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 September 2019

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Calendar of Events

Calendar of Events
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Labor Day Movie Marathon at Drive-In

Mexican Fiesta Lunch

Preview Screening: Patsy Cline & Country Music, A Film by Ken Burns

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Steel Magnolias

Friday Fish Fry Celebration

Steel Magnolias

Old Town Farmers Market

Cat Fanciers of Washington: Cat Show

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FallFest at Belle Grove Plantation

Winchester Wedding Expo

Farm to Table Dinner

Steel Magnolias

Steel Magnolias

Steel Magnolias

Steel Magnolias

Skyline Indie Film Fest

Steel Magnolias

Skyline Indie Film Fest

Shenandoah University’s Inaugural Esports Summit

Progressive Dinner – Farm to Table

History and Civil War Walking Tour

Steel Magnolias

Skyline Indie Film Fest

Shenandoah University’s Inaugural Esports Summit

Farm to Fork Fondo

Old Town Farmers Market

Steel Magnolias

Skyline Indie Film Fest

Farm to Fork Fondo

Kitchen Kapers

275th Anniversary of Winchester Talk by Dr. Carl Ekberg

Steel Magnolias

Steel Magnolias

Steel Magnolias

Steel Magnolias

Watermelon Park Fest

Steel Magnolias

Watermelon Park Fest

Winchester Arts & Music Festival

Skyline Area 51: Project Laser Tag

Shenandoah Valley Apple Harvest Festival

Steel Magnolias

Watermelon Park Fest

Winchester Arts & Music Festival

Smithsonian Magazine Museum Day – FREE admission

Shenandoah Valley Apple Harvest Festival

Watermelon Park Fest

Winchester Arts & Music Festival

French and Indian War Weekend

Celebracion of Winchester Festival

Winchester Restaurant Week

Winchester Arts & Music Festival

Skyline Laser Tag Glow Night

Winchester Restaurant Week

Winchester Restaurant Week

Winchester Restaurant Week

Tri-State Antique Truck Show

Winchester Restaurant Week

Tri-State Antique Truck Show

Winchester Restaurant Week

Tri-State Antique Truck Show

Old Town Farmers Market

Solenberger’s True Value Hardware Car/Truck/Motorcycle Show

2019 European Festival

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French Wine Class

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North-South Skirmish Association: Fall National Competition

History at Sunset

North-South Skirmish Association: Fall National Competition

6th Annual Parks and Pets Extravaganza

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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.