Author
Reginald Leonard II
Co-Founder of Oenoverse & Steering Committee Member, Discover Black Cville
Everything You Need to Know About Two Up Wine Down in Charlottesville
Written by Reginald Leonard II, Co-Founder of Oenoverse & Steering Committee Member, Discover Black Cville
More than a traditional tasting event, Two Up Wine Down brings together curated pours, live music, local food, and conversations that highlight the diversity and creativity shaping Virginia wine today.
Whether you're planning your first visit to Charlottesville or looking for a new annual tradition, here's why Two Up Wine Down deserves a spot on your fall itinerary.
-- 2026 Update --
Details for Two Up Wine Down are still being finalized for 2026! Save the date for November 7th, 2026 at the Jefferson School City Center, and read on for a peak at what 2025's festival had to offer! It's going to be a vibe you don't want to miss.
A Unique Wine Fest
What makes Two Up Wine Down different from most wine festivals is the curator model. Every bottle you taste is personally selected by the person pouring it, whether that's a sommelier, a wine educator, a winemaker, or an enthusiast who's been putting in work in Virginia wine country. We’ll have food from local vendors Rum Punch, Vegan Comfort Soul, and Popitos Pizza. DJ Nobe handles the music, leaning heavy into hip hop and R&B, and by the second hour the whole thing tends to turn into a dance party on the lawn. The crowd is multigenerational, people fly in from around the country for it, and the vibe is less "wine tasting" and more "a wine kickback with your crew."
A Full Weekend of Events
This year the festival continues the trend of leaning into a full weekend of events:
-- Friday night opens with “Deconstructed” at Ethos Wine & Tea Bar, featuring “The Dapper Oenophile” from the DMV and Randi from Diversified Vines (coming in from Atlanta) for an evening of exclusive pours and wine-and-music pairings. Tickets are still available but moving fast, and there likely won’t be any at the door.
-- Saturday morning, Wayne from Wild Big Camp is leading a beginner-friendly historical hike at James Monroe’s Highland. It’s free, but you’ll need to RSVP.
-- Then the main festival runs from 2-5 pm, with a VIP hour kicking off at 1 pm. (VIP is sold out at the moment, but it’s worth flagging for next year if you want early access and exclusive bottles.)
This Year's Highlights
One of this year's highlights is Cha McCoy, the New York-based sommelier whose book Wine Pairing for the People just dropped this week. She'll be at the festival signing copies and holding court, which alone is worth the price of admission if you've been following her work. Beyond that, expect the usual suspects: curators pouring their selections, food available for purchase, and the option to buy bottles of whatever you're feeling to take home or enjoy on site. The weekend wraps with an official after party at Ethos, which is also ticketed and highly recommended and will definitely sell out.
Make Your Plans
TUWD happens annually around late October or early November, with dates announced each early that year. If this year doesn't work for you, start penciling in next November now. If you're around, grab your festival tickets, secure Deconstructed, RSVP for the hike, and lock in those after party tickets.
Find full details at twoupwinedown.com
And of course, there's so much more happening in Charlottesville and Albemarle County, especially in the fall! One blog couldn’t possibly capture everything that’s happening, so head over to our upcoming events page to stay up to date on all the latest happenings in the area!