05/20/2026
What’s Happening Wednesday | Charlottesville Area (5/20–5/26) 👇
Memorial Day weekend is bringing some classic Charlottesville-area spring traditions, outdoor events, and family-friendly fun:
🎶 Scottsville Fridays on the Canal
📍 Canal Basin Square – Scottsville
📅 Friday, May 22
⏰ 5:00–8:00 PM
A great small-town Friday night setup with live music, food vendors, local drinks, and relaxing vibes along the historic canal.
🎨 Charlottesville Arts Festival
📍 IX Art Park
📅 Saturday, May 23 | 3:00–8:00 PM
📅 Sunday, May 24 | 10:00 AM–5:00 PM
Artists, live music, interactive workshops, food, and creative energy all weekend long at one of Charlottesville’s coolest venues.
🐎 King Family Polo Matches Begin
📍 King Family Vineyards
📅 Sunday, May 24
⏰ Matches at 12:00 PM & 2:00 PM
One of the area’s favorite summer traditions officially returns. Bring chairs, pack a picnic, enjoy wine, and spend the afternoon watching polo in the mountains. Matches continue every Sunday through November 1.
🐶 Batesminster Dog Show
📍 Batesville Market
📅 Sunday, May 24
⏰ 11:30 AM
A lighthearted community dog show celebrating our furry friends with plenty of laughs, local charm, and small-town energy.
☀️ Peak Patio + Winery Weekend
Memorial Day weekend always feels like the unofficial kickoff to summer around Charlottesville — expect packed wineries, patios, breweries, and lots happening all across the area.
Quick Take:
This week has a little bit of everything — art festivals, live music, polo, wine country afternoons, and one very important dog show.