Event calendar
LIVE MUSIC w/Britton & Sarah
Friday August 7th
Wisconsin-based musical duo featuring instrumentalist/vocalist Britton Rea & vocalist Sarah Krahn.
05:00 PM - 08:00 PM
LIVE MUSC w/Gin Mill Hollow
Saturday August 8th
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.
03:00 PM - 06:00 PM
LIVE MUSIC w/The Dawg Bones
Sunday August 9th
This is American music, back to basics with a three piece band playing early Rock-'n-Roll,
02:00 PM - 05:00 PM
National Red Wine Day
Friday August 28th
It's National Red Wine Day! Come enjoy a glass from our excellent selection!
11:00 AM - 09:00 PM
Live Music feat. Chasing Denver (TICKETS REQUIRED)
Sunday September 6th
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
03:00 PM - 06:00 PM
Labor Day
Monday September 7th
Come celebrate the long Labor Day weekend with us!
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
National Chocolate Day
Wednesday October 28th
Because life is better with chocolate!
11:00 AM - 05:00 PM
Halloween
Saturday October 31st
Bring your best costume and join us on Halloween!
11:00 AM - 09:00 PM