Festivals in Winchester

• Thu, 30 Apr, 2026 - 07:00 PM

  Carter Myers Automotive Jimmy Buffett Tribute Show

  James R. Wilkins, Jr. Athletic & Events Center

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

  Strawberry Festival

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

  2266+ Interested
• Sat, 03 Oct, 2026 - 11:00 AM

  Apple Harvest Festival

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

  239+ Interested
• Sat, 01 Aug, 2026 - 11:00 AM

  Peaches & Beaches Festival

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

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

  66th Annual Apple Blossom Antique Car Meet

  Jim Barnett Park

  93+ Interested
• Sat, 27 Jun, 2026 - 11:00 AM

  Kids Festival

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

  217+ Interested
• Mon, 26 Jan, 2026 - 07:00 AM

  FredCo Eats Restaurant Week 2026

  Various Locations Across Frederick County, Virginia
• Sat, 29 Aug, 2026 - 11:00 AM

  Pickle-chester

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

  135+ Interested
• Sat, 17 Oct, 2026 - 11:00 AM

  Fall Harvest Festival

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

  107+ Interested
• Sat, 28 Feb, 2026 - 12:00 PM

  Paella Day

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

  7+ Interested
• Sat, 14 Mar, 2026 - 07:00 PM

  Miss Honorary Fire Chief Contest

  James Wood Middle School

  8+ Interested
• Sat, 31 Jan, 2026 - 11:00 AM

  Guest Reading: Kindred Roots Tarot

  125 S. Loudoun Street, Winchester, VA

  6+ Interested
• Sun, 03 May, 2026 - 07:00 PM

  Live Dead & Brothers: An All-Star Celebration of Grateful Dead & Allman Brothers

  Bright Box Theater

  21+ Interested
• Sun, 03 May, 2026 - 10:00 AM

  Beltane Magic Market

  105 Millwood Ave, Winchester, VA, United States, Virginia 22601

  84+ Interested
• Sat, 21 Mar, 2026 - 09:00 AM

  6th Annual Nitro Spring Fling

  246 Sulky Dr., Winchester, VA, United States, Virginia 22602

  92+ Interested