All Upcoming events

• Sat, 14 Mar, 2026 - 12:00 PM

  Celtic Fest

  Old Town Winchester

  1004+ Interested
• Fri, 01 May, 2026 - 09:00 PM

  Claudio’s Pizzeria Friday Night Fever Disco Dance Party

  James R. Wilkins, Jr. Athletic & Events Center

  94+ Interested
• Fri, 24 Apr, 2026 - 12:00 PM

  HoneyWay Apple Blossom Golf Classic

  Rock Harbor Golf Course

  4+ Interested
• Sun, 29 Mar, 2026 - 12:00 PM

  West Oaks 7th Annual Adult Egg Hunt

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

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

  Carter Myers Automotive Jimmy Buffett Tribute Show

  James R. Wilkins, Jr. Athletic & Events Center

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

  Strawberry Festival

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

  5029+ Interested
• Fri, 01 May, 2026 - 01:30 PM

  Coronation of Queen Shenandoah

  John Handley High School
• Fri, 20 Mar, 2026 - 06:30 PM

  Flashlight Egg Hunt

  1001 E Cork St, Winchester, VA, United States, Virginia 22601

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

  First Bank Men's Commonwealth Luncheon

  Piccadilly's Public House and Restaurant
• Fri, 06 Mar, 2026 - 07:00 PM

  Country Nite @ Bright Box Theater in Winchester, VA

  Bright Box Theater

  USD 18
• Sat, 12 Sep, 2026 - 10:00 AM

  Sunflower Festival

  2502 N. Frederick Pike, Winchester, VA

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

  Apple Harvest Festival

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

  375+ 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
• Thu, 09 Apr, 2026 - 08:00 PM

  Jackyl in Winchester

  Backseat Events
• Sat, 01 Aug, 2026 - 11:00 AM

  Peaches & Beaches Festival

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

  259+ Interested
• Fri, 27 Feb, 2026 - 08:00 PM

  An Evening with Stephane Wrembel

  Bright Box (Winchester, VA)

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

  Hop Blossom Craft Beer Festival 2026

  Old Town Winchester

  USD 7
• Sat, 28 Feb, 2026 - 10:00 AM

  32nd Annual Valley Health Community Wellness Festival

  Apple Blossom Mall

  105+ Interested
• Sat, 04 Apr, 2026 - 09:00 AM

  West Oaks Spring Vendor Fair 2026

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

  560+ Interested
• Wed, 18 Mar, 2026 - 04:30 PM

  Rhea Lana's of Winchester Spring/Summer Family Shopping Event!

  221 Commonwealth Ct, Winchester, VA 22602, USA

  557+ Interested
• Sat, 21 Mar, 2026 - 08:00 PM

  For Whom the Bell Tolls: The Four Horsemen

  114 Full House Drive , Winchester, VA, United States, Virginia 22603
• Sat, 31 Oct, 2026 - 10:00 AM

  Samhain Luna Market 2026

  125 S. Loudoun Street, Winchester, VA

  65+ Interested
• Fri, 17 Apr, 2026 - 07:00 PM

  Tracy Byrd in Winchester
• Sat, 18 Apr, 2026 - 11:00 AM

  New Playground Grand Opening Event

  Winchester VA Parks and Recreation

  507+ Interested
• Sat, 18 Apr, 2026 - 08:30 PM

  90s & 00s Night @ Backseat Bar & Grill

  Backseat Bar and Grill

  184+ Interested
• Sun, 22 Mar, 2026 - 12:00 PM

  Spring Bridal Expo 2026

  The George Washington Hotel

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

  66th Annual Apple Blossom Antique Car Meet

  Jim Barnett Park

  249+ Interested
• Wed, 18 Mar, 2026 - 04:00 PM

  Little Chefs Sauce Lab at Chick-fil-A

  Chick-fil-A Pleasant Valley Road (2230 S Pleasant Valley Rd, )
• Sat, 29 Aug, 2026 - 11:00 AM

  Pickle-chester

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

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

  Kids Festival

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

  403+ Interested
• Fri, 13 Mar, 2026 - 06:00 PM

  🍀🎻 Saint Patrick’s Party at West Oaks! 🎻🍀

  4305 Middle Road, Winchester, VA, United States, Virginia 22602
• Thu, 09 Apr, 2026 - 08:00 PM

  Jackyl — Chainsaws, Southern Rock and Loud Guitars

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

  112+ Interested
• Wed, 29 Apr, 2026 - 11:00 AM

  Valley Health Business at the Bloom

  James R. Wilkins, Jr. Athletic & Events Center

  27+ 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
• Sat, 11 Apr, 2026 - 08:00 PM

  Backseat Rocks with That Arena Rock Show

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

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

  McDonald's Apple Blossom Gaming Festival

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

  12+ Interested
• Fri, 01 May, 2026 - 11:45 AM

  Valley Cycle Center Stag Luncheon

  Winchester Cold Storage / WCS Logistics

  9+ Interested
• Sat, 18 Apr, 2026 - 12:00 PM

  Ambrogi Acres 2nd Annual 420 Event

  Backseat Events

  328+ Interested
• Sat, 14 Mar, 2026 - 10:00 AM

  Glazed and Confused

  27 North Loudoun Street, Winchester, VA, United States, Virginia 22601
• Fri, 05 Jun, 2026 - 05:00 PM

  First Friday

  Old Town Winchester
• Sat, 09 May, 2026 - 09:00 AM

  Bright Box Card Bazaar: An Indoor Pokemon Vendor Show

  Bright Box (Winchester, VA)

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

  Miss Honorary Fire Chief Contest

  James Wood Middle School

  10+ Interested
• Sat, 04 Apr, 2026 - 09:00 AM

  West Oaks Farm Market's 2026 Spring Vendor Fair

  West Oaks Farm Market
• Sat, 28 Feb, 2026 - 11:00 AM

  Guest Reading: Mad Hatter Tarot

  125 S. Loudoun Street, Winchester, VA

  4+ Interested