It's time for one last cheers to fall! Join us for Harvest Sips Bingo, where the wine is flowing, the prizes are fun and the laughter never ends!

Sip your favorite wines while playing a few spirited rounds of bingo. Win awesome prizes and enjoy a cozy evening with friends. Bring your lucky charm - and maybe your competitive side!

Let's raise a glass to good wine, good company and a little friendly competition.

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!

High energy, fun duo with years of experience performing. Recently formed in 2023 and have had lots of fun ever since! They play a variety of Modern & Classic Country, as well as some Pop and Rock in Southern Wisconsin & Northern Illinois!

The Artesian's are back at the Bailey's Run stage with some amazing low-key music sure to keep you tapping your feet to the beat!

Back by popular demand we will be offering a wine & pie pairing experience! This is a limited seating event that is sure to please. We will have five scrumptious pies expertly paired with our wines so you can take your newly found expertise to all of your holiday excursions! 

**Some pies may contain allergens so please contact us in advance if you have any allergies we will need to be aware of.

https://baileysrunvineyard.ticketspice.com/november-pie-pour-pairing

From Classic Rock, to Country, with some oldies and one hit wonders thrown in, you will hear a little bit of everything when you join Steve Weber for some music and fun. Steve's roots are in rock & roll and over the years he has performed with a couple southern Wisconsin bands, but now days he enjoys brining some rockin' solo acoustic music to area establishments.

Katie Scullin is an award-winning singer and songwriter who has captivated audiences at festivals, listening rooms, and private parties all the way from Northern Wisconsin to the heart of Texas country. Whether performing solo or backed by her band, Katie’s sound pulls from the influences of pop, rock, and soul, tied together by her signature rhythm guitar, broad vocal range, and newly infused keys.

Happy Holidays to all of our fans! We are CLOSED on Christmas Day.

Celebrate the New Year with us and join us on New Year's Eve!

Best. Day. Ever. Join us for National Pizza Day February 9th !

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