Winchester VA Events Calendar

Just a short day trip from Washington, DC and the Northern Virginia area, Winchester VA events provide affordable, year-round entertainment for the whole family. From museum exhibits to guided tours, concerts, parades, live theater, fireworks displays, fall festivals, and live entertainment, there is so much to discover in Winchester, Virginia.

PLEASE NOTE: Due to numerous cancellations of large gatherings due to COVID-19, these events are subject to change. Please call ahead to confirm that an event is still being held.

Loading Events

Events for September 2020

Events Search and Views Navigation

Event Views Navigation

Calendar of Events

Calendar of Events
Sunday Monday Tuesday Wednesday Thursday Friday Saturday

Friday Fish Fry Celebration

Raptor Hill Falconry


Skyline Indie Film Fest

Skyline Indie Film Fest

Skyline Indie Film Fest

Skyline Indie Film Fest

Abby the Spoon Lady


Shenandoah Valley Apple Harvest Festival

Third Winchester Living History Programs

Classic Cars Under the Stars

Shenandoah Valley Apple Harvest Festival


Melanie Pearl Music

Artisans Jubilee Craft Fair

Fall Greek Takeout Event

Rocky Horror Picture Show at the Drive-In

Rocky Horror Picture Show at the Drive-In

Tomato Festival


Hocus Pocus and Little Shop of Horrors at the Drive-In

Free First Friday

Chuggalug Live at West Oaks

Hocus Pocus and Little Shop of Horrors at the Drive-In

Trainwreck Live on the Boat

+ Export Events

Annual Winchester VA Events and Festivals

The Shenandoah Apple Blossom Festival has been the signature Winchester VA Event in the region for over 90 years! This festival, also called “The Bloom,” is awinchester va events, apple blossom festival, winchester, things to do in winchester, virginia series of over forty events spanning 10 days. For more information, visit

The Winchester region has long been known for its farm markets and apple orchards, so naturally, our calendar is packed with fall festivals celebrating apples, pumpkins, and more! Plan your trip around one of these annual Winchester, VA events.

Other popular annual Winchester events include Hop Blossom Craft Beer Festival, 4th of July Celebrations, Route 11 Yard Crawl, Frederick County Fair, Apple Harvest Festivals, Walking in a Winter Wonderland holiday light display, and the family-friendly First Night Winchester celebration on New Year’s Eve.

Arts, History, and Old Fashioned Fun

Shenandoah Conservatory, winchester va events, things to do in winchester, virginiaThe performing arts scene in the Winchester community is incredibly vibrant. Shenandoah University’s Conservatory hosts events featuring both students and world-renowned performers in dance, music, opera, symphony orchestra, theatre, and more. Shenandoah Summer Music Theatre also produces several Broadway musicals every summer.

If you are interested in history, check out our annual Civil War Weekend and African American History Day. We have numerous educational programs and tours at our museums, battlefields, and historic sites too.

We are also home to the only drive-in theater in the DC Metro area! The retro 1956 Family Drive-In Theatre not only shows double features but also hosts family-friendly events just south of Winchester in Stephens City.