Jackass Saloon
The Jackass Saloon at Jennings Holler is where live music, cold drinks, and good times come together. With live bands almost every weekend, a full bar, tasty bar food, and a welcoming, down-to-earth vibe, it’s the perfect place to kick back, catch a show, and enjoy the night with great people and great sound.
LIVE MUSIC CALENDAR
3rd Annual SKORR Public Meeting
April 23, 2026 | 4:00 pm - 9:00 pmWe’re excited to announce that we will be having our 3rd annual SKORR meeting at Jennings Holler in the Jackass Saloon! Jennings Holler is located on Hwy S just east of Emma Carlin. They are relatively new to the area but are highly committed to getting involved in community and we look forward to getting more involved with them.
Save the date and keep your eyes peeled for more information in the coming weeks and months.
Looking forward to seeing all who can join us.
Pete Jive Featuring Brandon Riesdorf
April 24, 2026 | 7:00 pm - 10:00 pm🎻 Pete Jive featuring Brandon Riesdorf – Live at Jennings Holler 🎶
Get ready for a night of feel-good folk music that hits you right in the soul. Pete Jive featuring Brandon Riesdorf brings a blend of fiddle, guitar, and easygoing energy that’s perfect for kicking back, sharing a drink, and letting the music carry you.
This is the kind of sound that feels like home—lively enough to get your feet moving, smooth enough to sit back and take it all in.
📅 April 24th
⏰ 7PM – 10PM
📍 Jackass Saloon Stage – Jennings Holler
W379 S9674, County Rd S, Eagle, WI
🎟 No Cover Charge
Good tunes. Good people. No excuses.
Come out and catch a night that just feels right.
Fairy Succulents
April 25, 2026 | 12:00 pm - 2:00 pmFarmlands Showcase Co-op Pop Up
April 25, 2026 | 8:00 pm - 12:00 amFarmLands Friends and Family!!
We’re excited to preview our 2026 venue with a spring Co-op pop-up! Come out on April 25th for a free pop-up event at Jennings Holler in Eagle, WI.
We’ll be doing raffles, silent auctions, and door prizes, and we’ll have bumpin’ tunes all night!
Lineup DJs
Jezter
Plead the Filth
Clooless
Stikman B2B Mad Hazzard
GORG
Farm House
CO-OP POP UP
presented by Farmer Bob
8pm – 12am
door prizes etc.
W379 S9674, County Rd S, Eagle, WI 53119
Bluegrass Stew Sunday - Old Time Nouveau
April 26, 2026 | 12:00 pm - 5:00 pm🎻🔥 Bluegrass Stew Sunday at Jennings Holler 🔥🎻
There’s nothing like a Sunday at the Holler—good food, real music, and a community that knows how to kick back and enjoy the day.
Join us on SUNDAYS from 12–5 PM at the Jennings Holler – Jackass Saloon for Bluegrass Stew Sunday, featuring the soulful sounds, Old Time Nouveau.
Expect rich harmonies, driving acoustic rhythms, and that down-home bluegrass energy that hits just right.
🍲 Food by Pickets Country Store
Serving up hearty, feel-good favorites to keep you fueled while the music rolls on.
Whether you’re posted up with a drink, stomping your boots, or just soaking in the sound this is what Sundays were meant for.
Details:
• Food starts at 12 PM
• Music from 2–5 PM
• No cover charge
• Stick around until 7 PM to keep the party going!
📍 Eagle, Wisconsin
olive.you at the jackass Saloon
May 1, 2026 | 7:00 pm - 10:00 pmolive.you – Live at Jennings Holler
No Cover Charge
Settle in for an evening of heartfelt Americana folk with olive.you, a duo rooted in love, tradition, and songs that linger long after the last chord fades.
Blending warm harmonies, acoustic strings, and late-night honesty, olive.you brings music that feels worn-in, familiar, and quietly new. Their sound is shaped by commitment, shared values, and a deep belief in love that lasts — the kind you feel more than you hear.
Join us at the Jackass Saloon Stage for an intimate, easy-going night of live music, good company, and genuine connection.
🕖 7–10 PM
🎟️ No Cover Charge
📍 Jennings Holler – Eagle, WI
Come early, grab a drink, and stay awhile.
Craft Cocktail Workshop with Robyn
May 2, 2026 | 3:00 pm - 5:00 pmStep into the fresh air and celebrate the season at Jennings Holler with a hands-on outdoor experience you won’t forget 🌿🍸
Join us for a Craft Cocktail Workshop led by Chef Robyn, our in-house beverage guru, where you’ll learn how to mix, shake, and garnish your way into summer. Set against the natural beauty of the Holler, this open-air workshop is all about good vibes, fresh ingredients, and mastering those fancy cocktails you love.
For just $40, you’ll enjoy 6 handcrafted drinks while learning the skills behind each one—from flavor balancing to presentation. Whether you’re looking to impress at your next gathering or just want a fun afternoon outdoors, this workshop is the perfect way to sip, learn, and connect.
📍 Jennings Holler
W379 S9674 County Rd S, Eagle, WI
🎟️ Tickets available now at JenningsHoller.com
Come raise a glass with us and toast to warmer days ahead ☀️
Wise Jennings wsg/ Between Howls
May 2, 2026 | 7:00 pm - 10:00 pmFrom humble roots to a full-blown sound — Wise Jennings is back at the Holler 🎶🔥
What started as an Americana duo has grown into something much bigger. Wise Jennings, the creators of Jennings Holler, have evolved into a full band while staying true to their soulful, storytelling roots. Their sound still carries that raw, heartfelt Americana feel — just louder, richer, and built to move a crowd.
Now they’re bringing that energy home, and they’re not coming alone…
Joining them are special guests Between Howls, adding their own powerful edge to a night that’s all about community, connection, and unforgettable live music.
📅 May 2nd⏰ 7PM – 10PM📍 Jennings HollerW379 S9674 County Rd S, Eagle, WI🎟 No cover charge
Come experience the evolution of a band that helped build this place — and the music family that continues to grow around it.
This is more than a show… it’s the Holler way.
Bluegrass Stew Sunday - Aiden Muse
May 3, 2026 | 12:00 pm - 5:00 pm🎻🔥 Bluegrass Stew Sunday at Jennings Holler 🔥🎻
There’s nothing like a Sunday at the Holler—good food, real music, and a community that knows how to kick back and enjoy the day.
Join us May 3rd from 2–5 PM at the Jennings Holler – Jackass Saloon for Bluegrass Stew Sunday, featuring the 13 YEAR OLD Wisconsin homegrown AIDEN MUSE & FRIENDS
Expect rich harmonies, driving BANJO, and that down-home bluegrass energy that hits just right.
🍲 Food by Clark Street Food
Serving up hearty, feel-good favorites to keep you fueled while the music rolls on.
Whether you’re posted up with a drink, stomping your boots, or just soaking in the sound—this is what Sundays were meant for.
Details:
• Food starts at 12 PM
• Music from 2–5 PM
• No cover charge
• Stick around until 7 PM to keep the party going!
📍 Eagle, Wisconsin
The Big Kick Start - Bike Night 2026
May 7, 2026 | 3:00 pm - 11:00 pm……………………………Announcement…………………………..
🏍️ CALLING ALL BIKERS, CLUBS & ENTHUSIASTS! 🏍️
🎵 This is your party 🎵
Fire up those engines and ride on over to Jennings Holler for Jackass Saloon Bike Night — kicking off with a BIG KICK-START on May 7th, 2026 and rolling on every Thursday night until September.
This is your weekly home base for bikes, community, and live music all summer long. Whether you ride solo, roll deep with your club, or just love the Biker culture, Thursday nights are built for you.
🏍️ Bikes filling the Holler
🎸 Live Music
🍔 Food Trucks & Vendors
🚫 No Cover Charge
🕒 3pm – 11pm
📍 Jennings Holler – Jackass Saloon
W379 S9674, County Rd S, Eagle, WI 53119
Clubs, crews, and riders of all kinds — bring your colors, bring your people, and help us launch a season that’s loud, welcoming, and unforgettable.
👉 Big Kick-Start: May 7th
👉 Every Thursday until September
👉 More bands, themes & surprises TBA 🔥
Left Lane Cruiser
May 8, 2026 | 7:00 pm - 10:00 pmBAMM Trio at The Jackass Saloon
May 8, 2026 | 7:00 pm - 10:00 pm🎶 Catch the triumphant return of the BAMM Trio to the Jackass Saloon at Jennings Holler! 🎶
If you were there last time, you already know.
If you missed it, now’s your chance.
The BAMM Trio delivers a high-energy blend of blues, folk, funk, southern rock, and pure good-time grooves that fill the room and keep the night moving. Expect soulful riffs, tight rhythms, and a whole lot of fun.
🔥 Live on the Jackass Saloon stage at Jennings Holler 🔥
📅 February 13th
⏰ 7–10 PM
📍 W379 S9674 S, Eagle, WI
Come early, grab a drink, and settle in for a night of incredible live music, community vibes, and classic Jennings Holler energy.
🎸 BAMM Trio rocking the Jackass Saloon stage
Good music. Great people. One hell of a night 🍻
John Till
May 9, 2026 | 7:00 pm - 10:00 pm🎶 Jennings Holler Presents: John Till 🎶
Get ready for a night of soul-soaked sound and storytelling as John Till brings his bluesy roots and folk-driven songwriting to the Holler. With a voice that carries grit and heart, and guitar work steeped in tradition, John blends raw blues influence with the honest spirit of folk music, creating a sound that feels both timeless and deeply personal.
With that kick box and bottle neckslide guitar.
His songs echo backroads, late nights, and lived-in stories perfectly suited for an intimate evening under the Holler star lit sky!
Whether you’re a fan of stripped-down acoustic sets or rich, roots-inspired melodies, this is one you won’t want to miss.
🗓 May 9th
⏰ 7–10 PM
💥 No Cover Charge
Mother's Day Extravaganza
May 10, 2026 | 11:00 am - 3:00 pm🌸 Mother’s Day Extravaganza with Bryant’s on the Round 🌸
Treat the amazing moms in your life to a day full of love, flavor, and good vibes 💐
🍽️ All-You-Can-Eat Buffet | 11AM–3PM
Indulge in a massive spread featuring:
✨ Omelet station
🧇 Fresh waffles
🥐 Biscuits & gravy
🥗 Garden salad
…and so much more!
$40 per person
🍹 50% OFF Drinks for ALL Moms | 11AM–5PM
Because moms deserve to sip and celebrate all day long 🥂
🎶 LIVE BLUEGRASS MUSIC | 2–5PM
Hosted by Luke Cerny
FREE show — no cover, just good tunes and great company
🌼 BUT WAIT… THERE’S MORE!
Geske’s Gardens is bringing the beauty 🌿
🪴 Build-Your-Own Hanging Planter Basket Class starting at 12PM
Create a custom flower-filled basket for yourself or the moms you love
$40 per class
Make it a full day of food, music, flowers, and celebration 💛
Bring the family, bring your appetite, and let’s celebrate MOM the right way
Bike Night - 20 Watt Tombstone
May 14, 2026 | 3:00 pm - 11:00 pm🏍️ CALLING ALL BIKERS, CLUBS & ENTHUSIASTS! 🏍️
🎵 This is your party 🎵
Fire up those engines and ride on over to Jennings Holler for Jackass Saloon Bike Night With 20 WATT TOMBSTONE, 2026 and rolling on every Thursday night until September.
This is your weekly home base for bikes, community, and live music all summer long. Whether you ride solo, roll deep with your club, or just love the Biker culture, Thursday nights are built for you.
🏍️ Bikes filling the Holler
🎸 Live Music by Smooth Blues Band
🍔 Food Trucks & Vendors TBA
🚫 No Cover Charge
May 14th
🕒 3pm – 11pm
MUSIC STARTS AT 6PM
📍 Jennings Holler – Jackass Saloon
W379 S9674, County Rd S, Eagle, WI 53119
Clubs, crews, and riders of all kinds — bring your colors, bring your people, and help us launch a season that’s loud, welcoming, and unforgettable.
Indigo Canyon
May 16, 2026 | 7:00 pm - 10:00 pmJennings Holler Presents: Indigo Canyon
Get ready for a Saturday night filled with soulful sound, covers and original jam genre-blending vibes, and pure Holler magic. Indigo Canyon is bringing their signature energy to the Jackass Saloon Stage for a night you won’t want to miss.
🗓 Saturday, May 16th
⏰ 7PM – 10PM
🎟 NO COVER CHARGE
Come out to Jennings Holler and experience live music in a space that’s all about community, creativity, and good times. Whether you’re kicking back with a drink, dancing under the lights, or just soaking in the atmosphere,this is your Saturday plan.
Bike Night - Jackass Open Jam by Party Marty
May 21, 2026 | 3:00 pm - 7:00 pm🔥 BIKE NIGHT AT JENNINGS HOLLER 🔥
Rev it up and ride out to the heart of the Kettle Moraine State Forest for one of the wildest weekly meetups around… Bike Night at Jennings Holler 🏍️
Every Thursday, we’re calling all clubs, nomads, and motorcycle enthusiasts to roll in, kick back, and party with us under the pines. Whether you’re riding solo or deep with your crew, this is your spot.
🌲 Good vibes
🔥 Open air & bonfires
🍔 Food trucks & vendors
🎶 Live music + jams
🍻 Drinks flowing (Ladies Night = 50% off!)
⚡ MAY 21st SPECIAL ⚡
We’re turning it up a notch…
🎤 Featuring Party Marty’s
🎸 The Famous Jackass Open Jam
Calling musicians from all over the Midwest — bring your instruments, plug in, and take over the Jackass Saloon stage. This is your chance to jump in, collaborate, and make some magic.
🕕 Musicians Sign-up at 6PM
🎶 Music 7:01pm.
🕒 Event runs 3PM–11PM
🚫 No cover
Listening Party
May 22, 2026 | 7:00 pm - 10:00 pm🎶 LISTENING PARTY • LIVE AT JENNINGS HOLLER 🎶
Milwaukee’s own Listening Party is rolling in Friday, May 22nd from 7PM–10PM bringing that rich Midwestern Americana sound to the Jackass Saloon Stage 🤠
🔥 FREE • NO COVER • JUST SHOW UP
—Jackass Saloon Stage—
📍 W379 S9674, County Rd S, Eagle, WI
✨ Free music. Good people. Unforgettable vibes.
Cold drinks, real tunes, and a night in the Holler you won’t forget.
Dead Bike Night - Heads All Empty
June 4, 2026 | 3:00 pm - 11:00 pm.🔥 BIKE NIGHT AT JENNINGS HOLLER 🔥
Rev it up and ride out to the heart of the Kettle Moraine State Forest for a special edition of Bike Night…
⚡ DEAD BIKE NIGHT – WAVE THAT FLAG FEST SHOWCASE ⚡ 🏍️🌹⚡
Every Thursday we ride—but this one hits different. We’re bringing the spirit of the lot, the jams, and the magic of the Dead straight to the Holler. Calling all clubs, nomads, deadheads, and motorcycle enthusiasts to roll in and ride together.
🌲 Good vibes
🔥 Bonfires & open air hangs
🍔 Food trucks & vendors
🍻 Drinks flowing (Ladies Night = 50% off!)
🎶 Extended jam energy all night
🌹 SPECIAL FEATURE 🌹
🎸 Featuring Heads All Empty
⚡ A tribute to the very best of Grateful Dead
Get ready for a night of psychedelic jams, timeless grooves, and that unmistakable Dead energy under the stars. Whether you’re chasing the sound or just finding it for the first time—this is where you want to be. A pre- Showcase for our Wave That Flag Fest Jul 2-4
Music Festivals
Feed Your Head Fest
Wise Fest
Arts & Craft Fairs
Bluegrass German Christmas Market
Christmas at the Ranch
Mothers Day Weekend
Concerts
Bike Nights
Sundays
Live Music at the Saloon
Pop Up Shows






