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

  90+ Interested
• Sat, 28 Feb, 2026 - 08:00 PM

  Shades of HUNKS at Winchester Brew Works (Winchester, VA) 02/28/26

  Winchester Brew Works

  USD 18
• Sat, 18 Apr, 2026 - 11:00 AM

  New Playground Grand Opening Event

  Winchester VA Parks and Recreation

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

  Navy Federal Credit Union Veterans Dinner Show

  James R. Wilkins, Jr. Athletic & Events Center

  30+ Interested
• Sat, 14 Mar, 2026 - 05:00 PM

  Cash Party

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

  361+ 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

  20+ Interested
• Thu, 26 Mar, 2026 - 08:00 PM

  5AM Trio: Esoterra Tour

  Bright Box Theater

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

  Comedy Night at James Charles Winery

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

  35+ Interested
• Thu, 26 Mar, 2026 - 07:30 PM

  Our Town

  Glaize Studio Theatre
• Fri, 08 May, 2026 - 08:00 PM

  30 Years of The Reagan Years!

  114 Full House Drive , Winchester, VA, United States, Virginia 22603

  49+ Interested
• Wed, 08 Apr, 2026 - 07:30 PM

  90's Nickelodeon Trivia @ DCBC!

  160 N Loudoun St, Winchester, VA, United States, Virginia 22601

  13+ Interested
• Sat, 07 Mar, 2026 - 08:00 PM

  The Lucky Brew Works Drag Show!

  320 N Cameron St, Winchester, VA

  68+ Interested
• Wed, 04 Mar, 2026 - 07:00 PM

  Harlem Globetrotters 2026 - 100 Year Tour - Winchester, VA

  James R. Wilkins, Jr. Athletics & Events Center

  USD 32
• Wed, 25 Feb, 2026 - 07:30 PM

  Trivia @ DCBC: I <3 the 90's!

  160 N Loudoun St, Winchester, VA, United States, Virginia 22601

  49+ Interested