Event Type: Wineries, Breweries & Distilleries

Shenandoah Apple Blossom Festival featured event – United Bank Bloomin’ Wine Festival
Located in downtown Winchester
Winchester, VA 22602

Shenandoah Apple Blossom Festival featured event – United Bank Bloomin’ Wine Fest
Located in downtown Winchester
Winchester, VA 22602

2fer 2sday is a high-energy 90s cover band that brings the best of grunge and alternative rock to the stage, delivering a nostalgic punch of back-to-back hits. Since their formation in 2022, they’ve mastered the anthems of the decade, covering iconic bands like Bush, Radiohead, and Foo Fighters. Whether it’s a weekend party or a weekday escape, 2fer 2sday guarantees a trip back to the golden age of 90s rock—because with them, every night feels like Tuesday!

Shenandoah Apple Blossom Festival featured event – Fiesta Latina

Check website for full details.

Sportsplex
221 Commonwealth Court
Winchester

Join us for an afternoon of live music with Adam Phelps, whose smooth vocals and acoustic guitar bring a heartfelt blend of classic country and bluegrass to life. Growing up on a farm in western Frederick County, Virginia, Adam’s music is deeply rooted in his family’s musical influence and his love for sharing authentic stories. His rich life experiences as a father, grandfather, and husband of 25 years shine through every note. Sip on your favorite Wolf Gap wine and savor the magic of Adam’s soulful performance in our beautiful vineyard setting

Celebrate the start of May!

The Punky Brewsers are a dynamic trio, featuring Joe Martin on drums, Paul Jannicola on guitar/vocals, and Philip Taylor on bass/vocals, will have you singing and dancing to punk and rock hits from across the decades.

Shenandoah Apple Blossom Festival featured event – Claudio’s Pizzeria 80’s Dance Party

Check website for details

Tolley Dental Zone at James R. Wilkins Athletics & Center
1188 Ralph Shockey Drive
Winchester, VA

Shenandoah Apple Blossom Festival featured event – American Woodmark Fireworks Show

John Handley High School
425 Handley Blvd
Winchester, VA

Lower end of campus, Valley Ave

Check website for details

Shenandoah Apple Blossom Festival featured event – Valley Health 10K Race

John Handley High School
425 Handley Blvd.
Winchester, VA

Shenandoah Apple Blossom Festival featured event – Partlow Insurance Sports Breakfast

Tolley Dental Zone at James R. Wilkins Athletics & Center SU
1188 Ralph Shockey Drive
Winchester, VA

Check website for details

Shenandoah Apple Blossom Festival featured event – GloFiber Grand Feature Parade

Starts Downtown at Cork & Cameron Street and ends on Handley Blvd., Winchester, VA

Check website for details

Shenandoah Apple Blossom Festival featured event – Kids’ Bloomin’ Race presented by Rubbermaid Commercial Products
Check website for details.
John Handley High School
425 Handley Blvd.
Winchester, VA 22601

Shenandoah Apple Blossom Festival featured event – Malloy Totoya Country Music Party

Tolley Dental Zone at James R. Wlkins. Jr. Athletics & Events Center SU
1188 Ralph Shockey Drive
Winchester

Check website for details

Shenandoah Apple Blossom Festival featured event – Contemporary Christian Concert presented by Clean Water of Virginia

Tolley Dental Zone at James R. Wlkins. Jr. Athletics & Events Center SU
1188 Ralph Shockey Drive
Winchester

Check website for details

Relax away your Saturday with us and the exceptionally talented Ryan Thomas. Originating from the lively locale of Stephens City, Virginia, Ryan brings his musical prowess to our stage, promising an unforgettable performance you won’t want to miss

Come out and enjoy live music with the talented Hannah Jeanne! Enjoy breathtaking views, food, and our amazing wines.

Join us at Wolf Gap Vineyard for an unforgettable live music event featuring Brennan Edwards, an independent artist from Frederick County, Virginia.

Brennan’s captivating performances showcase his talent and passion through heartfelt covers of artists like Hank Williams, John Prine, Tyler Childers, and Blue Moon Rising.

Shenandoah Apple Blossom Festival featured event – Winchester Police Department Car Show

Saturday, May 24   | Noon – 4:00pm
​Rain Date May 25

Piccadilly St. from Cameron St. to Washington St.
Loudoun St. from Piccadilly St. to Fairfax St.
Old Town Winchester

Check website for details

What’s better than a weekend trip to Wolf Gap Vineyard?

Come out enjoy a glass of your favorite Wolf Gap wine while enjoying live music with Pappy and Sam Dinges. It is sure to be a great time, and we hope to see you there

Join us for an afternoon of live music with Adam Phelps, whose smooth vocals and acoustic guitar bring a heartfelt blend of classic country and bluegrass to life. Growing up on a farm in western Frederick County, Virginia, Adam’s music is deeply rooted in his family’s musical influence and his love for sharing authentic stories. His rich life experiences as a father, grandfather, and husband of 25 years shine through every note. Sip on your favorite Wolf Gap wine and savor the magic of Adam’s soulful performance in our beautiful vineyard setting

Relax away your Saturday with us and the exceptionally talented Ryan Thomas. Originating from the lively locale of Stephens City, Virginia, Ryan brings his musical prowess to our stage, promising an unforgettable performance you won’t want to miss

Experience the soulful sounds of Tucker Wyatt, a rising star in the indie country and outlaw Americana scenes. Tucker’s music is a heartfelt blend of raw storytelling and evocative melodies, inspired by the Chesapeake Bay and the rich traditions of the American South. With his band, the Mothertuckers, he delivers a high-energy performance that takes you on a journey through love, grit, and self-discovery. Grab a glass of wine and join us for a night of incredible music!

Step back in time with the incredible Robbie Limon, a masterful entertainer who brings the iconic sounds of the ’70s to life with his uncanny ability to replicate the voices of the era’s greatest singers. Whether you’re a fan of classic hits or just love a night of expertly crafted live music, Robbie’s performance is sure to rekindle memories and create new ones. With over 200 shows a year, he’s graced stages big and small, always leaving audiences raving.