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.

PLEASE NOTE: Due to numerous cancellations of large gatherings due to COVID-19, these events are subject to change. Please call ahead to confirm that an event is still being held.

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Events for October 2020

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Calendar of Events

Calendar of Events
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Rocky Horror Picture Show at the Drive-In

Tomato Festival

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Hocus Pocus and Little Shop of Horrors at the Drive-In

Free First Friday

Chuggalug Live at West Oaks

Hocus Pocus and Little Shop of Horrors at the Drive-In

Trainwreck Live on the Boat

Hocus Pocus and Little Shop of Horrors at the Drive-In

Magic Lantern Theater presents: Fiddler: A Miracle of Miracles

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Toby Mac – Drive-In Theatre Tour

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Coco and Hocus Pocus at the Drive-In

Coco and Hocus Pocus at the Drive-In

Pumpkin Patch and Photos

Pick Your Own at Rinker’s Orchards

Burgers, Blues, and Brews Festival

Coco and Hocus Pocus at the Drive-In

Pick Your Own at Rinker’s Orchards

Winchester Tales Book Release

Pick Your Own at Rinker’s Orchards

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Tim Burton’s The Nightmare Before Christmas

Hocus Pocus and Nightmare Before Christmas at the Drive-In

Richard’s Apple Festival

Tim Burton’s The Nightmare Before Christmas

Hocus Pocus and Nightmare Before Christmas at the Drive-In

Fall Outdoor Craft Market

Battle of Cedar Creek Commemoration

Fall Outdoor Craft Market

Battle of Cedar Creek Commemoration

Bumpin’ Uglies Live at the Drive-In

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Hocus Pocus with Goosebumps at the Drive-In

Fore the Kids Golf Tournament

Chance McCoy of Old Crow Medicine Show w Mink’s Miracle Medicine

Pumpkin Festival

Hocus Pocus with Goosebumps at the Drive-In

Second Battle of Kernstown Tour

COVID-19 Memorial

Off the Rails Cabaret

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Hocus Pocus and Goosebumps at the Drive-In

Ravenwood Faire

Hocus Pocus and Goosebumps at the Drive-In

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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.