Festivals in Winchester

• Fri, 24 Apr, 2026 - 03:00 PM

  United Bank Bloomin' Wine Fest

  Downtown Walking Mall

  1094+ Interested
• Fri, 01 May, 2026 - 07:00 PM

  Trex Music Fest

  John Handley High School

  81+ Interested
• Sat, 23 May, 2026 - 11:00 AM

  Strawberry Festival

  4305 Middle Road, Winchester, VA, United States, Virginia 22602

  7632+ Interested
• Thu, 30 Apr, 2026 - 07:00 PM

  Carter Myers Automotive Jimmy Buffett Tribute Show

  James R. Wilkins, Jr. Athletic & Events Center

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

  Coronation of Queen Shenandoah

  John Handley High School

  13+ Interested
• Sat, 12 Sep, 2026 - 10:00 AM

  Sunflower Festival

  2502 N. Frederick Pike, Winchester, VA

  4959+ Interested
• Sat, 08 Aug, 2026 - 09:00 AM

  Peach Festival

  3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

  163+ Interested
• Sat, 06 Jun, 2026 - 12:00 PM

  Hop Blossom Craft Beer Festival 2026

  Old Town Winchester

  USD 7
• Sat, 03 Oct, 2026 - 11:00 AM

  Apple Harvest Festival

  4305 Middle Road, Winchester, VA, United States, Virginia 22602

  432+ Interested
• Thu, 30 Apr, 2026 - 08:00 PM

  A1A - Shenandoah Apple Blossom Festival - Winchester, VA

  Shenandoah Apple Blossom Festival®
• Sun, 14 Jun, 2026 - 12:00 PM

  NAACP Winchester Area Juneteenth 2026

  Museum of the Shenandoah Valley

  55+ Interested
• Sat, 02 May, 2026 - 01:30 PM

  Pack 46 Grand Feature Parade Seats

  Winchester

  USD 14
• Sat, 01 Aug, 2026 - 11:00 AM

  Peaches & Beaches Festival

  4305 Middle Road, Winchester, VA, United States, Virginia 22602

  350+ Interested
• Sat, 21 Mar, 2026 - 12:00 PM

  The YDC Spring Spectacular

  302 S Loudoun Street, Winchester, VA

  88+ Interested
• Sat, 09 May, 2026 - 08:00 AM

  66th Annual Apple Blossom Antique Car Meet

  Jim Barnett Park

  345+ Interested