Williamsburg Whiskey & Wine Weekend – June 27-29

Welcome to a Williamsburg weekend of whiskey and wine, June 27-29, 2025! Indulge in three days of tastings, classes, tours, live music, and more.

Get your Williamsburg Whiskey & Wine Digital Pass to the weekend’s activities, including tasting tours, educational classes, and special events. Attendees can visit multiple locations throughout Williamsburg to complete a digital pass and earn prizes during the weekend.

The full schedule is available at williamsburgwhiskeywine.com. The event is sponsored by the City of Williamsburg and and produced by AVAdventure Productions.

FRIDAY, JUNE 27

WINE TASTING AT THREE SISTERS BOUTIQUE

Friday, June 27 from 10 am – 6 pm
525 Prince George Street
Stop by for a complimentary tasting and enjoy a 10% discount on all in-stock wine. This tasting event features the 2021 Southern Belle “Precious” Syrah, aged in Pappy Van Winkle bourbon barrels. More Info

COLONIAL WILLIAMSBURG MEAD TASTING AT BRICK & VINE

Friday, June 27 from 2-4 pm
431 W Duke of Gloucester Street
Sample a variety of Colonial Williamsburg meads made by Silver Hand Meadery. Free.

PINOT NOIR TASTING AT BLUE TALON BISTRO

Friday, June 27 at 5 pm
420 Prince George Street
Join world traveling wine expert Matt Earnhardt on a guided tasting of selected international Pinot Noirs. Tickets for this event are $25 and include a guided wine tasting and light snacks, purchase tickets here.

JAZZ JAM AT SILVER HAND MEADERY

Friday, June 27 from 6-8 pm
224 Monticello Ave
Bring your voice, your instrument, and your excitement for delicious mead and come jam out with the crew at Silver Hand Meadery! Enjoy this free jazz jam hosted by Guitarist Tony Mata and Silver Hand owner Glenn Lavender. No tickets or reservations are required for this free event.

FREE MOVIE SCREENING – WINE ON FILM: SIDEWAYS

Friday, June 27 at 7:30 pm
Williamsburg Library, 525 Prince George St
Two middle-aged men embark on a spiritual journey through Californian wine country. One is an unpublished novelist suffering from depression, and the other is only days away from walking down the aisle. Rated R, 127 minutes. No tickets or reservations are required for this free event.

FREE MOVIE SCREENING – WISKEY ON FILM: SKYFALL

Friday, June 27 at 7:30 pm
Kimball Theatre, 428 W Duke of Gloucester St.
When Bond’s latest assignment goes gravely wrong, agents around the world are exposed and MI6 headquarters is attacked. While M faces challenges to her authority, it’s up to Bond, aided only by field agent Eve, to locate the mastermind behind the attack. Rated PG-13, 143 minutes. No tickets or reservations are required for this free event.

SATURDAY, JUNE 28

WINE TASTING AT THREE SISTERS BOUTIQUE

Saturday, June 28 from 10 am – 6 pm
525 Prince George Street
Stop by for a complimentary tasting and enjoy a 10% discount on all in-stock wine. This tasting event features the 2021 Southern Belle “Precious” Syrah, aged in Pappy Van Winkle bourbon barrels. More Info

COPPER FOX DISTILLERY 20TH ANNIVERSARY WEEKEND

Saturday, June 28, All day
901 Capitol Landing Road
Join Copper Fox as they raise a glass to 20 years of innovation, craftsmanship, and community at Copper Fox Distillery!
COUSINS MAINE LOBSTER TRUCK, Saturday from 12-7 pm
Savor fresh, buttery lobster rolls and coastal flavors from the nationally acclaimed food truck.
LIVE MUSIC: CK BAND, Saturday from 3-6 pm
Enjoy a lively afternoon set from local favorites, the CK Band, blending classic rock, soul, and blues with high-energy fun.
Reservations and tickets are not required. For more details, visit the Copper Fox website.

COCKTAIL CLASS: CLASSIC COCKTAILS

Saturday, June 28 at 1 pm
Amber Ox Public House – 525 Prince George St
Join cocktail expert Greg Benson in an intimate class where participants will mix – and drink! – their own cocktails while learning from an expert bartender. The Saturday class will feature instruction on creating two classic cocktails, the Old Fashioned and the Mint Julep. This event takes place in The Study at Amber Ox, and each ticket covers instruction and two cocktails. Tickets are $50 and are available here.

COLONIAL WILLIAMSBURG MEAD TASTING AT BRICK & VINE

Saturday, June 28 from 2 – 4 pm
431 W Duke of Gloucester St
Sample a variety of Colonial Williamsburg meads made by Silver Hand Meadery for free tastings!

DRINK & DESIGN WITH PAINT ON POTTERY

Saturday, June 28 at 7 pm
W&M Entrepreneurship Hub, 249 Richmond Road
Express your artistic self while enjoying wine at this unique social event! Participants will be provided materials to paint their own large stem wine goblets from Paint on Pottery. Tickets include all materials to create your own goblet, and wine will be available for purchase at the event. Tickets are $35 are available here.

COCKTAILS AND COMEDY AT ILLY CAFE

Saturday, June 28 at 7 pm doors, 7:30 pm show
435 W Duke of Gloucester St
Illy Café transforms into an after hours comedy club! This free showcase features an all-star lineup of touring stand-up comedians including headliners Kim Nario, Amber Hendrix, and Randolph Washington Jr. This event is free and for ages 18+. No tickets are required. Seating is available on a first-come, first-seated basis starting at 7pm. Food and drinks will be available for purchase during the show.

SUNDAY, JUNE 29

COPPER FOX DISTILLERY 20TH ANNIVERSARY WEEKEND

Sunday, June 29, All day
901 Capitol Landing Road

Join Copper Fox as they raise a glass to 20 years of innovation, craftsmanship, and community at Copper Fox Distillery!
MOTO CREPES FOOD TRUCK, Sunday from 12-6 pm
Offering sweet or savory crepes & freshly squeezed lemonade in a perfect blend of novelty and nostalgia.
LIVE MUSIC: THE GENERATIONS TRIO, Sunday from 2-5 pm
The Generations Trio performs classic jazz standards and thoughtful, modern arrangements of rock and pop songs.
Reservations and tickets are not required. For more details, visit the Copper Fox website.

COCKTAIL CLASS: MODERN COCKTAILS AT AMBER OX

Sunday, June 29 at 1 PM
525 Prince George Street
Join cocktail expert Greg Benson in an intimate class where participants will mix – and drink! – their own cocktails while learning from an expert bartender. The Sunday class will feature instruction on creating two modern cocktails, the Black Manhattan and the Paper Plane. This event takes place in The Study at Tickets are $50 and are available here

WHISKEY & WINE TRIVIA WITH SPEEDQUIZZING

Sunday, June 29 at 2 PM
Williamsburg Winery Merchants Square Tasting Room, 427 W Duke of Gloucester St
Join Matt Chambers of Speedquizzing VA for a special whiskey and wine themed afternoon of trivia! Come ready to flex your knowledge of all things beverages… the top teams will win Williamsburg Winery gift cards, and first place will be crowned the Whiskey & Wine Weekend Speedquizzing Trivia Champions! It is free to participate in the trivia and wine will be available for purchase. No tickets or reservations are required for this free event.

ONGOING:

IRISH WHISKEY TASTING SPECIAL AT DoG STREET PUB

Friday, June 27 from 11:30 AM-9:00 PM // Saturday, June 28 from 11:30 AM-9:00 PM // Sunday, June 29 from 11:30 AM-8:00 PM
401 W Duke of Gloucester Street
Throughout the weekend, the DoG Street Gastro Pub is offering an Irish whiskey tasting special, featuring Jameson’s Caskmate Line paired with their very own Maizie’s ESB, made exclusively for the restaurant by Alewerks Brewery (and named after the the dog featured in the DoG St Pub logo)! The special includes Jameson Caskmate Cold Brew, Jameson IPA Edition & Jameson Stout Edition paired with a half pint of the Alewerks Maizie’s ESB.

REVOLUTION GOLF & GRILLE WHISKEY SPECIALS

Friday & Saturday, June 27 & 28 from 11 am-10 pm // Sunday, June 29 from 11 am-9 pm
1430 High Street
Visit Revolution Golf & Grille during the weekend for lunch or dinner to order their whiskey meal specials, including maple bourbon BBQ wings, a Jack Daniel’s Burger, and a whiskey caramel bread puzzle. Wine specials are also available! Check out the weekend special menu here.

BOURBON SPECIALS AT THE PEANUT SHOP

Friday, June 27 from 10 am-7 pm // Saturday, June 28 from 9 am-7 pm // Sunday, June 29 from 10 am-6 pm
414 Prince George Street
Visit The Peanut Shop of Williamsburg for a 20% discount on everything bourbon, including whiskey grilling and barbecue sauces, jams, honey, chocolate bars, candles, and more!

FLIGHTS AT WILLIAMSBURG WINERY

Friday & Saturday, June 27 & 28 from 12-8 pm / Sunday, June 29 from 12-7 pm
Williamsburg Winery, 427 W Duke of Gloucester St
FEATURING THE “BARREL MATES” FLIGHT
Sip, swirl and unwind at the Williamsburg Winery Colonial Tasting Room with Barrel Mates – a specially curated wine flight featuring four 2 oz pours of their finest wines. Whether you’re a wine devotee or a whiskey connoisseur, this flight is a perfect pairing partner for the night. Let’s cheers to the barrels that bond us all! No reservations are required, walk-in service is available. Wines are available for tastings in flights, by the glass, or by the bottle.

FREE DISTILLERY TOURS AT COPPER FOX

Friday, Saturday, and Sunday, June, 27-29 various times
901 Capitol Landing Rd
GO BEHIND THE SCENES In honor of Copper Fox’s 20th Anniversary, the distillery is offering free tours throughout the weekend. This tour provides a behind-the-scenes glimpse of their production areas where guests will learn about distillery production and how Copper Fox makes award-winning whisky and spirits. The tour lasts approximately 45 minutes and ends in the Speakeasy tasting room where guests can enjoy tasting flights and handcrafted cocktails. For further details, please visit the Copper Fox website.

TASTING EXPERIENCE AT SILVER HAND MEADERY

Reservation slots available Friday, Saturday, and Sunday, June 27 – 29
224 Monticello Ave
FEATURING SAMPLES OF 8 MEADS & 10 HONEYS From Beowulf to Robin Hood to Game of Thrones we’ve all read about or heard of mead, but what exactly is it? In this 40 minute tasting experience you will learn all about mead, its different styles and its main ingredient, honey. Discover the differences between unique varietals of honey and how they contribute to the flavor of mead. Also learn about how different ingredients from fruit to spice to even coffee or tea impact the style and flavor of mead. Tasting includes approximately ten samples of honey and eight samples of mead.

Make a reservation online, over the phone, or as a walk-in.

SELF-GUIDED FLIGHTS & POURS AT SILVER HAND MEADERY

Friday & Saturday, June 27 & 28 from 11 am-8 pm // Sunday, June 29 from 11 am-6 pm
224 Monticello Ave
CHOOSE YOUR OWN POURS FROM A MENU OF MEADS & HONEYS
Stop by Silver Hand Meadery for a flight (4 1 oz. pours) or glass in their Tap Room during regular operating hours. Options include their standard bottled options and an experimental Mead Lab menu, as well as a self-guided honey tasting featuring ten different honeys. Walk-in service, no reservations required.

The full schedule is available at williamsburgwhiskeywine.com. Sponsored by the City of Williamsburg.