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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Winchester Little Theatre presents: Baskerville

September 10 - September 25
Winchester Little Theatre, 315 W. Boscawen St.
Winchester, VA 22601 US

Get your deerstalker cap on — the play’s afoot! Sherlock Holmes and Dr. Watson must crack the mystery of “The Hound of the Baskervilles” before a family curse dooms its newest heir. Can our heroes discover the truth in time? Join the fun and see how far from elementary the truth can be. Written by ... Read more

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September 24 @ 5:00 PM - 10:00 PM
Old Town Winchester, 1 North Loudoun Street
Winchester, VA 22601 United States

Old Town Winchester Business Association and Literacy Volunteers are excited to present Old Town Winchester Oktoberfest 2021! This Beer Festival will feature local and breweries from around Virginia. Admission will include 10 tastings and a commemorative tasting glass. Advanced Tickets are $25, day of tickets will be $30. Be sure to Pre-order your T-shirt to ... Read more

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French and Indian War Weekend

September 25 - September 26
Abram’s Delight Museum, 1340 S. Pleasant Valley Rd.
Winchester, VA 22601 US

Join us for a weekend of living history at the French and Indian War Weekend! 18th Century Colonial Encampments Drilling and Musket Presentations Two Battle/Skirmishes Historical Interpretation of Colonial Forces in the French and Indian War Tours of Abram's Delight, Winchester's oldest home Free admission

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Sunflower Festival

September 25 @ 10:00 AM - 5:00 PM
The Homestead Farm at Fruit Hill Orchard, 2502 N. Frederick Pike
Winchester, Virginia 22603 US

It's The Homestead Farm's 1st Sunflower Festival! Sunflower fields, live music, games for kids, face painting, bounce house, food truck, hand-dipped ice cream and more! More details coming very soon! Tickets:

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Guided Civil War Walking Tour of Stephens City

September 25 @ 10:30 AM - 11:30 AM
Newtown History Center, 5408 Main St.
Stephens City, VA 22655 US

Civil War walking tours of historic Stephens City are conducted at 10:30 a.m. on the 4th Saturday of the month, beginning in June and ending in October. Tours are led by staff of the Newtown History Center. This tour focuses on the impact of the Civil War on the town. Learn about various civilian and ... Read more

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Dedication of Maine Monument at Third Winchester Battlefield

September 25 @ 1:00 PM
Third Winchester Battlefield, 541 Redbud Road
Winchester, VA 22603

Third Winchester Battlefield Park Winchester (Saturday, September 25, 2021, 1pm) The dedication of a new Union monument in honor of the 2,000 soldiers from Maine who fought at the Third Battle of Winchester on September 19, 1864. The program is free, but pre-registration is required. To register:

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Tour of Second Winchester Battlefield (McCann Property)

September 25 @ 2:30 PM - 3:30 PM
Third Winchester Battlefield, 541 Redbud Road
Winchester, VA 22603

Guided Tour of the McCann Property at Second Winchester led by historian Scott Mingus (Saturday, September 25, 2021, 2:30pm) The first-ever opportunity to tour the McCann Property, which was at the heart of the climactic action during the Second Battle of Winchester (fought on June 13-15, 1863). The tour will be led by Scott Mingus, ... Read more

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Shenandoah Valley Battlefields Foundation 25th Anniversary Celebration

September 25 @ 6:30 PM
Shenandoah University – James R. Wilkins, Jr. Athletic and Events Center, 1188 Ralph Shockey Drive
Winchester, VA 22601 United States

Join as we look back on 25 years of accomplishment with a star-studded red carpet event that will feature fine food, elegant music, and special guests and dignitaries, including former Congressman Frank Wolf and our keynote speaker, legendary Civil War historian Dr. James M. McPherson. The evening's events will include: • A red carpet entrance ... Read more

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Quentin Walton Trio in Concert

September 25 @ 7:00 PM - 10:00 PM
The Flat 9 Jazz Club, 100 N. Loudoun Street
Winchester, Virginia 22601

The Quentin Walston Trio is thrilled to hit the Flat Nine stage! Heralded as "stunning" and "impeccable" by Clarke Monthly, the Quentin Walston trio blends memorable melodies and striking rhythms with adventurous improvisations. Quentin Walston (piano) along with Daniel Kelly II (drums) and Ben Rikhoff (bass) will be performing exciting originals including the group’s new ... Read more

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Reader’s Theatre: Red Hot Mamas

September 26 @ 6:30 PM
Winchester Little Theatre, 315 W. Boscawen St.
Winchester, VA 22601 US

Abby and Dan are newly minted empty nesters. Their peace and solitude is interrupted when their odd couple widowed mothers-in-law move in, and chaos and hilarity ensues. A fun romp proving that sexy and funny are timeless and ageless. Written by David Christner Directed by Debbie Miles & Leandra Ganci Stotler Tickets $5, FREE FOR ... Read more

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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

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.