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 November 2019

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Calendar of Events

Calendar of Events
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Ravenwood Faire

28

Halloween (1978) at the Alamo Drafthouse Cinema

Halloween (1978) at the Alamo Drafthouse Cinema

Haunted History Ghost Tour

Harvest Party and Trunk-or-Treat

History and Hauntings

Halloween (1978) at the Alamo Drafthouse Cinema

Haunted History Ghost Tour

Matthew Modine Weekend

First Friday in Old Town

Monster Bash

Battlefield Half Marathon

Matthew Modine Weekend

Antiques Appraisal Fair

Comedy Hypnotist: Gary Conrad

Oyster and Wine Event

Matthew Modine Weekend

Antiques Appraisal Fair

Wine Tasting

Winchester Beer & Cider Tour

Magic Lantern at MSV: Free Solo

Ginkgo Grove Tours

5
6
7

Winchester Little Theatre: Theft

History and Hauntings

The Bridge-Led Zeppelin Tribute Live at Bright Box

African American History Day

Winchester Little Theatre: Theft

Bakery Festival

Crossroads of History Conference

Top of Virginia Bluegrass Series

Winchester Little Theatre: Theft

Winchester Beer & Cider Tour

History at Sunset

11
12

Trivia Night: The Office Episode 1

Winchester Little Theatre: Theft

Macbeth

Winchester-Frederick County History Trivia Night

Winchester Little Theatre: Theft

Macbeth

Comedy Weekend

Winchester Little Theatre: Theft

Macbeth

Comedy Weekend

Virginia Gourd Show and Sale

Scottish “Backyard” Highland Games

Winchester Little Theatre: Theft

Macbeth

Virginia Gourd Show and Sale

Winchester Beer & Cider Tour

18
19
20

Winchester Little Theatre: Theft

Beaujolais Nouveau And Cru Beaujolais

Robbie Limon & Friends Live at Bright Box

Winchester Little Theatre: Theft

Bough and Dough Shop

Flower Show

Deck the Walls Holiday Market

History and Hauntings

Winchester Little Theatre: Theft

Bough and Dough Shop

Flower Show

Deck the Walls Holiday Market

Frozen Celebration

Winchester Beer & Cider Tour

25

Deck the Walls Holiday Market

Bough and Dough Shop

Thanksgiving Centerpiece Workshop

Deck the Walls Holiday Market

Bough and Dough Shop

28

Plaid Friday and Shop Small Saturday

Deck the Walls Holiday Market

Bough and Dough Shop

Plaid Friday Walking Tour

Walking in a Winter Wonderland

Plaid Friday and Shop Small Saturday

Walking in a Winter Wonderland

Shenandoah Potters Guild Holiday Show

The Nutcracker

West Oaks Farm Market Holiday Craft Bazaar

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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.