Featuring Live Music Every Weekend, Year-Round!

Myles Dyad Duo2

Friday, July 23rd 5-8 pm - Live Music w/Myles Talbot Duo

We are a unique music experience – guy with a guitar…girl with a harmonica playing a continuously changing set list from the 70’s to today.  We take cover songs from artist’s like “Dylan”, “Petty”, “Jimmy Buffet”, “Billy Joel”, “Lumineers” and many, many others.  We use our own unique style enhancing them to keep your guests delightfully entertained, engaged while having an enjoyable music experience. 

Gary the Band2

Saturday, July 24th 3-6 pm - Live Music w/Gary The Band

Looking for a great time? These guys are a blast! Bring your friends, lawn chairs while enjoying a beautiful afternoon in New Glarus : )

Hoot Hollers3

Sunday, July 25th 3-6 pm - Live Music w/Hoot & Hollers

Bring your friends, lawn chairs while enjoying a beautiful afternoon in New Glarus : )

Wednesday, July 28th 6 pm - Bailey's Bingo Bash

Join us for Bailey’s Bingo Bash and have a blast with your friends, eating, drinking & winning!

Thursday, July 29th 6 pm - Learn How to Make Neapolitan Pizza!

Get your Tickets now for our Pizza 101 Class. You will learn about the history of Neapolitan pizza, the ingredients and how to make Neapolitan pizza. You will stretch your own dough, top your pizza and get to cook it in our authentic Italian brick oven. Includes appetizer and 2 Drink Tickets.

Get Tickets Here!

Saturday, July 31st 3-6 pm - Live Music w/Alpha Romeos

Hailing from Mount Horeb, WI – the Alpha Romeos are a quintet that brings tightly focused sets of clasic funk, R&B, soul and blues.  harmonica. Nurse by day, musician by night – Kurt believes in the healing power of music. 

Chasing Denver5

Sunday, Aug 1st 2-5 pm - Live Music w/Chasing Denver

Recently formed country music duo Chasing Denver sparks interest in all parts of the world with their strong blend of harmonies and love connection they share on and off stage.

Consisting of Chris and Victoria (formerly Smith) Kemp, these two artists started off individually, performing in two different parts of the country (New York and Ohio), and met in 2017 in Southwest Florida.
Since then, they’ve shared the stage with acts such as Thompson Square, Scotty McCreery, Michael Ray, Colt Ford, and more. Catch them in a city near you!
Duane Worden2

Friday, Aug 6th 5-8 pm - Live Music w/Duane Worden

Duane has been performing as a musician for over 40 years. He has toured with successful bands as well as showcasing his solo act. He has performed throughout the country as well as abroad having played piano bars in Cairns, Australia & busked in Auckland, New Zealand. His performances are custom tailored to each event from playing all acoustic shows to full concerts with guitar/keyboard accompaniment. Emphasis is always placed on his singing, however, whether it’s a cover song or an original. Duane focuses mostly on Light Rock from the 60’s & 70’s but can cater to specific settings. 

Gin Choc

Saturday, Aug 7th 3-6 pm - Live Music w/Gin, Chocolate & Bottle Rockets

Gin, Chocolate and Bottle Rockets is the Madison, WI based girls group, made up of Shawni Marks, Beth Kille and Jen Farley. 

Andy Yaun

Sunday, Aug 8th 2-5 pm - Live Music w/Andy Yaun

Andy Yaun is a local guitar slinger always in action as he sings and shreds his way through original and classic rockabilly tunes on a Gretsch Guitar.

Two County Lines2

Friday, Aug 13th 2-5 pm - Live Music w/Two County Lines

Enjoy Friday night with Two County Lines! Wine, Pizza, Beer & More!

Carper Diem

Saturday, Aug 14th 3-6 pm - Live Music w/Carper Diem

The Carper Diem Band puts a bluesy groove to their take of classics from B.B. King, Junior Parker, Buddy Guy and Junior Wells, Solomon Burke and a host of other great R&B artists past and present. 

Sunday, Aug 15th 2-5 pm - Live Music w/King Sies Fries

Kick back on a Sunday afternoon with King Sies Fries. 

James Crockett6

Friday, Aug 20th 5-8 pm - Live Music w/James Crockett

James grew up in East Madison and Deerfield, WI. And has always had a passion for music. Early influences were wide-ranging and inlcude Elvis, James Taylor, Frank Sinatra, KISS, The Outlaws, Elton John, The Stones, The Beatles, Springsteen and John Denver. Today he is currently doing what he’s always dreamed of doing; performing tunes by artists he’s been inspired by and doing tunes that people know and love. 

Dawg Bones

Saturday, Aug 21st 3-6 pm - Live Music w/The Dawg Bones

The Dawg Bones bring the Blues for a jammin Saturday afternoon. Bring your lawn chairs and friends and groove out.

Top Shelf5

Sunday, Aug 22nd 2-5 pm - Live Music w/Top Shelf

Versatility and variety! Great tunes from all eras with a healthy “pour” of ’70 & ’80s rock and pop. Expect surprises! Award winning musicians performing well-crafted arrangements with a full sound but a small footprint.

Amelia Ford

Friday, Aug 27 5-8 pm - Live Music w/Amelia Ford

Amelia is a Singer-Songwriter featuring Folk, Rock & Alternative music. 

aug 28 2021

Friday, Aug 28 3-6pm - Live Music w/Mark Croft Band

A singer/songwriter and acoustic guitarist with Roots, Rock, & Americana song styling, Mark Croft is the classic ‘triple threat’; a skilled guitar player, a powerful and dynamic vocalist, and a talented songwriter and entertainer.

Kirstir Kraus2

Friday Aug 29, 2-5pm - Live Music w/Kirstie Kraus

Three years ago, the Wisconsin native made the move to Music City and having heavily toured the summer before with her Midwest band, Thirsty Jones, Kirstie made the decision to really focus on honing her craft in town. She immediately began demoing out songs for her upcoming full length record and playing established Nashville venues, like the Listening Room Café and the Bluebird. She also leaned into the production side of her album, gaining great insight from her then producer about arrangements, vocal styling, and mixing. Her first Nashville based single, “Delusional” (2018) fancies a sassy 80s funk groove while 2019’s “Gotta Do” pulls in early 2000s Shania vibes. “Silver”, her July 2020 release, possesses the licks of Joan Jett and attitude of Avril Lavigne, proving that she’s not a one lane roadmap.



Saturday Sept 4, starting @11 am - 2nd Annual Grape Stomp

Join us for our 2nd Annual Grape Stomp at Bailey’s Run Vineyard & Winery!

Everyone who plans to stomp must pre-purchase tickets online. A Team consists of 2 people; one who stomps the grapes and the other gathers the juice. The Team who produces a specific amount of juice the fastest will be the winner. The registration fee includes the stomping competition, commemorative T-Shirt per team member and a drink ticket 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.

Following all competitive stomping heats we will have:

– Best Team Costume Competition

We will also have a “Petite” competition where the Team consists of one adult and one child participant, the child must stomp. Petite competition begins at 11 AM with adult heats starting at noon. Purchase Tickets Here!