2023 Special Events Calendar Announced!

2023, we’re ready for you!

The Main Street program of Old Town Winchester is happy to present the 2023 year-at-a-glance calendar for special events and offerings taking place in Old Town this year. See below for a full list of all currently scheduled major events and their respective sponsoring organizations, and stay tuned for more details throughout the year on additional events and details!

*NOTE: Some slight corrections have been made to this post since its initial publication. Information is correct as of 1/11/23.


  • FEBRUARY 1-28: Black History Month Art Walk [Old Town Winchester]
  • SAT FEBRUARY 4: Chocolate Escape [Old Town Winchester]
  • FEBRUARY 20-25: Restaurant Week [Winchester Main Street Foundation]
  • FRI MARCH 3: First Friday [Old Town Winchester]
  • SAT MARCH 11: Celtic Fest [Old Town Winchester]
  • FRI APRIL 7: First Friday [Old Town Winchester]
  • APRIL 28-29: Apple Blossom Bloomin’ Wine Fest [Shenandoah Apple Blossom Festival]
  • MAY 5-6: Apple Blossom Old Town Midway [Shenandoah Apple Blossom Festival]
  • FRI MAY 5: Apple Blossom Firefighters’ Parade [Shenandoah Apple Blossom Festival]
  • SAT MAY 6: Apple Blossom Grand Feature Parade [Shenandoah Apple Blossom Festival]
  • SAT MAY 11: KidzFest [Old Town Winchester]
  • FRI JUNE 2: First Friday
  • SAT JUNE 10: Hop Blossom Beer Festival [Hop Blossom]
  • FRI JUNE 16: Juneteenth Celebration [Old Town Winchester & Hood-Love]
  • JULY 1-31: Find Waldo Local Scavenger Hunt [Winchester Book Gallery]
  • MON JULY 3: Rockin’ Independence Eve [Old Town Winchester]
  • FRI JULY 7: First Friday [Old Town Winchester]
  • FRI AUGUST 4: First Friday [Old Town Winchester]
  • FRI SEPTEMBER 1: First Friday [Old Town Winchester]
  • SEPTEMBER 7-10: Skyline Indie Film Fest [Skyline Indie Film Fest]
  • SEPTEMBER 9-10: ShenArts Art Fair [Shenandoah Arts Council]
  • SAT SEPTEMBER 16: Fiddles & Fifths [Winchester EDA]
  • SAT SEPTEMBER 23: Celebración of Winchester [Winchester Main Street Foundation]
  • FRI SEPTEMBER 29: Oktoberfest [Literacy Volunteers of Winchester Area]
  • FRI OCTOBER 6: First Friday [Old Town Winchester]
  • FRI OCTOBER 20: Porches for a Purpose [Literacy Volunteers Winchester Area]
  • THU NOVEMBER 2: Día de los Muertos [Old Town Winchester & Arte Libre VA]
  • FRI NOVEMBER 3: First Friday [Old Town Winchester]
  • NOVEMBER 24-26: Windependent Weekend [Old Town Winchester]
  • SAT DECEMBER 9: Holiday Open House & Winter Market [Old Town Winchester]
  • SUN DECEMBER 31: NYE Apple Drop [Old Town Winchester]
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