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 February 2019

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Calendar of Events

Calendar of Events
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Backroom Blowout Wine Tasting

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Groundhog Day Celebration

Unheard Voices of Civil War Winchester

Black History Month Talk: Abe Spencer

Historic Winchester Food Tours

Winchester Beer Tour

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Aphrodisiac Cooking & Wine Pairing

Handley Library Behind-the-Scenes Tour

Civil War Roundtable

Stagedoor New Scripts Festival

Chocolate Escape

Stagedoor New Scripts Festival

Historic Winchester Food Tours

Murder Mystery Comedy Show

Stagedoor New Scripts Festival

Winchester Beer Tour

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Haunted Hearts: An Evening With Psychic Mediums & Card Readers

Two Pints by Abbey Theatre

Apple Blossom’s Got Talent First Audition

Two Pints by Abbey Theatre

Valentine’s Day Couples Craft Night

Two Pints by Abbey Theatre

Comedy Weekend

You’re a Good Man, Charlie Brown!

Two Pints by Abbey Theatre

Comedy Weekend

You’re a Good Man, Charlie Brown!

MSV Day: Free Admission

Valentine’s Wine and Cupcake Pairing

Two Pints by Abbey Theatre

You’re a Good Man, Charlie Brown!

Winchester Beer Tour

Valentine’s Dessert Tour

Restaurant Week

President’s Day Event at Fort Loudoun

George Washington’s Office Museum Open House

Restaurant Week

Restaurant Week

Restaurant Week

Restaurant Week

George Washington’s Birthday Cocktail Party

Restaurant Week

Exploring Your Civil War Roots

Historic Winchester Food Tours

Winchester Beer Tour

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Historic Winchester Food Tours

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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.