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 2019

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Calendar of Events

Calendar of Events
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Music Theatre: The Sound of Music

Yer a Wizard Day

Talk on the Archaeology at Belle Grove Enslaved Quarter Site

SSMT 2019 Downtown Cabaret Series

Frederick County Fair

Music Theatre: The Sound of Music

Frederick County Fair

Music Theatre: The Sound of Music

Frederick County Fair

Music Theatre: The Sound of Music

Frederick County Fair

Music Theatre: The Sound of Music

Frederick County Fair

Music Theatre: The Sound of Music

History at Sunset

Outdoor Movie at the Amphitheater

Frederick County Fair

Music Theatre: The Sound of Music

Old Town Farmers Market

Shenandoah Valley Battlefields Foundation Conference

Music Theatre: The Sound of Music

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Winchester Salsa Night (Lessons Included)

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Route 11 Yard Crawl

History and Civil War Walking Tour

Gardens at Night: The Return

Route 11 Yard Crawl

Marker-Miller Peach Festival

Old Town Farmers Market

National Park Service Star Gazing Party

Classic Movie Night

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Winchester Salsa Night (Lessons Included)

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Civil War Weekend

Comedy Weekend

Friday Night Live

Civil War Weekend

Comedy Weekend

Winchester Greek Festival

Old Town Farmers Market

History and Civil War Walking Tour

Civil War Weekend

Winchester Greek Festival

Middletown’s 9th Annual Car, Truck, & Tractor Show

Richard’s Peach Festival

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Winchester Salsa Night (Lessons Included)

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Old Town Farmers Market

WOFM Summer Harvest Festival and Vendor Fair

Civil War History Trolley Tour

Guided Civil War Walking Tour of Stephens City

Belle Grove Wine Fest

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Free Family Fun Event

Winchester Salsa Night (Lessons Included)

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Labor Day Movie Marathon at Drive-In

From Farm to Film: An Evening with the Filmmakers

Labor Day Movie Marathon at Drive-In

Old Town Farmers Market

Civil War sign dedication

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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 thebloom.com.

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.