Saturdays are made for music and wine! 🎤🍷

Join us for live tunes by duo, Seth James & Kylar Kuzio, delicious pours, and all the good vibes your weekend needs.

Tag your crew — it’s time to sip, sing, and celebrate Saturday! ✨

Round out the Christkindli Market weekend in downtown New Glarus with some live music, delicious wine and amazing pizza at Bailey's Run!

Forget the mall madness — come Sip & Shop! 🎄🍷 Enjoy a glass of wine while browsing amazing local vendors for the perfect holiday gifts.

🍷 Wine by the glass & bottle specials 🎁 Unique, handcrafted gifts 🎶 Holiday music & plenty of cheer

Wrap up your shopping the fun way — with wine in hand! 🥂

Sip, Shop & Sing Along! 🎶🍷

Join us for our Sip & Shop Weekend — two days of holiday cheer, local shopping, and live music all weekend long!

🛍️ Shop from amazing local vendors

🎵 Enjoy live music while you sip your favorite wines

🍷 Seasonal wines and festive vibes all around

Bring your friends, grab a glass, and soak up the sounds of the season — it’s the perfect way to kick off your holiday shopping! ✨

Forget the mall madness — come Sip & Shop! 🎄🍷 Enjoy a glass of wine while browsing amazing local vendors for the perfect holiday gifts.

🍷 Wine by the glass & bottle specials 🎁 Unique, handcrafted gifts 🎶 Holiday music & plenty of cheer

Wrap up your shopping the fun way — with wine in hand! 🥂

Santa’s coming to town — and joining us for breakfast!

Bring the whole family for a morning filled with holiday cheer, delicious food, and a chance to meet the big guy himself. Stay and shop our local vendors in the event room with all their amazing products for those hard to shop for friends and family!

🥞 Enjoy a festive breakfast

🎅 Meet & take photos with Santa

🎨 Holiday crafts and fun for the kids

🛍️ Shop local vendors located in our event room

It’s the most magical morning of the season — don’t forget your wish list! ✨

We’re kicking off the season with a Sunday full of magic, music, and merriment! 🎅🍷🎶

🎅 Breakfast with Santa – Start your morning with a hearty breakfast, holiday cheer, and a special visit (and photos!) with Santa himself. Perfect for the whole family!

🛍️ Sip & Shop – After breakfast, browse local vendors and find the perfect holiday gifts while sipping your favorite wines.

🎵 Live Music – Enjoy rockin' tunes throughout the day from CT & The Breeze — to keep you moving while holiday shopping and sipping.

It’s time to dust off your most beautifully hideous holiday sweater and join us for a night of festive fun, wine, and Bingo! 🍷✨

🎅 Wear your best (or worst) holiday sweater — prizes for the ugliest!

🎁 Play a few jolly rounds of Bingo

🍷 Sip your favorite wines and enjoy plenty of holiday cheer

It’s going to be a holly jolly (and slightly tacky) good time! ❤️💚

Unwind and soak up the weekend vibes with live music every Saturday! 🎶

Enjoy beautiful tunes, local wine, and the perfect spot to relax with friends.

Good music, great wine, and golden-hour moments — see you Saturday!

He’s back! 🎸 Mark Croft returns to our stage for a solo performance you won’t want to miss.

Relax with a glass (or a mimosa 😉) and enjoy a Sunday filled with great music, good wine, and perfect vibes before Monday rolls around.

It’s the ultimate way to wrap up your weekend — with the man, the myth, the legend himself! 🍷🎶

🎄 Christmas Cookie & Wine Pairing 🍷🍪 ‘Tis the season for sweets, sips, and a little holiday cheer! ✨

Join us for a cozy afternoon of Christmas cookie and wine pairings, where each delicious bite is matched with the perfect pour. 🍷❤️

🎁 Limited spots available — grab your tickets now and treat yourself to the sweetest holiday experience of the season!

https://baileysrunvineyard.ticketspice.com/christmas-cookie-wine-pairing-2025

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

It’s our last Friday night of live music for a while, and we’re going out in style with James Crockett! 🎸🎶

We know the holidays can be hectic — so take a break, grab a glass, and unwind with great music, good company, and your favorite local winery. 🍷✨

Bring the whole family and make it a Friday to remember! ❤️

The holidays were for giving… now it’s time for treating yourself! 💃🍷

Come spend the afternoon with live music, amazing wine, and mouthwatering food. You’ve earned it! 😍🎶

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! 🍾🎶✨

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!

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

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. ❤️

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!

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. ❤️

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.

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! 🍇✨

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! 🍷✨

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.

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

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

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