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 June 2021

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Calendar of Events

Calendar of Events
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Healing Field of Honor

Healing Field of Honor

Loudoun Street Mile

Memorial Day at Valerie Hill

Middletown Memorial Day Service


History and Civil War Walking Tour


Cedar Creek Battlefield Museum Grand Opening

Clowser Foundation Memorial Service

The Pink Picnic

Movie and Drag Show Brunch


Winchester Royals Baseball Opening Night


Rotary Rummage Sale

Yeti Sun Run

Second Battle of Winchester Anniversary

Willow Moon Farm Greenhouse Grand Opening

Military History Day

Rotary Rummage Sale

Yeti Sun Run

Second Battle of Winchester Anniversary

David Andrew Smith Live at Briede Vineyards


Family Day Fishing Rodeo

“Type Your Story” Type In

African American Civil War Trails Marker Unveiling

Music, Moons, and Magic Balloons


Teens Inc. Farmers Market

The Little Mermaid

Winchester Arts & Music Festival

Raised on Analog Live at West Oaks

The Little Mermaid

Winchester Arts & Music Festival

Guided Civil War Walking Tour of Stephens City

Winchester Arts & Music Festival


Newcomers Welcome Event

History and Civil War Walking Tour

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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.