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.
LIST OF EVENTS
- 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]