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 December 2019

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Calendar of Events

Calendar of Events
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Patsy Cline Holiday House Tours

Middletown Christmas Parade

Shenandoah Potters Guild Holiday Show

The Nutcracker

Walking in a Winter Wonderland

Christmas Parade and Tree Lighting Ceremony

Walking in a Winter Wonderland

Walking in a Winter Wonderland

Deck the Walls Holiday Market

Bough and Dough Shop

Walking in a Winter Wonderland

Deck the Walls Holiday Market

Bough and Dough Shop

Trivia Night: Harry Potter

Walking in a Winter Wonderland

Deck the Walls Holiday Market

Bough and Dough Shop

Patsy Cline Holiday House Tours

Walking in a Winter Wonderland

Holiday Tours

Candlelight Tours and Open House

Deck the Walls Holiday Market

Patsy Cline Holiday House Tours

Follow the Star – Living Nativity

Candlelight Tours and Open House

Holiday Tours

Walking in a Winter Wonderland

Follow the Star – Living Nativity

Merrimint in Middletown

Holiday House Tours

Patsy Cline Holiday House Tours

Walking in a Winter Wonderland

Holiday Tours

Walking in a Winter Wonderland

Holiday Tours

Walking in a Winter Wonderland

Deck the Walls Holiday Market

Bough and Dough Shop

Holiday Tea: Shenandoah Valley Traditions

Holiday Tours

Walking in a Winter Wonderland

Deck the Walls Holiday Market

Bough and Dough Shop

Holiday Tours

Walking in a Winter Wonderland

Deck the Walls Holiday Market

Bough and Dough Shop

Patsy Cline Holiday House Tours

Holiday Tours

Walking in a Winter Wonderland

I Remember Christmas – Dinner Theater

Deck the Walls Holiday Market

Patsy Cline Holiday House Tours

Holly Jolly Old Town Celebration

I Remember Christmas – Dinner Theater

Holiday Tours

Walking in a Winter Wonderland

Patsy Cline Holiday House Tours

I Remember Christmas – Dinner Theater

Walking in a Winter Wonderland

Bough and Dough Shop

Holiday Tours

Holiday Tours

Walking in a Winter Wonderland

Holiday Tours

Walking in a Winter Wonderland

Holiday Tours

Walking in a Winter Wonderland

Trivia Night: Parks and Rec

Holiday Tours

Walking in a Winter Wonderland

Holiday Tours

Walking in a Winter Wonderland

Holiday Tours

Walking in a Winter Wonderland

Walking in a Winter Wonderland

Holiday Tours

Holiday Tours

Walking in a Winter Wonderland

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Holiday Tours

Walking in a Winter Wonderland

Holiday Tours

Walking in a Winter Wonderland

Holiday Tours

Walking in a Winter Wonderland

Walking in a Winter Wonderland

Holiday Tours

Holiday Tours

First Night Winchester

First Night Winchester

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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.