Jesse Bauman, a renowned guitarist and music artist, offers his versatile talents for collaborations and projects in the vibrant music scene of southwest Wisconsin.

Andy Braun is a singer/songwriter with a folk-rock feel. He plays a wide variety of cover songs as he graces our stage!

Join us on National Wine & Cheese Day July 25th!

If you've seen Keith & The Klassics before you know! If you haven't you'll want to find your way here for a really fun afternoon of great music!

JTB plays acoustic covers of rock, pop, 90's, and country hits - -Solo, duo, trio, 4-piece arrangements, artists include Tom Petty, George Michael, Bill Withers, CCR, Rolling Stones, Beatles

Drew rocks the stage on Friday night!

Derek regularly performs throughout the midwest with his band Diamonds & Lead and as an acoustic solo

Americana, Rock and more Taylor does it all!

Wisconsin-based musical duo featuring instrumentalist/vocalist Britton Rea & vocalist Sarah Krahn.

Gin Mill Hollow is a high-energy Americana-jamband from Madison, WI, known for their unique blend of bluegrass, folk, jazz, blues, and rock. The quartet has developed a strong following through more than 600 live shows across the Midwest and beyond.

This is American music, back to basics with a three piece band playing early Rock-'n-Roll,

It's National Red Wine Day! Come enjoy a glass from our excellent selection!

Chasing denver is back with a splash from Fort Myers, FL! They will be playing from 3-6PM with Brian Matteson opening for them from 11-2PM! We highly encourage everyone to bring their own lawn chairs. No coolers are permitted and all  backpacks will be checked as carry ins are not allowed.

https://baileysrunvineyard.ticketspice.com/chasing-denver-september-2026

Come celebrate the long Labor Day weekend with us!

Join us for our 7th Annual Grape Stomp at Bailey's Run Vineyard & Winery on September 12, 2026!

Everyone who plans to stomp must pre-purchase tickets online. A team = 2 people; one who stomps the grapes and the other gathers juice. The team who produces a specific amount of juice the fastest will be the winner. The registration fee includes stomping competition, commemorative T-shirt per team member and 1 drink ticket good for a glass of wine or beer. Fastest teams then compete in the FINAL CRUSH. Winners of the FINAL CRUSH will receive a bottle of wine per team member.

Following all competitive stomping heats we will have:

- Best Team Costume Competition

We will also have one "Petite" heat where the teams consist of one adult and one child participant. The "Petite" heat will begin promptly at 11:00AM on the main stage with the adult heats starting right after the Petite's are done. We will have live music after the stomp from 3:00 - 6:00 PM.

** Any registrations after 8/15/26 will NOT be guaranteed a Grape Stomp T-shirt.

https://baileysrunvineyard.ticketspice.com/grape-stomp-2026