
Live Music, Good Company, and Kettle Moraine Charm.

Sauna Synergy
April 10, 2026 @ 12:00 pm - April 12, 2026 @ 10:00 pmBluegrass Stew Sunday
April 12, 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 April 12 from 2–5 PM at the Jennings Holler – Jackass Saloon for Bluegrass Stew Sunday, featuring the soulful sounds of Luke Cerny & friends.
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
Come hungry. Come ready. Come Holler.
If you want, I can also make a shorter version for Instagram captions or a flyer-style graphic version.
Huffman Wahlen Duo
April 17, 2026 | 7:00 pm - 10:00 pm🎶 Live at Jennings Holler – Huffman-Whalen Duo 🎶
Blending rock & roll classics, country favorites, and reggae rhythms, this duo delivers a laid-back yet lively sound that’s perfect for kicking back with a drink or getting up and dancing.
📅 April 17th
⏰ 7PM – 10PM
📍 Jackass Saloon Stage – Jennings Holler
W379 S9674, County Rd S, Eagle, WI
Cold drinks. Good company. Real music.
Come catch a vibe at the Holler.
Bluegrass Stew Sunday - Joe Wais & Friends
April 19, 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 April 19th from 2–5 PM at the Jennings Holler – Jackass Saloon for Bluegrass Stew Sunday, featuring the soulful STRING sounds of JOE WAIS (FROM THE MILLBILIES) & FRIENDS
Expect rich harmonies, driving acoustic rhythms, and that down-home bluegrass energy that hits just right.
🍲 Food by Baked & Loaded
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
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 - 11:58 pmBluegrass 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 pmCraft Cocktail Workshop with Robyn
May 2, 2026 | 3:00 pm - 5:00 pmWise 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 🍻
Mother's Day Extravaganza!
May 10, 2026 | 11:00 am - 5:00 pmBring a Mom out to the Holler for a great mother’s day with food, music and a plant class!
Byrants on the Round presents:
All you can eat Brunch buffet & omelet station! Served 11am – 3pm
$40 adults
$15 kids 12 & under
Hanging Basket workshop with Geske’s Gardens starts at 12pm $40
Live Bluegrass Music starting at 2pm
Hanging Baskets (Mother's Day)
May 10, 2026 | 12:00 pm - 2:00 pmBike 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.
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
BEST OF ALL FESTIVALL
May 28, 2026 @ 8:00 am - May 31, 2026 @ 1:00 amLets welcome our big beautiful massive lineup
For Best Of All FestivALL
Music – Art – Camping
May 28-30th
Jason Kane & The Jive
Saltydog
Lunar Ticks
Wise Jennings
Party Marty & The Dirtbags
Matt Waters & The Recipe
Newski
Jon Sullivan Band
TWINE
BAMM
Alabaster
Honey Fingers
Whiskey and the Devil
Spare Change Trio
Gin Mill Hallow
Juiceneck
Tha Mid City Kid
Da Goff Rockers
Trash Panda
Matt Pless
Derek Ramnarace
Pete Jive
Whitney Rose
Rhetoric Vendetta
Winterkill
Black Moon Lilith
The Cult Of Nasty
Bellends
5 o’clock Charlie
The Malones
McClusky & Gunn
Gene Gruber
Jon Rouse
Aaron Williams & Jules
Jason Petit
Just Dusty
All Happening right here at Jennings Holler
W379 S9674, County Rd S, Eagle, WI 53119
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
Porch Planter Class
June 18, 2026 | 4:00 pm - 6:00 pmMEDICINE OF THE SUMMER SOULSTICE
June 19, 2026 @ 5:00 pm - June 21, 2026 @ 2:00 pmMEDICINE OF SUMMER SOULSTICE
– CEREMONIAL RETREAT & CAMPING EXPERIENCE.
June 19th-21st
Camping & ceremonial retreat.
🌞 Sacred Medicine of the Soulstice
A 3-Day Immersive Retreat of Earth, Spirit & Ancestral Connection.
Step into a powerful container of healing, remembrance, and reconnection during the height of the summer solstice. Sacred Medicine of the Soulstice is a 3-day, land-based retreat devoted to the sacred traditions of plant medicines from the Amazon, Northern Europe, and North America.
This is an invitation to slow down, root deeply into the Earth, and open yourself to the wisdom of ancient practices carried through time.
Through ceremony, intentional nourishment, and community connection, we gather in a sacred space to align with the rhythms of nature and the cosmos.
🔥 What to Expect:
Sacred plant medicine ceremonies (Hapé, Sananga, Cacao)
Earth-based practices and solstice rituals
Community meals and intentional nourishment
Fire, water, and sauna experiences
Creative expression and integration circles
Deep connection to self, others, and spirit.
🌲 Retreat Guidelines:
3-day commitment required (no partial attendance) Food is provided but not for specific dietary restrictions.
Vegetarian options available.
Eat at your own risk.
[made by community attending]
Tent camping only – fully immerse in the land
Bring personal snacks and camping essentials(tent, sleeping bag , pillows,)
no Alcohol/ illegal substances
Come with an open heart and respect for sacred traditions given.
🌿 Itinerary
Friday | June 19 – Arrival & Intention
5:00 PM – Arrival & Check-In
5:30 PM – Camp Setup
6:00 PM – Community Introduction & Opening Integration Circle
7:00 PM – Fireside Meal & Sacred Solstice Intention Setting
8:00 PM – Earth Sauna Lodge Experience
Saturday – Ceremony & Connection
9:00 AM – Community Yoga
10:00 AM – Light Fireside Meal (please bring snacks)
12:00 PM – Hapé & Sananga Ceremony
3:00 PM – Cacao Ceremony
6:00 PM – Community Food Preparation & Sacred Feast
8:00 PM – Fire & Water Solstice Ceremony
Sunday – Integration & Closing
9:00 AM – Self Sun-Soul Portrait Art 🎨
11:30 AM – Final Integration Circle
2:00 PM – Departure & Closing
🌕 This is more than an event — it is a ceremony of remembrance.
A return to the rhythms of the Earth.
A reconnection to the medicine within.
Registration in advance, email will be sent out for preparation and guidance.
text [414]467-9708 for information.
no refunds permitted. Rain or shine event will not be rescheduled.
Wave That Flag Festival
July 2, 2026 @ 8:00 am - July 4, 2026 @ 11:00 pmWAVE THAT FLAG ⚡🌹
A Grateful Weekend of Music, Camping, and Community!
📅 July 2 – 4, 2026 📍 Jennings Holler Eagle, Wisconsin
Join us this July 2nd through the 4th for Wave That Flag, a three day celebration of the timeless music, spirit, and culture of the Grateful Dead. This is more than a festival; it is a gathering of heads, hearts, and souls coming together under the stars to honor the songs that changed generations. 🌌🎶 We are bringing together the best Grateful Dead artists from all across the Midwest, delivering everything from faithful recreations to deep exploratory jams inspired by the Dead’s legendary catalog. Expect long grooves, cosmic solos, and that unmistakable moment when the music takes over and the crowd becomes one 💀🌹
🏕️ Primitive camping is included with your ticket, giving you the full festival experience. RV camping available at an additional fee. Pitch a tent, sleep beneath the stars, and wake up to music floating through the trees. No hookups, no frills, just pure connection to the land, the people, and the sound 🌲✨
Beyond the stage enjoy a vibrant village filled with vendors and artisans featuring handmade goods, colorful creations, and plenty of Dead inspired magic 🎨🌀 Wander, dance, explore, and reconnect all weekend long.
Music Lineup 👇 👇👇👇👇👇👇
Mr. Blotto
Joe Marcinek Band
J. Kroe’s Very Garcia
Mission
Another One
Heads All Empty
Deadelijk
Bodhicitta
Sean McKee Band
Mike & Friends
Jeremiah Jams Band
Boney Fingers
Mikii and the Fungii’s
Live music all weekend 🎨 Vendors & art 🏕️ Primitive camping included. RV Camping available for an additional fee 🌈 Community, family, and Deadhead vibes 📍
Mums Workshop
August 27, 2026 | 4:00 pm - 6:00 pmGourd Birdhouse Class
September 3, 2026 | 4:00 pm - 6:00 pmFarmLands 2026
October 9, 2026 @ 12:00 pm - October 11, 2026 @ 5:00 pmCrack those barn doors open, and let the cattle run free!!!! Farmlands fam we present to you, The Official 2026 Line-up.
We are ECSTATIC to announce our biggest year to date, featuring SMOAKLAND, HEXXA, LUMBERJVCK, NOTIXX & a bunch more talented artists from all over the U.S.
We cant wait to have every single one of you back Bobbing to some Farm Fresh Beats!
🐄🐓🦙🐑🐏🐖🫏🐎
– CAMPING IS BACK
– 3 SIGNATURE STAGES
– BONFIRE SILENT DISCO
– SECRET STAGE w/ SECRET SETS
– IMMERSIVE ART & FIRE SPINNERS
– FOOD AND VENDORS
– EXCLUSIVE MERCH & SOOOOOO MUCH MORE!!!
TICKETS ON SALE NOW!!!!
plant class (tbd)
November 14, 2026 | 1:00 pm - 3:00 pm
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.



