Entertainment events in Winchester

• Thu, 30 Apr, 2026 - 07:00 PM

  Carter Myers Automotive Jimmy Buffett Tribute Show

  James R. Wilkins, Jr. Athletic & Events Center

  98+ Interested
• Fri, 01 May, 2026 - 11:00 AM

  First Bank Men's Commonwealth Luncheon

  Piccadilly's Public House and Restaurant

  6+ Interested
• Sun, 07 Jun, 2026 - 07:30 PM

  Nitty Gritty Dirt Band at The Monument

  The Monument
• Thu, 30 Apr, 2026 - 08:00 PM

  A1A - Shenandoah Apple Blossom Festival - Winchester, VA

  Shenandoah Apple Blossom Festival®
• Fri, 27 Mar, 2026 - 08:00 PM

  The Travelin McCourys at Backseat Events

  Backseat Events
• Sat, 02 May, 2026 - 05:00 PM

  Graham Barham in Winchester

  James R. Wilkins
• Sat, 18 Apr, 2026 - 11:00 AM

  New Playground Grand Opening Event

  Winchester VA Parks and Recreation

  749+ Interested
• Wed, 29 Apr, 2026 - 06:00 PM

  Navy Federal Credit Union Veterans Dinner Show

  James R. Wilkins, Jr. Athletic & Events Center

  37+ Interested
• Sat, 21 Mar, 2026 - 05:00 PM

  Cash Party

  250 Costello Dr, Winchester, VA 22602-4310, United States

  381+ Interested
• Mon, 27 Apr, 2026 - 06:30 PM

  Ballerina Nail & Spa Pumps and Pearls Ladies Party

  Bright Box (Winchester, VA)

  36+ Interested
• Fri, 01 May, 2026 - 08:30 PM

  Queen's Ball and Dance Party

  1300 Senseny Rd, Winchester, VA 22602-6418, United States

  11+ Interested
• Sat, 21 Mar, 2026 - 07:00 PM

  Comedy Night at James Charles Winery

  4063 Middle Rd, Winchester, VA, United States, Virginia 22602

  86+ Interested
• Fri, 01 May, 2026 - 07:00 PM

  The All Access Dance Party | Apple Blossom Festival Weekend

  Backseat Events USA

  USD 18
• Fri, 15 May, 2026 - 08:00 PM

  Micro Wrestling: Winchester, VA!

  Backseat Events

  45+ Interested
• Sat, 02 May, 2026 - 08:00 PM

  The Amish Outlaws at Backseat Events

  Backseat Events