LIVE MUSIC - Ryan Casey

Saturday, Sept. 14th @ 2-5 PM

Taking inspiration from soul great Martin Sexton, singer-songwriter Ryan Adams and folk legend James Taylor, Ryan Casey directs his music with a spirit and presence rooted in tradition. This unique brand of adult alternative music aims to inspire listeners.

Come on out and enjoy some amazing music, delicious food and as always fantastic wine!

Czars's Promise - Drink Wine - Fight Cancer.

Saturday, Sept. 14th @ 1-4 PM

Join Czar’s Promise on Saturday, September 14 from 1-4 pm at Bailey’s Run Vineyard to drink wine and fight cancer!

$1 from every glass of wine purchased will be donated to Czar’s Promise. to help fight canine and pediatric cancer and help support those who have received a diagnosis in our community.

Come enjoy great company, community partners, live music, raffles, and food and drink! Well-behaved, leashed dogs are welcome outside on the lawn and patio.

LIVE MUSIC - Dan Brusky

Sunday, Sept. 15th @ 2-5 PM

Local guitarist and vocalist, Dan Brusky, has been entertaining audiences for over 20 years with his unique interpretations of songs.

Come out to your favorite local winery for a day of live music, food and wine!

LIVE MUSIC - Alpha Romeos

Saturday, Sept. 21st @ 2-5 PM

Based out of Mount Horeb, Wisconsin, Alpha Romeos quintet brings blues, R&B, funk and classic soul covers. Drummer Chris Morkri along with bassist Stan Gregory whip up a tasty groove cake. Keyboardist Jeff Ingbritsen and guitarist Tom Heaney bring on the frosting with rambunctious chords and tasty leads. Lead singer Shekinah King brings light to sound with her sweet vocal range. Together, Alpha Romeos makes desert the main course.

Signs by Caitlin

Wednesday, Sept. 25th @ 6 PM

Grab a friend or two and join us for a DIY Wood Sign Workshop at Bailey’s Run Vineyard! Signs by Caitlin offers over 250 design options. Come have a glass of wine or share a bottle and spend a fun evening with us! Registration is required.

The Krause Family Trio

Saturday, Sept. 28th @ 3-6 PM

The Krause Family Band is an Americana band known for it’s organic sound and close family harmonies.

Gary the Band

Sunday, Sept. 29th @ 2-5 PM

Acoustic trio, Gary, showcases the musical talents of Marques Johnson, Josh Calhoun and Brian Matteson. Formed in 2012, Gary brings a unique sound to the Southern Wisconsin area, basing their approach on vocal harmonies and tasteful guitar work. With all members of the band sharing the duties of vocals, guitar, and percussion, Gary is able to play a diverse selection of music including classic and modern Pop, Rock, Folk and more. Combining individual studio albums with years of performing and touring experience, each member adds their own flavor to the group


Saturday, Oct. 5th @ 2-5 PM

Back2Back is an acoustic duo performing a variety of styles with guitar and vocals in close harmony.

Kivy & Pray

Saturday, Oct. 12th @ 2-5 PM

Kivi & Pray are two Wisconsin songwriters who perform, record, and travel together. Over eight years and 10,000 miles on the road, Thomas Kivi and Sarah Pray have blended their influences together into a fresh, honest blend of Americana

aAutumn Acoustic

Saturday, Oct. 19th @ 2-5 PM

Some folks wished we would play Bailey’s Run and now we are. Perhaps next they could wish us winning the lottery? Come spend an autumn afternoon bebopping in a beautiful setting near New Glarus! What a great time of year to be in Wisconsin.

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