Event calendar

Live Music feat. Matt Jaye

Sunday December 28th

We’re counting down to a brand-new year! 🎉

Celebrate the final Sunday of 2025 with live music by Matt Jaye, great wine, and all the good vibes.

Stop in, grab some champagne to toast the New Year, and enjoy an afternoon of local music and celebration! 🍾🎶✨

01:00 PM - 04:00 PM

New Year's Eve

Wednesday December 31st

Celebrate the New Year with us and join us on New Year's Eve! We will have our New Year's Eve Open House with live music and specials all day!

10:00 AM - 08:00 PM

Live Music feat. Mark Croft

Wednesday December 31st

Live music + wine + New Year’s vibes = the perfect night! 🎉 Join us New Year’s Eve for a night of music, toasts, and memories. 🥂🎶

04:00 PM - 07:00 PM

Live Music feat. David Hecht

Saturday January 3rd

Warm up your weekend with great wine, good company, and live tunes from your favorite local artist - David Hecht from 2-5PM!

02:00 PM - 05:00 PM

Live Music feat. Shekinah King

Sunday January 4th

Cold outside? We’ve got the cure — live music feat. Shekinah King from 1-4PM!

Join us for cozy vibes, great tunes, and your favorite pours all day long. ❤️

01:00 PM - 04:00 PM

Live Music feat. Jason Thomas Band

Saturday January 10th

Join us Saturday, January 10th from 2-5PM for live music feat. The Jason Thomas Band, local wine, and all the cozy vibes you need this winter. 🍷🧣

Grab your friends, grab a glass, and make your weekend plans with us!

02:00 PM - 05:00 PM

Live Music feat. Seth James

Sunday January 11th

Sundays are for slowing down, sipping wine, and soaking up some great music! Join us for a relaxing afternoon featuring live music by Seth James from 1-4PM. Pair your favorite glass with great tunes and good company — the perfect way to end the weekend. ❤️

01:00 PM - 04:00 PM

Live Music feat. Taylor Schereck

Saturday January 17th

Sip, sway, and soak in the Saturday vibes! 🎶🍷 Join us for live music with Taylor Schereck Saturday, January 17th from 2-5PM — because weekends are better with wine and a soundtrack.

02:00 PM - 05:00 PM

Live Music feat. Jesse Bauman

Sunday January 18th

Let’s turn your lazy Sunday into a lively one! 🎶🍷 Join us for Sunday Live Music with Jesse Bauman, great wine, and the best vibes around.

Grab a glass, grab your friends, and let’s wrap up the weekend the right way! 🍇✨

01:00 PM - 04:00 PM

Live Music feat. Moon Gypsies

Saturday January 24th

It’s Saturday — and that means live music at Bailey's Run! 🎶🍇 Unwind with a glass (or two) of your favorite wine while The Moon Gypsies sets the mood for a perfect evening.

The wine’s flowing, the music’s playing, and all that’s missing is you! 🍷✨

02:00 PM - 05:00 PM

Live Music feat. Mark Croft

Saturday January 31st

Delicious wine, cozy vibes, and live tunes — that’s how we do Saturdays! ❄️🍷🎶 Join us for Mark Croft, grab a glass, and let the music take over your weekend.

02:00 PM - 05:00 PM

Live Music feat. Markus J

Sunday February 1st

Sips + Sounds = Sunday perfection. 🍷🎶 Join us for live music with Markus J— good tunes, great wine, and even better company! ❤️

01:00 PM - 04:00 PM

Valentine's Day

Saturday February 14th

Join us on Valentine's Day for the perfect romantic day out!

11:00 AM - 09:00 PM

St. Patrick's Day

Tuesday March 17th

Grab your best green garb and join us for St. Patrick's Day!

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

Location

N8523 Klitzke Road
New Glarus, WI
53574

Hours

Mon, Tue, Wed, Thur
11:00 AM - 5:00 PM
Fri
10:00 AM - 6:00 PM
Sat
10:00 AM - 8:00 PM
Sun
10:00 AM - 5:00 PM