Festivals in Winchester

• Sat, 14 Mar, 2026 - 12:00 PM

  Celtic Fest

  Old Town Winchester

  217+ Interested
• Sat, 07 Feb, 2026 - 02:00 PM

  Chocolate Escape

  Old Town Winchester Walking Mall

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

  Strawberry Festival

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

  3532+ Interested
• Thu, 30 Apr, 2026 - 07:00 PM

  Carter Myers Automotive Jimmy Buffett Tribute Show

  James R. Wilkins, Jr. Athletic & Events Center

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

  Apple Harvest Festival

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

  323+ Interested
• Sat, 31 Oct, 2026 - 10:00 AM

  Samhain Luna Market 2026

  125 S. Loudoun Street, Winchester, VA

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

  Peaches & Beaches Festival

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

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

  66th Annual Apple Blossom Antique Car Meet

  Jim Barnett Park

  104+ Interested
• Sat, 29 Aug, 2026 - 11:00 AM

  Pickle-chester

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

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

  Kids Festival

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

  322+ Interested
• Sat, 25 Apr, 2026 - 10:00 AM

  McDonald's Apple Blossom Gaming Festival

  608 Millwood Ave, Winchester, VA 22601-5167, United States

  8+ Interested
• Sat, 04 Apr, 2026 - 11:00 AM

  Guest Reading: Kindred Roots Tarot

  125 S. Loudoun Street, Winchester, VA

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

  The All Access Dance Party | Apple Blossom Festival Weekend

  Backseat Events USA

  USD 18
• Sat, 17 Oct, 2026 - 11:00 AM

  Fall Harvest Festival

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

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

  Paella Day

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

  12+ Interested