Kivy & Pray

Saturday, Oct. 12th @ 2-5 PM

Kivi & Pray are two Wisconsin songwriters who perform, record, and travel together. Over eight years and 10,000 miles on the road, Thomas Kivi and Sarah Pray have blended their influences together into a fresh, honest blend of Americana

Autumn Acoustic

Saturday, Oct. 19th @ 2-5 PM

Some folks wished we would play Bailey’s Run and now we are. Perhaps next they could wish us winning the lottery? Come spend an autumn afternoon bebopping in a beautiful setting near New Glarus! What a great time of year to be in Wisconsin.

Kenny Curtis

Saturday, Oct. 26th @ 2-5 PM

Come out to the winery for some live Classic Rock by Ken Curtis! You can’t go wrong with fantastic Wisconsin crafted wine and live music!

Decadent Delights - Wine & Tapas Pairing Event

Sunday, Oct. 27th @ 3 PM

Mark your calendars for an exclusive wine & tapas pairing event. Let us lead your through a tasting of Bailey’s Run wine with a selection of food items freshly prepared by Chef Colleen! Click Here for More Info & Tickets!

Wine-O-Bingo (Halloween Edition)

Thursday, Oct 31st @ 6 PM

Just when you thought our Bingo nights couldn’t get any more amazing…we throw in a kick butt costume contest as well! Dress to impress as our tasting bar staff will be judging your costumes throughout the night. We’ll have a 1st and 2nd place for Single, Doubles and Group categories.

Not to mention winning amazing prizes during Bingo we’ll also have some spook-tacular food for you as well! Don’t miss out!

Erin Krebs

Saturday, Nov. 2nd, 2-5 PM

Come out to the winery for soulful, jazz, blues, wine & food!

80's Movie Trivia Night (Benefitting the Ben Jackson Foundation)

Friday, Nov. 8th, 6 PM

Think you know movies from the 80’s better than anyone? Put your knowledge to the test while supporting a cause! The Ben Jackson Foundation and Bailey’s Run Vineyard and are teaming up again Friday, November 8, in honor of Veteran’s Day.

The evening will be packed with fun for all ages; trivia for anyone who enjoys classic films such as Ferris Bueller’s Day Off, The Goonies, and Back to the Future. There will be wine for those 21 years and older, and a table for making card to send to veterans in honor of Veterans Day!

Show your support for our military personnel, both newly enlisted and those long retired by joining us and Bailey’s Run Vineyard for a fun-filled night!

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