Halloween night · Saturday, October 31 · Doors 6 PM · 21+
The Witches Ball
Professor Pinkerton’s Dead Man’s Carnival: theatre, magic, live music, a banquet-style feast, tarot and a costume contest, at reserved tables in the barn.
Online ticket sales die in…
Live Music, Good Company, and Kettle Moraine Charm.
Yacht Secrets
October 29, 2026 | 7:00 pm - 10:00 pm Saloon
⛵️🚨 ALL ABOARD THE YACHT! 🚨⛵️
Yacht Secrets is setting sail on October 29th from 7–10 PM! 😎🎶
Familiar strangers from parts unknown, boldly going where other yacht rock musicians dare to go.
Throw and go. Practice? Hell no. 😂
You never know what’s going to happen… and honestly, neither do they. That’s what makes Yacht Secrets the most organic yacht rock experience of your damn life.
Smooth grooves. Big vibes. Questionable decisions. And plenty of surprises. 🕶️🌊🍹
📅 Thursday, October 29th
⏰ 7–10 PM
📍 Jennings Holler — Eagle, WI
🎟️ No cover charge
Yacht Secrets — come aboard and see what happens! ⛵️🔥
Witches Ball
October 31, 2026 | 6:00 pm - 11:00 pm Buckhorn Barn
THE WITCHES BALL
Halloween Night • October 31st, 2026
6 pm – Doors, Cocktail hour and Appetizers, Dinner, Atmospheric Ambient Entertainment
7 pm – Act One
Intermission
8:30 pm Act Two-
featuring “Quintet du hot club de France”)
Intermission
10 pm Act Three
11pm – Finale
Some shows you can explain.
This one… we honestly don’t know how.
Professor Pinkerton’s Dead Man’s Carnival is bringing an experience to Jennings Holler that is part theatrical performance, part magic, part musical spectacle—and something entirely its own.
It’s insane.
It’s immersive.
It’s strange.
And it’s something you simply have to experience for yourself.
Expect an evening of:
• Immersive theatrical performances
• Live musical performances
• Magic
• Banquet-style feast
• Tarot readings
• Costume contest
• Reserved table seating
• And things we probably shouldn’t even try to explain.
21+ ONLY
Dress fancy. Come as a mythical creature, character, witch, beast, fae, or whatever strange thing you can dream up.
TICKETS ARE SOLD ONLINE ONLY. NO TICKETS AT THE GATE.
October 31st.
Jennings Holler.
The Witches Ball awaits.
THE BARRED OWL STRING BAND
November 1, 2026 @ 2:00 pm - December 1, 2026 @ 5:00 pm Saloon
🍂🎻 BLUEGRASS STEW SUNDAY IS CALLING! 🦉
As we roll into winter, we’re bringing the good folks together, warming up the saloon, and keeping our Sunday tradition alive with a little pickin’, a little grinnin’, and a whole lot of good ol’ bluegrass!
We’re mighty happy to welcome BARRED OWL STRING BAND back to Jennings Holler! ❤️🪕 These fine folks know how to fill a room with the sounds of bluegrass, and there ain’t no better way to spend a Sunday afternoon than gathered around good music and good company.
📅 Sunday, November 1st
⏰ 2 PM – 5 PM
🎟️ NO COVER CHARGE!
📍 Jennings Holler — Eagle, Wisconsin
So grab your friends, shake off that November chill, and come get cozy with us in the saloon. The days may be getting colder, but the music’s still mighty warm down here in the Holler!
Come hungry for music, thirsty for good company, and ready for a down-home Sunday! 🤠🎶
#BluegrassStewSunday #JenningsHoller #BarredOwlStringBand #LiveBluegrass #SupportLiveMusic
JASS HAMS
November 7, 2026 | 7:00 pm - 10:00 pm Saloon
Jazz Hams ARE COMING TO THE HOLLER!
Get ready for a night of live music, good company, and good times at Jennings Holler!
Join us Saturday, November 7th as Jazz Hams take over the Saloon Stage for a night of live music!
LIVE MUSIC | NO COVER CHARGE
WHEN: Saturday, November 7th
TIME: 7–10 PM
WHERE: Jennings Holler Saloon Stage
ADDRESS: W379 S9674 County Road S, Eagle, WI
Bring your friends, grab a drink, and settle in for a Saturday night at the Holler. The music is free, the saloon is waiting, and there’s always room for a few more!
See y’all at the Holler!
Sean McKee Band
November 14, 2026 | 7:00 pm - 10:00 pm Saloon
🔥 THE Sean McKee Band IS COMING BACK TO JENNINGS HOLLER! 🔥
Remember their late-night Saloon set at Wave That Flag? We just had to have them back.
If you like The Allman Brothers Band, Derek Trucks, Widespread Panic, Tedeschi Trucks Band, JJ Cale, and that jazz-at-the-crossroads kind of energy…
You’re going to fall in love with this band.
Originals & Tasteful covers!
Expect soulful guitar work, deep grooves, improvisation, and musicians who know how to let a song breathe and take it somewhere unexpected.
📅 November 14th
⏰ 7–10 PM
📍 Jennings Holler
W965 S9674 County Rd S Eagle, WI
🎸 Sean McKee Band
💰 NO COVER
Mark your calendars.
We saw what they did with that late-night Saloon crowd at Wave That Flag…
We just had to bring them back. 1
Holler Open Jam Night
November 18, 2026 | 6:00 pm - 10:00 pm Saloon
🎸🔥 HOLLER OPEN JAM! 🔥🎸
Every 3rd Thursday of the month, we’re opening up the stage and calling ALL MUSICIANS!
🎶 Bands • Singer-Songwriters • Solo Musicians
🥁 Drum kit provided
🎤 Pro sound
🎸 Instruments of all sorts
🍕 Food truck on-site + pizza inside
💰 NO COVER CHARGE
📝 Sign up in person at 6 PM
🎵 Jam starts at 7 PM
Come play, come listen, or just come hang out. Bring your instrument, bring your friends, and make some noise at the Holler!
📍 Jennings Holler — Eagle, WI
Hosted by Party Marty 🎸🤘
German Bluegrass Christmas Market
December 5, 2026 | 9:00 am - 11:00 pm Buckhorn Barn
A Bluegrass German Christmas Market at Jennings Holler, Eagle WI — Saturday, December 5. Makers market opens at 9 AM, music from 11 AM to 11 PM. German food, Santa & Mrs. Claus, hot toddies and so much more!Hosted by Chicken Wire Empire and Armchair Boogie, with Art Stevenson & Highwater, High & Rising, Bigtooth, Sheilagh Dandelyon & Billy Bronsted, Piper Road String Band, Valley Fox, Luke Cerny & Ryan Ogburn.Tickets: Early Bird $30 through October 31 · $40 from November 1.
Jennings Holler is a one-of-a-kind destination venue in Eagle, Wisconsin, built for music, community, celebration, and unforgettable experiences. Nestled in the Kettle Moraine region, Jennings Holler hosts hundreds of events each year, drawing locals and travelers alike for live music, festivals, bike nights, private gatherings, and seasonal celebrations.
At the heart of the property is the Jackass Saloon, a high-energy live music bar known for packed dance floors, winter-proof crowds, and an always-welcoming vibe. Just steps away, the Buckhorn Barn offers a versatile, rustic space ideal for weddings, large receptions, private parties, workshops, and community events. Completing the grounds is the Saint Rose Chapel, a serene and intimate setting perfect for ceremonies, vow renewals, spiritual gatherings, and meaningful moments.
With expansive grounds, flexible indoor and outdoor spaces, and a strong focus on supporting local artists, vendors, and small businesses, Jennings Holler is more than a venue—it’s a destination where people come together to celebrate music, culture, and connection year-round.
