Blossom Ultimate DJ Party sponsored by Carter Myers Automotive
Tolley Dental Zone
James R. Wilkins Athletics & Events Center
1188 Ralph Shockey Drive
Winchester, VA 22602
Check website for full details
Shenandoah Apple Blossom Artisan & Faire
Blossom Artisan & Faire
Frederick County Fairgrounds
250 Fairground Road
Clearbrook, VA 22624
Check website for full details
April 26th – 10 a.m. to 6:00 PM
April 27th – 11:00 AM to 4:00 PM EDT
Ryan Jewel at Wolf Gap Vineyard
Get ready for an incredible afternoon as Nashville artist Ryan Jewel takes the stage at Wolf Gap Vineyard for the very first time! A Virginia native from the Shenandoah Valley, Ryan brings his rich baritone vocals and authentic songwriting to life, blending classic country with a fresh, relatable sound. Having shared the stage with legends like Blake Shelton and Luke Bryan, Ryan’s heartfelt performances and “what you see is what you get” style promise a true country music experience. Don’t miss this special event at the vineyard—grab a glass of wine and enjoy the magic!
Taylor LaFever at Wolf Gap Vineyard
A Shenandoah County native with a raspy, folk-infused voice that’s impossible to forget, Taylor LaFever blends Indie-Country, Folk, and Americana into a sound that’s all his own.
Don’t miss this rising star as he shares stories, songs, and a taste of his upcoming EP. Grab a glass of wine, soak in the tunes, and join us for an unforgettable evening! 
Learn more at https://lafevermusic.com/home
Robbie Limon at Wolf Gap Vineyard
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.
Tucker Wyatt at Wolf Gap Vineyard
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!
Open Mic Night at Wolf Gap Vineyard
Got a song to sing, a joke to tell, or a story to share? Join us for Open Mic Night, where the stage is yours! Whether you’re a musician, comedian, poet, or just want to try something new, come showcase your talent in a warm and welcoming atmosphere.
Enjoy great wine, friendly faces, and a chance to shine under the spotlight! Perform solo or bring friends to cheer you on. Let’s make it a night to remember filled with creativity, laughter, and music!
First Come First Serve and we have the mic and speakers set up for you! Up to 15 minutes for each performance
Ryan Thomas at Wolf Gap Vineyard
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
Alex Kearns at Wolf Gap Vineyard
Come give Alex Kerns a huge welcome for his first time playing at Wolf Gap Vineyard! From Berryville VA, Alex has been playing for 23 years. He is the cofounder of The Low Water Bridge Band. Come check out his music and find your new favorite musician!
Adam Phelps at Wolf Gap Vineyard
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
Matt Palmieri Wolf Gap Vineyard
Join us for an afternoon of view, wine, and live music with Matt Palmieri, a talented singer/songwriter from the Shenandoah Valley. Known for his dynamic performances, Matt delivers an eclectic mix of covers from icons like Tyler Childers, Zach Bryan, Johnny Cash, and Waylon Jennings, along with rock, Americana, and folk influences. His setlist, peppered with heartfelt original songs, creates a one-of-a-kind musical journey. Performing as a solo acoustic act, Matt’s raw talent and soulful style promise to captivate every listener. Don’t miss this incredible blend of storytelling and sound!
Jerry Wimmer & JJ at Wolf Gap Vineyard
Get ready for an electrifying afternoon of high-energy acoustic music blended with side-splitting comedic improvisation! 
Jerry Wimmer and JJ are talented performers who will keep you on the edge of your seat with their spontaneous musical creations and hilarious banter. Hope to see you there!
Jerry Wimmer and JJ are talented performers who will keep you on the edge of your seat with their spontaneous musical creations and hilarious banter. Hope to see you there!
Trivia Night at Wisteria Farm and Vineyard
Grab your best teammates! It’s Trivia Time – Disney Edition!
Are you the biggest Disney fan in town? Do you know more about Disney movies than your kids? Come out for Disney-themed trivia to find out.
Competition starts at 3:30 pm. Get here early to sign up and get settled before the questions start!
Trivia Night at Wisteria Farm and Vineyard
Grab your best teammates! It’s Trivia Time – Friends Edition!
Come see if you and your pals know the most about FRIENDS!
Buff up on your knowledge of the Central Park gang and compete for awesome FRIENDS prizes!!!
Competition starts at 3:30 pm. Get here early to sign up and get settled before the questions start!
Bourbon, Brandy & Burgers at L’Auberge Provencale
Enjoy a tasting of our private label bourbons: L’Auberge Provençale’s Buffalo Trace, Blanton’s, Eagle Rare, and Mt. Airy Reserve Maker’s Mark, served with our Ultimate L’Auberge Burger and house-cut fries. Plus, savor the pièce de résistance— a tasting of Hennessy XO with chocolate truffles.
$85 per person plus tax and gratuity.
Reserve your spot here or call us at 540-837-1375.
American Folk in the Shenandoah Valley
Scraposaurs in the Shenandoah Valley
Taylor LaFever at Wolf Gap Vineyard
Join us on Memorial Day for an afternoon of live music with local favorite, Taylor LaFever!
A Shenandoah County native with a raspy, folk-infused voice that’s impossible to forget, Taylor LaFever blends Indie-Country, Folk, and Americana into a sound that’s all his own.
Don’t miss this rising star as he shares stories, songs, and a taste of his upcoming EP. Grab a glass of wine, soak in the tunes, and join us for an unforgettable evening!
Learn more at https://lafevermusic.com/home
Jimmy Lee at Wolf Gap Vineyard
Jimmy Lee is an experienced artist who masterfully covers three decades of music across multiple genres. Known for his dynamic performances, Jimmy specializes in engaging the crowd and creating a deep connection with his audience. Whether it’s a lively event or an intimate gathering, Jimmy’s talent and charisma ensure a truly enjoyable and unforgettable experience for everyone in attendance.
Hope to see you there!
Learn more about Jimmy here: https://www.facebook.com/jimmyleelivemusic/
Pappy and Sam Dinges at Wolf Gap Vineyard
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
Girl Meets Boy at Wolf Gap Vineyard
Girl Meets Boy is an eclectic musical duo that rocks out to multiple genres, delivering a captivating and energetic performance. With their unique blend of sounds and dynamic stage presence, they promise a good time for every listener, leaving you dancing and singing along to your favorite hits!
Learn more about them here: https://www.facebook.com/girlmeetsboymusic
Brennan Edwards at Wolf Gap Vineyard
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.
Open Mic Night at Wolf Gap Vineyard
Got a song to sing, a joke to tell, or a story to share? Join us for Open Mic Night, where the stage is yours! Whether you’re a musician, comedian, poet, or just want to try something new, come showcase your talent in a warm and welcoming atmosphere.
Enjoy great wine, friendly faces, and a chance to shine under the spotlight! Perform solo or bring friends to cheer you on. Let’s make it a night to remember filled with creativity, laughter, and music!
First Come First Serve and we have the mic and speakers set up for you! Up to 15 minutes for each performance
Hannah Jeanne at Wolf Gap Vineyard
Come out and enjoy live music with the talented Hannah Jeanne! Enjoy breathtaking views, food, and our amazing wines.