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.

Calendar of Events

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Newcomers Welcome Event

Shenandoah Conservatory Harp Ensemble with Claire Jones, former Royal Harpist

1 event,

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First Friday and Old Town Spirit

5 events,

Renegade Monster Truck Tour

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Author Event: Cleveland Eason – A Sailor’s Advice for Life

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Author Event: Chris Morehouse – Legacy: Wisdom of African Traditions and the Bible

A Century of Harmony: The George Washington Hotel Commences 100th Anniversary Concert Series with Orleans

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Story Time with Ashley Belote – Don’t Wash Winston

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FINAL 2024 BRUNCH BAR! Shrimp-n-Grits & Breakfast Casserole

William Chapman Nyaho

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Henry V

Henry V

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Studio Big Band

7 events,

Exhibition Opening: The Triumph of Nature: Art Nouveau from the Chrysler Museum of Art

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Author Event: Grant Harris – Unlocking the Power of Diversity, Equity & Inclusion for Success

Choral Ensembles

From Darkness To Light Presented By Winchester Music Viva

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Author Event: Ginny Fite – Leave Everything You Know Behind

From Darkness To Light Presented By Winchester Music Viva

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Contempo Ensemble

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Little Big Band

10 events,

Our World in Stitches: 2024 Elaine Evans Embroidery Show

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Solenberger’s Hardware Annual Car Show

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Sports Card, Pokemon, and Collectibles Show

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West Oaks Spring Vendor Fair

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McCormick Civil War Institute Spring 2024 Conference

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Apple Blossom Festival: Cider Tasting and Orchard Tours

4 events,

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Brunch & Bubbly

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Author Event: J.S. Clawson – The Hawk and the Hummingbird Series

BLUE RIDGE SINGERS SPRING 2024 CONCERT

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Apple Blossom Festival: Tennis Tournament

Apple Blossom Festival: Carnival

Apple Blossom Festival: Old Town Winchester Artisan and Crafter Show

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Apple Blossom Festival: Bloomin’ Wine Fest

Live Opera: Moscow, Cheryomushki

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Apple Blossom Festival: Breakfast with Miss Apple Blossom

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2024 Independent Bookstore Day

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Author Event: Magdalene Dietchka – The Physician & Riley Kilmore – Shay the Brave

6 events,

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Apple Blossom Festival: Fiesta Latina

4 events,

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Apple Blossom Festival: Pumps & Pearls Ladies Party

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Apple Blossom Festival: 100th Birthday Celebration

Trailblazing Women of Country

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Henry V

Henry V


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.