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 April 2019

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Calendar of Events

Calendar of Events
Sunday Monday Tuesday Wednesday Thursday Friday Saturday

Winchester Beer Tour

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April Morning Garden Walk

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Shenandoah University McCormick Civil War Institute’s Annual Spring Conference

Cars for a Cause Nostalgic Car Show

Kite Flying Festival

Silkroad Ensemble Concert

Comedy by The Capitol Steps

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Apple Blossom’s Got Talent Semi-Finals

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Patsy Cline Classic: Sara Evans in Concert

Abram’s Creek Nature Walk

Scottish “Backyard” Highland Games

Annual Wits for Wellness 5k Run/Walk

John Kirby Jazz Day

Crawl for a Cure Charity Pub Crawl

Rally in the Alley

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Sunset Series on the Garden Rooftop

Orchid Show and Sale

Comedy Weekend

Orchid Show and Sale

Comedy Weekend

Old Town Easter Egg Hunt

Easter Eggstravaganza

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Apple Blossom Festival: Bloomin’ Wine Fest

The 92nd Shenandoah Apple Blossom Festival

Così fan tutte

Apple Blossom Festival: Bloomin’ Wine Fest

The 92nd Shenandoah Apple Blossom Festival

Così fan tutte

Abram’s Creek Nature Walk

Virginia’s Historic Garden Week Tour

The 92nd Shenandoah Apple Blossom Festival

Così fan tutte

Apple Blossom Festival: Winchester Ciderworks Tasting and Orchard Tours

The 92nd Shenandoah Apple Blossom Festival

The 92nd Shenandoah Apple Blossom Festival

The 92nd Shenandoah Apple Blossom Festival

The 92nd Shenandoah Apple Blossom Festival

The 92nd Shenandoah Apple Blossom Festival

The 92nd Shenandoah Apple Blossom Festival

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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.