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 2019

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Calendar of Events

Calendar of Events
Sunday Monday Tuesday Wednesday Thursday Friday Saturday

aMuse Art & Craft Festival

Loudoun Street Mile

Memorial Day Observance

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Pride Drag Show

Strawberry Festival

Winchester Craft Beer Week

Garden Fest

Old Town Farmers Market

Winchester Wings & Wheels

Winchester Craft Beer Week

Winchester Craft Beer Week

Winchester Craft Beer Week

Winchester Craft Beer Week

Winchester Craft Beer Week

Outdoor Movie Series: Smallfoot

Winchester Craft Beer Week

Hop Blossom Craft Beer Festival

Old Town Farmers Market

Military History Day – 75th Anniversary of D-Day Invasion

Sightseeing Express Trolley Tour

Pottery Show and Sale

Military History Day – 75th Anniversary of D-Day Invasion

Pottery Show and Sale

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Second Battle of Winchester Anniversary

Outdoor Movie Series: Spider-Man: Into the Spider Verse

Spottswood Poles Night at Bridgeforth Field

Gardens at Night: The Robbie Limon Band

History and Civil War Walking Tour

History at Sunset

Theatre for Kids: Robin Hood

Kids Civil War History Camp

Old Town Farmers Market

History and Civil War Walking Tour

Middletown Heritage Day

Theatre for Kids: Robin Hood

Theatre for Kids: Robin Hood

International Willa Cather Seminar

Juneteenth Presentation

Theatre for Kids: Robin Hood

International Willa Cather Seminar

Theatre for Kids: Robin Hood

International Willa Cather Seminar

Curves to Cores HOG Motorcycle Rally

Limited Time Exhibit: Patsy Cline Style in Leather

Theatre for Kids: Robin Hood

International Willa Cather Seminar

Curves to Cores HOG Motorcycle Rally

Limited Time Exhibit: Patsy Cline Style in Leather

Sunset Series on the Garden Rooftop

Theatre for Kids: Robin Hood

International Willa Cather Seminar

Curves to Cores HOG Motorcycle Rally

Limited Time Exhibit: Patsy Cline Style in Leather

Friday Night Live

Theatre for Kids: Robin Hood

Curves to Cores HOG Motorcycle Rally

Limited Time Exhibit: Patsy Cline Style in Leather

Old Town Farmers Market

New Orleans Festival

Limited Time Exhibit: Patsy Cline Style in Leather

Rebecca and Thomas: A Civil War Spy Tale

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Music Theatre: Ragtime

Outdoor Movie Series: Lego Movie 2: The Second Part

Music Theatre: Ragtime

History at Sunset

Music Theatre: Ragtime

Old Town Farmers Market

Trails Tour

Pride Celebration

Music Theatre: Ragtime

Music Theatre: Ragtime

Music Theatre: Ragtime

Rockin’ Independence Eve

Music Theatre: Ragtime

Fourth of July Celebration and Parade

Fourth of July Celebration

Music Theatre: Ragtime

“Hog Wild in Winchester” – A whimsical play

Music Theatre: Ragtime

Little Red and Ryding Hood: A Benefit Exhibition

Music Theatre: Ragtime

Scottish Highland Games

Old Town Farmers Market

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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.