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.

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Events for August 2021

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Calendar of Events

Calendar of Events
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Summer Music Theatre: Grease


Morning Garden Walk


The Final Yard Quilt Fair

History and Civil War Walking Tour

Plays on the Dock Scripts Festival

The Final Yard Quilt Fair

Iris Sale

West Oaks Peach Festival

Swim Under the Stars


Voices of the Shenandoah – Prince Bellerose in Concert

Gardens at Night: Groove Train

Plays on the Dock Scripts Festival

Winchester Greek Festival

Route 11 Yard Crawl

Marker-Miller Peach Festival

Winchester Greek Festival

Route 11 Yard Crawl

Middletown’s Annual Car, Truck, & Tractor Show

Richard’s Peach Festival


Quilt Show


CCAP Benefit Bike Tour

Guided Civil War Walking Tour of Stephens City

Belle Grove Wine Fest

Blanc on Blanc Wine Dinner


Spice Workshop with Natalie Ramos

Core of the Community Festival: Concern Hotline Fish Fry

History and Civil War Walking Tour

Core of the Community Festival: Shenandoah Apple Blossom Festival® Inc. BBQ & Brews

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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.