Two Up Wine Down isn’t your typical wine festival. Virginia wine, curated pours, music, food, and a crowd that's there to have a good time... Two Up Wine Down brings a different energy to the Virginia wine festival scene.
Held annually in Charlottesville, Two Up Wine Down feels less like a traditional tasting event and more like a really good wine kickback with your crew.
And while the festival happens once a year, the idea behind it is much bigger. Here’s what to know before you go.
Two Up Wine Down is an annual Virginia wine festival created by Oenoverse and The Veraison Project, two organizations working to expand access, opportunity, and participation in Virginia's wine industry.
The festival was created around a simple idea: Virginia wine can be serious without being intimidating. Instead of making wine knowledge the price of admission, Two Up Wine Down invites guests to come curious. Experienced wine drinkers can discover new producers and perspectives, while newcomers can taste Virginia wine in a relaxed setting without feeling like they need to know the difference between every grape variety before they arrive.
Even the name is distinctly Virginia. “Two Up” references the Commonwealth’s unofficial hand sign -- two fingers up for the V and two down for the A, while “Wine Down” captures the laid-back spirit of the festival. At its heart, Two Up Wine Down is about bringing people together and showing them there isn’t one right way to experience Virginia wine.
The signature feature of Two Up Wine Down is its curator model.
Rather than simply moving from winery table to winery table, guests meet wine curators who select the Virginia wines they want to share. Past curators have included sommeliers, wine educators, writers, winemakers, and passionate wine enthusiasts from Virginia and beyond. That means the person pouring your wine isn’t just pouring a bottle -- they can tell you why they chose it, introduce you to the producer, and share the story or perspective behind the bottle. The result is a tasting experience built around conversation, storytelling, and discovery.
Expect Virginia wine, but don’t expect a quiet afternoon of standing around tasting tables.
Two Up Wine Down is intentionally social. Guests can expect to spend the event moving between wine curators and local food vendors. Music is also a major part of the festival, with hip-hop and R&B setting the tone for conversation and dance. Have you ever done the wobble while wine tasting? Two Up Wine Down will change that! You might arrive looking for a favorite Virginia wine and leave with a new producer on your list, or you might arrive knowing very little about Virginia wine and find a bottle (or a person) that makes you want to learn more. Either way, you don't need to be a wine expert to enjoy the festival.
VIP experiences add another layer to the festival, typically offering a more intimate setting, special wines, and additional opportunities to connect with the people behind the event.
Two Up Wine Down takes place annually in Charlottesville, Virginia, generally in the fall.
2026 Festival Date: Saturday, November 7, 2026
Location: Jefferson School City Center. The festival is held outdoors, rain or shine, with portions of the event tented.
Main Festival: 2–5PM (VIP experiences begin at 1PM)
Festival Schedule & Tickets: Because dates, ticket options, vendors, and programming can change from year to year, check the official Two Up Wine Down website when planning your visit. Tickets are generally available online in early October.
In 2026, the fifth anniversary of Two Up Wine Down expands the celebration beyond Saturday, beginning with a special Thursday evening experience in Virginia wine country.
The 2026 weekend begins at Barboursville Vineyards with Ridge to Root, a special dinner bringing together Barboursville and the Edna Lewis Foundation for an evening of Virginia wine, food, history and storytelling. The timing is especially meaningful: 2026 marks both the 50th anniversary of Barboursville Vineyards and the 50th anniversary of the publication of Edna Lewis’s landmark The Taste of Country Cooking.
Guests can expect a family-style dinner, Virginia wine and storytelling celebrating the people, food and place behind these two Virginia legacies. Proceeds from the evening will support the Edna Lewis Foundation’s programming and scholarship efforts.
The main event takes place Saturday afternoon on the lawn at Jefferson School City Center.
Virginia wineries and guest wine curators will come together alongside local food vendors, music and wine lovers for the festival that started it all. Expect Virginia wines selected by guest curators, food vendors, DJ-spun music, and a crowd ready to spend the afternoon together. The 2026 festival's food vendors include Chimm, Vegan Comforts Soul Food, and Pearl Island, though vendors are subject to change. DJ Nobé is also returning for 2026.
Two Up Wine Down makes an easy centerpiece for a fall weekend in Charlottesville. Downtown Charlottesville offers restaurants, shops, cultural attractions and hotels within easy reach of the festival, while the surrounding Monticello Wine Trail makes it easy to add winery visits before or after the festival.
November is also a beautiful time to experience Charlottesville at a slower pace. Catch the last of the fall foliage, explore historic sites, or enjoy seasonal menus at local restaurants.
For visitors coming from Washington, D.C. or beyond, the celebration is also accessible by Amtrak, with the Charlottesville station located less than a mile away from several hotels, restaurants, and the Two Up Wine Down festival itself. Browse local places to stay and start planning your trip now.
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