Event calendar
National Chocolate Day
Tuesday October 28th
Because life is better with chocolate!
11:00 AM - 06:00 PM
Spooktacular Wine-O-Bingo
Wednesday October 29th
Spooktacular Halloween Bingo Night!
Get ready for a hauntingly good time as we turn Bingo night into a fright fest! Join us for an evening filled with eerie excitement, creepy prizes, and a costume contest that’ll give you chills.
Come dressed to impress — we’ll be awarding prizes for best solo, duo and group costumes!
Enjoy wickedly good wine, plenty of laughs, and maybe a few ghostly surprises along the way.
It’s all fun and games until someone yells… BINGO!
CASH ONLY for bingo cards!
3 cards MAX per person
06:00 PM - 08:00 PM
Happy Halloween!
Friday October 31st
Dress to impress in your best costume and join us on Halloween weekend! We'll be decked out all weekend long and you should be too!
10:00 AM - 09:00 PM
Live Music feat. Richardson Acoustic
Friday October 31st
Richardson Acoustic playing October 31st 5-8PM!
05:00 PM - 08:00 PM
Live Music feat. Lake Collective
Saturday November 1st
Lake Collective, founded by Linell Muse, showcases fan-favorite covers performed either solo or alongside talented local musicians. A lifelong musician, Linell grew up in the church, where his love for music was first shaped. Originally a drummer who was encouraged to sing, he has since expanded into vocals, multiple instruments, and a style that blends soulful energy with heartfelt expression.
Through Lake Collective, Linell’s mission is to share joy, connection, and community through music—whether in intimate settings or larger gatherings.
02:00 PM - 05:00 PM
Live Music feat. Leah Brooke
Sunday November 2nd
Dark, bluesy, jazzy, pop-rock originals and a mix of irresistible covers delivered with a sprinkle of nerdy dry humor and a touch of awkward charismatic charm.
Midwestern singer-songwriter Leah Brooke is an indie producer/videographer for Lucky Tooth Records and an enigmatic performing artist bearing stripped-down, bare-bones electric guitar and soul-snatching vocals. Brooke often mixes electronic beats and soundscapes into her simple setup and likes to blend songs together into "the best mash-ups ever". Audiences can expect to hear songs spanning 7 decades including favorites as well as lesser-known deep cuts by everyone from The Beatles to The White Stripes, including Billy Holiday, The Strokes, Depeche Mode, The Doors, Dolly Parton, Johnny Cash, Dianna Ross, Neko Case, Elton John, and The Yeah Yeah Yeahs to name just a few. Brooke has toured from coast to coast and most recently enjoyed a summer-long residency at Door Peninsula Winery and a regular slot singing on the water with Sail Door County.
01:00 PM - 04:00 PM
Live Music feat. Noah Hittner
Friday November 7th
Despite being raised the son of a local Country-Rock legend, Noah procrastinated for well over three decades before finally picking up the guitar to begin the new year in 2009. Influenced by everything from folk-rock to hip-hop, Noah has recorded and released several albums which blend the singer-songwriter, acoustic, rock, urban, and electronic styles into a singular Acoustic-Tronic genre. This collage of influences creates a sound that begs listeners to feel something. Currently based out of Madison, WI and regularly touring the Midwest, Noah performs with the use of a looper pedal and various effects, creating a wildly entertaining, full-band sound.
05:00 PM - 08:00 PM
Live Music feat. Kylar Kuzio
Saturday November 8th
Born in West Virginia, Kylar moved several times while growing up, taking observations and experiences from each person and place she came to know. This can be seen in her songwriting which is highly personal yet universally applicable. She writes primarily for herself, processing life and all of the emotions that come with it, but ultimately her writing is for those who listen. It is her hope that listeners find something relatable & beautiful within her lyrics.
02:00 PM - 05:00 PM
Live Music feat. Taylor Schereck
Sunday November 9th
Taylor Schereck is an acoustic rock/pop singer from the Madison, WI area. Growing up in Mount Horeb, WI, music was always an integral part of his life. He was surrounded by musicians, including his father- a guitarist, his mother- a vocalist, his uncle Von- a drummer who he frequently performs with, and his grandfather- a guitarist and songwriter. He can also be seen with the Foo Foo Dolls, a 90's cover band, and The Remedy - another high energy band. Catch Taylor engaging his audiences throughout Southeast Wisconsin, as he brings his unique rock/pop style to the stage.
01:00 PM - 04:00 PM
Live Music feat. Shekinah King
Friday November 14th
Shekinah's powerhouse vocals will make you stop dead in your tracks. As even our owner has been quoted as saying "I could listen to her sing the phone book!" She's a musician you won't want to miss!
05:00 PM - 08:00 PM
Christmas
Thursday December 25th
Happy Holidays to all of our fans! We are CLOSED on Christmas Day.
11:00 AM - 06:00 PM
New Year's Eve
Wednesday December 31st
Celebrate the New Year with us and join us on New Year's Eve!
11:00 AM - 06:00 PM
Grape Stomp 2026
Saturday September 12th
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
11:00 AM - 03:00 PM