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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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6 events,
Our World in Stitches: 2024 Elaine Evans Embroidery Show
The Winchester Chapter of the Embroiderers’ Guild of America is excited to announce its 2024 Elaine Evans Embroidery Show OUR WORLD IN STITCHES. The exhibition will be held from April 20th to May 11th at Godfrey Miller Center. Address: 28 S Loudoun St., Winchester, VA 22601. This year we invite everyone to join us for ... Read more
Apple Blossom Festival: Pickleball Tournament
The tournament will be hosted by the Winchester Country Club and is one of many events held as part of the 97th Shenandoah Apple Blossom Festival® from April 26 - May 5. This is a non-sanctioned indoor tournament being held at the Winchester Country Club with split Age and Skill Divisions in Men's and Women's ... Read more
Apple Blossom Festival: Carnival
The Apple Blossom Carnival Powers Great American Midway is your ticket to fun and excitement for all ages. From thrill seeking rides to midway games, the Apple Blossom Carnival offers a variety of activities for the entire family. The “Pay One Price” is offered and can be purchased at the carnival site. Powers Great American ... Read more
Apple Blossom Festival: Tennis Tournament
The Shenandoah Apple Blossom Festival® is excited to announce the return of its annual USTA-sanctioned tennis tournament. Now in its 8th year, the event promises to be competitive and exciting for tennis players of all levels. The success of the tournament grows each year, attracting local and out-of-town tennis players and spectators. Registered participants receive ... Read more
Live Opera: Moscow, Cheryomushki
Friday, April 26 at 7:30PM Saturday, April 27 at 7:30PM Sunday, April 28 at 2:30PM Main Stage Opera with Symphony Orchestra Music by Dmitri Shostakovich Arranged by Gerard McBurney Libretto by Vladimir Mass and Mikhail Chervinsky Main Stage Opera provides audiences with the full opera experience! This year’s production follows a group of friends in ... Read more
Apple Blossom Festival: Fiesta Latina
Apple Blossom Festival: Fiesta Latina
The 97th Shenandoah Apple Blossom Festival® 2nd Annual Fiesta Latina Event is focused on our Hispanic/Latino Community in Winchester and surrounding areas. Hispanic Traditions will be on display as we celebrate the Culture with its best local cuisine, arts, and entertainment! Together, we can celebrate the Apple Blossom Festival's Fiesta Latina! Spanish translation: El segundo ... Read more
4 events,
Apple Blossom Festival: Pumps & Pearls Ladies Party
Apple Blossom Festival: Pumps & Pearls Ladies Party
Pumps and Pearls, the ultimate ladies’ night out, will return to the George Washington Hotel! We were there last in 2019! Dancing, appetizers, drinks, photo booth, prizes, and of course our famous shoe contest are the highlight of the evening! Participation in the shoe contest is optional, but categories include the following: Personal Pump Creations; ... Read more
4 events,
Apple Blossom Festival: 100th Birthday Celebration
Apple Blossom Festival: 100th Birthday Celebration
It's time to mark a century of memories, joy, and community spirit as the Shenandoah Apple Blossom Festival® celebrates its 100th birthday in style. Join us for an unforgettable evening filled with family fun at the 100th Birthday Party, hosted by the Festival. This milestone celebration promises an array of entertainment for all ages, including ... Read more
Trailblazing Women of Country
Trailblazing Women of Country
Performing Arts Live Trailblazing Women of Country: From Patsy to Loretta to Dolly Featuring Miko Marks & Kristina Train Patsy Cline, Loretta Lynn and Dolly Parton revolutionized country music and blazed a trail for future generations of female artists. With their chart-topping hits, record-breaking sales and designations in the Country Music Hall of Fame, their ... Read more
3 events,
Apple Blossom Festival: Business at the Bloom
Apple Blossom Festival: Business at the Bloom
Valley Health Business at the Bloom is one of the largest gatherings of regional business leaders during the entire year. Offering a terrific speaker and the opportunity to network with others in the business community, the luncheon is the perfect opportunity to entertain clients or reward valued employees. Business at the Bloom is a great ... Read more
5 events,
Apple Blossom Festival: Kids’ Bloomin’ Mile
Apple Blossom Festival: Kids’ Bloomin’ Mile
Experience the thrill of running in one of the premier kids races in the area. Enjoy the sights and sounds of running around John Handley High School during one of the opening events for the Shenandoah Apple Blossom Festival. Sign Up: https://runsignup.com/Race/VA/Winchester/AppleBlossomValleyHealth10K
Apple Blossom Festival: Firefighters’ Parade
Apple Blossom Festival: Firefighters’ Parade
Coordinated by members of the Winchester and Frederick County firefighters for the 89th year, the Firefighters’ Parade will step off at 5:30 p.m. Friday, May 3rd Come downtown to the Midway for carnival food, games and entertainment and then head over to the parade route to see the Antique Firetruck's start with the pre-parade, some ... Read more
Apple Blossom Festival: Fireworks Show and Music Fest
Apple Blossom Festival: Fireworks Show and Music Fest
Join us for an incredible fireworks display on the grounds of Handley High School! The American Woodmark fireworks display offers something for everyone. Walk from the Old Town Midway and along the firefighter’s parade route to Handley High School campus, find a perfect spot on the lawn and watch the American Woodmark fireworks show! People ... Read more
4 events,
Apple Blossom Festival: Valley Health 10K
Apple Blossom Festival: Valley Health 10K
Enjoy the sights, sounds and the experience of the Shenandoah Apple Blossom Festival, while running through the streets of downtown Winchester. The Valley Health 10k has been a fan favorite event for over 38 years! Sign Up: https://runsignup.com/Race/VA/Winchester/AppleBlossomValleyHealth10K
Apple Blossom Festival: Grand Feature Parade
Apple Blossom Festival: Grand Feature Parade
Since 1941 the Winchester Host Lions Club has coordinated the glofiber Grand Feature Parade through the historic streets in downtown Winchester. The Grand Feature Parade will step off at 1:30 p.m. on Saturday afternoon and will include five parade divisions. From start to finish the parade is nearly 4 hours long! The parade has special ... Read more
3 events,
Live Theatre: The Spitfire Grill
Winchester Little Theatre presents The Spitfire Grill. A heartwarming and inspirational musical tale of redemption, perseverance and family. Set in a small Wisconsin town and full of soulful, engaging music, it depicts the journey of a young woman looking for a second chance, and the multidimensional townspeople who end up embarking on a journey of ... Read more
Youth Trout Derby
Youth Trout Derby
The Youth Trout Derby is back! Visit Clearbrook Park on May 10th from 5-8pm for this exciting and engaging fishing event designed for young anglers (ages 4-14). This derby allows youth to connect with nature, learn or enhance fishing skills, and foster a love for the outdoors. With prizes, giveaways, and a focus on conservation, ... Read more
4 events,
ShenCoLab: Festival of Arts, Ideas & Exploration
Shenandoah Conservatory turns over the programming and facilities to its students for a week of unbridled exploration, collaboration and creativity. Students work across disciplines on self-directed, time-limited projects fueled by their own passion, drive and curiosity. The week culminates with a day-long Festival of Arts, Ideas & Exploration featuring a wide variety of exciting, innovative ... Read more
Of Ale and History Beer Festival
Of Ale and History Beer Festival
There will be more than 30 beers and ciders on tap to taste. This will be the first “Of Ale and History” Beer Fest for craft breweries and cideries Bear Chase Brewing Company (Bluemont), Denizens Brewing (Riverdale Park, MD), Jackie O’s Pub and Brewery (Athens, OH), Nepenthe Brewing Company (Baltimore, MD), Old 690 Brewing Company ... Read more
In The Round: A Jazz Poetry Experience
In The Round: A Jazz Poetry Experience
Jazz and Poetry come together in an improvisational spoken word and musical performance. For 90 minutes, musicians will perform a mixture of jazz and R&B while local poets bring prepared and improvised slam poetry as an instrument and an interlude. Poets include: Joseph M. Jablonkski (Walking Mall Poet and With Ink: Typewriter poets), Wayne ... Read more
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Arts Chorale of Winchester "Sojourn Salzburg" Concert
Arts Chorale of Winchester "Sojourn Salzburg" Concert
Arts Chorale of Winchester will perform some of the music from their trip to Salzburg, Austria this June. It will feature Mozart's Coronation Mass in C Major k. 317 with full orchestra and soloists. Other works include John Rutter's "For the Beauty of the Earth"; Brahms Requiem, "How Lovely is Thy dwelling-place"; Mack Wilberg's "Come, Thou Fount ... Read more
3 events,
Fort Loudoun Day Living History Event
Fort Loudoun Day Living History Event
Visit the site of Colonel George Washington's headquarters for the Virginia Regiment during the French & Indian War, 1756-1763. Learn about life on the Virginia frontier in the late 18th century and the French & Indian War era and how events during this period led to the founding of our country. Meet Living History Interpreters ... Read more
Arts Chorale of Winchester “Sojourn Salzburg” Concert
Arts Chorale of Winchester “Sojourn Salzburg” Concert
Arts Chorale of Winchester will perform some of the music from their trip to Salzburg, Austria this June. It will feature Mozart's Coronation Mass in C Major k. 317 with full orchestra and soloists. Other works include John Rutter's "For the Beauty of the Earth"; Brahms Requiem, "How Lovely is Thy dwelling-place"; Mack Wilberg's "Come, Thou Fount ... Read more
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Healing Field of Honor
United States flags will fly again in a solemn formation during May of 2024 creating an awe-inspiring panorama. This stirring display of several hundred flags will bring our community together in a patriotic tribute to honor our heroes. Each U.S. flag represents an individual and tells a story. Flags may be sponsored to honor individuals ... Read more
3 events,
🥂🎤 Karaoke & Wine Night! Vines & Vocals
🥂🎤 Karaoke & Wine Night! Vines & Vocals
BOOK YOUR RESERVATION AT THE LINK, OR BY CALLING US AT (540) 931-5452* 🎤🍷 𝐆𝐞𝐭 𝐫𝐞𝐚𝐝𝐲 𝐭𝐨 𝐮𝐧𝐥𝐞𝐚𝐬𝐡 𝐲𝐨𝐮𝐫 𝐢𝐧𝐧𝐞𝐫 𝐬𝐮𝐩𝐞𝐫𝐬𝐭𝐚𝐫 𝐚𝐭 𝐨𝐮𝐫 𝐅𝐈𝐑𝐒𝐓 𝐄𝐕𝐄𝐑 𝐊𝐚𝐫𝐚𝐨𝐤𝐞 & 𝐖𝐢𝐧𝐞 𝐍𝐢𝐠𝐡𝐭 𝐨𝐧 𝐌𝐚𝐲 𝟐𝟒𝐭𝐡, 𝐟𝐫𝐨𝐦 𝟕 - 𝟗 𝐏𝐌! Join us at James Charles Winery for an unforgettable evening of melodious fun, hosted by the local sensation 𝐃𝐚𝐧 𝐭𝐡𝐞 𝐊𝐚𝐫𝐚𝐨𝐤𝐞 𝐌𝐚𝐧 𝐟𝐫𝐨𝐦 𝐃𝐚𝐧 𝐌𝐜𝐃𝐞𝐫𝐦𝐨𝐭𝐭'𝐬 𝐊𝐚𝐫𝐚𝐨𝐤𝐞 𝐒𝐡𝐨𝐰.𝘼𝙙𝙢𝙞𝙨𝙨𝙞𝙤𝙣 𝙞𝙨 𝙖𝙗𝙨𝙤𝙡𝙪𝙩𝙚𝙡𝙮 𝙁𝙍𝙀𝙀! However, seats are expected to fill up fast, so we recommend making your reservations early. 𝐃𝐨𝐧'𝐭 𝐦𝐢𝐬𝐬 𝐨𝐮𝐭 on your chance to shine in the spotlight or ... Read more
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Winchester Police Department Car Show
Winchester Police Department Car Show
The Winchester Police Department Car Show began in 2022 to celebrate the department’s 200 year anniversary. The event was designed to bring the community to downtown Winchester to enjoy a day with classic cars and in historic downtown Winchester. All of the event’s proceeds are donated to the Frederick County/Winchester Law Enforcement Foundation. Show hours ... Read more
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Loudoun Street Mile
Loudoun Street Mile
The Loudoun Street Mile is an anticipated event for regional runners, held annually on Memorial Day in Old Town Historic Winchester. Celebrating its 37th year, this race attracts participants eager to traverse the iconic Loudoun Street, combining the thrill of competition with the charm of the historic setting. This year’s race will serve as the ... Read more
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Musician’s Mastermind Challenge
Musician’s Mastermind Challenge
Want to learn how to take your musical and artistic talent to the next level? Get out your pen and paper and join renown drummer and music coach, Daniel Kelly II, as he shares his knowledge and expertise in teaching aspiring artists (musicians, singers, dancers, etc.) in how to enhance their craft to grow significant ... Read more
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Hop Blossom Craft Beer Festival
Hop Blossom Craft Beer Festival
Love beer? Want to help doggies and kitties? Join us for the annual Hop Blossom Craft Beer Festival held in Old Town Winchester, Virginia. The festival features amazing crafters, tasty treats, a bounty of brews and loads of fun! Even better? The event benefits Dakota’s Dream Animal Rescue, a small, volunteer run, no-kill, non-profit animal ... Read more
Triple Peak Gran Fondo
Triple Peak Gran Fondo
Element Adventures is proud to announce the 2024 Triple Peak Gran Fondo! The Triple Peak route has it all: plenty of miles, beautiful pastoral vistas, and stiff mountain climbs (with accompanying sweet descents!) The Double Peak and Single Peak routes provide shorter challenges, but adventure nonetheless! Over mostly rural roads, you’ll get to see the ... 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 a
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
The 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.
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