BIZ BRIEF: Williamsburg’s Whiskey & Wine Weekend Pours Business Into Local Economy
Annual summer event gives visitors and locals a shot to explore unique libations
WILLIAMSBURG, VA — With the return of Williamsburg Whiskey & Wine Weekend from June 27–29, 2025, the city is once again raising a glass to the powerful intersection of tourism and economic development. The annual event—billed as a “premier summer celebration” in the heart of historic Williamsburg—is more than a showcase of spirits and culture. For local businesses, it’s a significant source of revenue, exposure, and long-term customer growth.
The event is produced by AVAdventure Productions, a key creative partner for the City of Williamsburg. Known for staging community-focused festivals, AVAdventure also produces events like the Last Word Comedy Festival, the Ampersand International Arts Festival, BurgQuest, and the Virginia Cat Festival.
The weekend centers around the Williamsburg Whiskey & Wine Pass, a digital ticket that gives attendees access to tastings, classes, and exclusive promotions. Guests can check in at participating locations to earn rewards like a commemorative glass—an incentive that encourages exploration across the city.
“Experiential events like Williamsburg Whiskey & Wine Weekend attract new visitors to the area, which helps bring a positive boost to our local economy,” said Edward Harris, Chief Executive Officer of Visit Williamsburg. “New event development has become a priority in the tourism industry for leading destinations. Hotels, restaurants, retail shops, breweries, wineries, distilleries and many other attractions will continue to benefit from events, as they give potential visitors additional reasons to discover or re-discover our unique destination.”
The organizers of Whiskey & Wine Weekend have curated a robust itinerary of tastings, entertainment, and retail promotions designed to drive foot traffic and revenue for local establishments. Last year’s event boosted business sales by over 40%, a figure that participating venues hope to match or exceed this year.
Among the participating venues, The Williamsburg Winery will offer its signature “Barrel Mates” flight all weekend at its Merchants Square location, along with a lively trivia contest on Sunday afternoon where guests can test their beverage knowledge and win prizes.
Just across town, Copper Fox Distillery will mark its 20th anniversary with two full days of celebration. Saturday’s events include Cousins Maine Lobster and live music from the CK Band, while Sunday brings Moto Crepes and classic jazz from The Generations Trio. Free distillery tours and Speakeasy tastings will run all weekend.
Silver Hand Meadery is offering multiple tasting experiences at its Monticello Avenue location. Guests there will sample ten types of honey and eight meads while learning about the history and styles of the ancient beverage.
The city’s restaurants are also tapping into the momentum. Blue Talon Bistro will host a guided Pinot Noir tasting on Friday evening, led by wine expert Matt Earnhardt, with international selections and small bites available for a $25 ticket. Meanwhile, Dog Street Pub is showcasing its “Maizie Meets Jameson” pairing, combining Jameson’s Caskmate whiskeys with a custom brew made in partnership with Alewerks.
At Revolution Golf & Grille, guests can enjoy whiskey-infused menu items including maple bourbon BBQ wings, a Jack Daniel’s burger, and whiskey caramel bread pudding, available all weekend.
Even Illy Caffé is joining the celebration with a creative twist. On Saturday night, the European-style coffee shop will transform into an after-hours comedy club, offering a free “Cocktails & Comedy” event featuring touring stand-up comedians. Seating is first-come, first-served, with food and drinks available for purchase.
Retailers are also playing a key role in the experience. Three Sisters Boutique will host complimentary wine tastings on Friday and Saturday featuring their 2021 Southern Belle “Precious” Syrah, aged in Pappy Van Winkle bourbon barrels. Attendees can also enjoy a 10% discount on all in-stock wine.
At Brick & Vine, the official Colonial Williamsburg store, visitors can join in mead tastings hosted by Silver Hand Meadery from 2:00–4:00 PM both Friday and Saturday. The Peanut Shop, another local favorite, will offer 20% off all bourbon-themed items throughout the weekend, from whiskey barbecue sauces to specialty chocolates.
With its blend of Southern charm, live music, curated drinks, and exclusive deals, the Williamsburg Whiskey & Wine Weekend has proven to be a win-win: an enriching experience for guests and a measurable success for local businesses. As the city continues investing in events that fuel tourism and cultural engagement, stakeholders across Williamsburg are toasting a growing future—one glass at a time.
A Williamsburg Independent Contributor used AI for this post.