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 May 2019

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Calendar of Events

Calendar of Events
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The 92nd Shenandoah Apple Blossom Festival

Così fan tutte

Civil War Historical Impressions

Apple Blossom Festival: Winchester Ciderworks Tasting and Orchard Tours

Apple Blossom Afternoon Tea

The 92nd Shenandoah Apple Blossom Festival

The 92nd Shenandoah Apple Blossom Festival

The 92nd Shenandoah Apple Blossom Festival

Apple Blossom’s Got Talent: FINALS

The 92nd Shenandoah Apple Blossom Festival

The 92nd Shenandoah Apple Blossom Festival

The 92nd Shenandoah Apple Blossom Festival

Opening Weekend at Kernstown Battlefield

The 92nd Shenandoah Apple Blossom Festival

Opening Weekend at Kernstown Battlefield

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Dog Agility Trials

Dog Agility Trials

Spring Open House and Range Day

The New Doc’s Meet

The Odd Couple

History and Civil War Walking Tour

Dog Agility Trials

Spring Open House and Range Day

The New Doc’s Meet

The Odd Couple

Apple Blossom Antique Car Show

Dog Agility Trials

The New Doc’s Meet

The Odd Couple

Garden Fair – Mother’s Day Weekend

The Odd Couple

The Odd Couple

The Odd Couple

North-South Skirmish Association’s National Competition

The Odd Couple

North-South Skirmish Association’s National Competition

The Odd Couple

North-South Skirmish Association’s National Competition

Comedy Weekend

Lucketts Spring Market

The Odd Couple

North-South Skirmish Association’s National Competition

Comedy Weekend

Lucketts Spring Market

Old Town Farmers Market

The Odd Couple

North-South Skirmish Association’s National Competition

Lucketts Spring Market

The Odd Couple

The Odd Couple

The Odd Couple

The Odd Couple

Sunset Series on the Garden Rooftop

The Odd Couple

Newtown Heritage Festival

The Odd Couple

Newtown Heritage Festival

Old Town Farmers Market

aMuse Art & Craft Festival

Twilight Hike

aMuse Art & Craft Festival

Loudoun Street Mile

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Winchester Craft Beer Week

Garden Fest

Old Town Farmers Market

Winchester Wings & Wheels

Tiffany Exhibition Opening

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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 a 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

The 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.