional chocolate treats, along with simple techniques to recreate in their own kitchen.
Whether you’re planning homemade holiday gifts, starting a new tradition, or simply treating yourself to a fun experience, join us for a delicious day of chocolate making!
Chocolate Making Workshop
Discover the delicious world of chocolate at The Williamsburg Winery! This beginner-friendly, hands-on workshop is perfect for chocolate lovers of all ages.
Explore chocolate’s journey from bean to bar while creating handmade truffles, chocolate bark, and other sweet confections. Learn the basics of tempering chocolate, the differences between white, milk, and dark chocolate, and how to dip fruit for that perfect chocolate shell.
Each participant will take home 10 handmade truffles, plus additional chocolate treats, along with simple techniques to recreate in their own kitchen.
Whether you’re planning homemade holiday gifts, starting a new tradition, or simply treating yourself to a fun experience, join us for a delicious day of chocolate making!
🎅 Brunch with Santa at The Gabriel Archer Tavern!
Join us December 6 from 11 a.m.–2 p.m. for a little holiday magic at The Williamsburg Winery! Enjoy brunch with a few seasonal specials and festive cocktails to get you in the holiday spirit.
Santa will be stopping by, but he’s a busy guy! Reserve your table between 11 a.m. and 2 p.m. to catch his visit.
✨ Reservations are available on OpenTable; book early before tables fill up!
Chocolate Making Workshop
Discover the delicious world of chocolate at The Williamsburg Winery! This beginner-friendly, hands-on workshop is perfect for chocolate lovers of all ages.
Explore chocolate’s journey from bean to bar while creating handmade truffles, chocolate bark, and other sweet confections. Learn the basics of tempering chocolate, the differences between white, milk, and dark chocolate, and how to dip fruit for that perfect chocolate shell.
Each participant will take home 10 handmade truffles, plus additional chocolate treats, along with simple techniques to recreate in their own kitchen.
Whether you’re planning homemade holiday gifts, starting a new tradition, or simply treating yourself to a fun experience, join us for a delicious day of chocolate making!
Chocolate Making Workshop
Discover the delicious world of chocolate at The Williamsburg Winery! This beginner-friendly, hands-on workshop is perfect for chocolate lovers of all ages.
Explore chocolate’s journey from bean to bar while creating handmade truffles, chocolate bark, and other sweet confections. Learn the basics of tempering chocolate, the differences between white, milk, and dark chocolate, and how to dip fruit for that perfect chocolate shell.
Each participant will take home 10 handmade truffles, plus additional chocolate treats, along with simple techniques to recreate in their own kitchen.
Whether you’re planning homemade holiday gifts, starting a new tradition, or simply treating yourself to a fun experience, join us for a delicious day of chocolate making!
Let me show you how easy these vibrant plants can be to care for. You will have plenty of choices on your favorites as well as holiday mini twinkle lights and winter decor. Create this stunning tabletop Christmas tree from all real living succulents. These homegrown beauties will adorn this Christmas tree for months and beyond. Once the holidays are over you will be able to simply remove with all instructions given to take home on how to achieve a new centerpiece for Spring.
Have fun and create!
Join us for a Cute Santa Paint & Sip Party — the perfect way to relax, sip, and get into the festive spirit this season!
Together, we’ll paint this picture using acrylics on canvas.
No painting experience needed! I’ll guide you step-by-step as you create your own seasonal masterpiece — perfect to display at home or gift to your loved ones.
🎨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-Christmas escape
📅 December 20th | 3:30–5:30pm
📍 Williamsburg Winery, 5800 Wessex Hundred, 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!
Chocolate Making Workshop
Discover the delicious world of chocolate at The Williamsburg Winery! This beginner-friendly, hands-on workshop is perfect for chocolate lovers of all ages.
Explore chocolate’s journey from bean to bar while creating handmade truffles, chocolate bark, and other sweet confections. Learn the basics of tempering chocolate, the differences between white, milk, and dark chocolate, and how to dip fruit for that perfect chocolate shell.
Each participant will take home 10 handmade truffles, plus additional chocolate treats, along with simple techniques to recreate in their own kitchen.
Whether you’re planning homemade holiday gifts, starting a new tradition, or simply treating yourself to a fun experience, join us for a delicious day of chocolate making!
Toast to 2027 at Gabriel Archer Tavern! 🥂✨
Join us on December 31, 2026, for an elegant New Year’s Eve dinner featuring a chef-curated seasonal menu.
• An amuse-bouche to begin
• Three courses: choose from three appetizers, three entrées, and two desserts
• $85 per person, plus tax and gratuity
• Add wine pairings for $35 per person
Reserve your table on OpenTable
