2022 Lineup coming soon!

2021 Artist lineup


Hailing from the river town of Stevens Point, Wisconsin, Horseshoes & HandGrenades plays something like progressive high-energy Old-Time folk music. With strong roots in old-time and bluegrass, the band has formed its own unique style born from the diverse musical backgrounds and interests of the five friends who make up the band. All born and raised in the great state of Wisconsin, HHG began playing music and their earliest shows in the spring of 2009. Being mostly inspired by rivers, valleys, good friends, and good drink, this five piece is as sturdy as any Midwest riverbed and will make your toes tap from sundown to sunrise


In mythology, the hawk is often associated with intuition, healing, spiritual awareness and unification. They seem to appear when you need them most, evoking a feeling of clarity, focus, or maybe courage. The word supergroup gets overused to describe side musical projects, but it’s apt and well-earned when it comes to The High Hawks. With nearly 150 years of collective touring and playing between them, Vince Herman (Leftover Salmon), Tim Carbone (Railroad Earth, Blue Sparks From Hell), Chad Staehly (Hard Working Americans), Adam Greuel (Horseshoes & Hand Grenades), Brian Adams (DeadPhish Orchestra) and Will Trask (Great American Taxi) have maintained a generation-spanning presence at the forefront of the roots music scene for over two decades

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Jon Stickley Trio is a genre-defying and cinematic instrumental trio, who’s deep grooves, innovative flatpicking, and sultry-spacy violin moves the listener’s head, heart, and feet. “It’s not your father’s acoustic-guitar music—although Stickley’s pop showed him his first chords when he was 12 years old. Instead, Stickley’s Martin churns out a mixture of bluegrass, Chuck Berry, metal, prog, grunge, and assorted other genres—all thoroughly integrated into a personal style,” writes Guitar Player Magazine. With inspiration ranging from from Green Day to Duran Duran to Tony Rice to Nirvana, Grateful Dead, David Grisman and beyond, the Trio is making waves with their unique sound. 


From Cincinatti, Ohio, The Tillers have been thumping their own distinctive sound of string band style folk music for a decade, riding it all over the country and across the sea. Four studio albums and one live record have won them praise as modern folk storytellers of the national soundscape.


"Like no other group I’ve ever heard, the Tillers are able to break your heart with an intangible, timeless pain.  Combined they harmonize like the Celestial Monochorde of old, awakening once again the ancient muses to strum the heartstrings of man..."

- Col. JD Wilkes


Your host band, Sloppy Joe has been playing their own style of bluegrass inspired neo old-time  music,  lovingly penned as Slopgrass, since 1998. A talented and musically diverse group of individuals, the band swaps instruments right and left throughout their high energy performances,  keeping the audience dancing and on their toes.  Celebrating their 20th year together, the band continues their mission to preserve Slopgrass music for generations to come, and welcomes you to join the Jackpine Family on Labor day Weekend!


From Madison, Wisconsin, Armchair Boogie takes progressive bluegrass to new heights by genre-bending in the funkiest of fashions. Their high-energy take on the Jamgrass genre fuses intricate arrangements of acoustic guitar and banjo with the funky backbeats of electric bass and drums. This dynamic sound covers everything from lightning-fast bluegrass to firey funk to honky-tonk. Since the release of their debut album in spring 2018, Armchair Boogie has quickly risen to become a nationally touring band, entertaining audiences across the midwest to the Rocky Mountains and beyond.    


The Yankee Coalition

The Jackpine is your only chance to see the boys from The Yankee Coalition play as they once did back in the days of The Great Northern Bluegrass Festival (Mole Lake, WI).  Tuck Pence is a well renowned musician in his own right, but when backed by Danny Lincoln -banjo wizard and pedal steel extraordinaire, Joe Cronick -alias "mandolin man", the uncle of Bluegrass-  G.T. "Doghouse" Hauser, and Donny Lincoln, it is a show not to be missed!


​Singer/Songwriter/Multi-Instrumentalist Joseph Huber was a founding member of the .357 String Band--a group that, despite its abrupt break-up, still continues to gain popularity and is known as one of the most influential groups in the recent insurgent underground country and bluegrass movement. Having moved from .357, Huber has honed his songwriting abilities immensely and now continues moving onward and upward captivating folks with his sincere and well-crafted songs under his own name and with his backing band. Whether it's irresistible, fiddle-driven, dancing tunes or honest, heart-wrenching "songwriter" songs, Huber spans the spectrum of 'Roots' music while preferring not to stay within the boundaries of any strict genre classification.


Wisconsin’s hardest working musician, Singer-songwriter, Tuck Pence  has been in the music business for over 30 years, and has performed every Jackpine to date. With a repertoire of over 2,000 songs, 4 albums, and years of being on the road under his belt, Tuck is truly an American Relic.  An astounding performer, and true friend, he is the finest example we know of what great musicianship really means.


Dig Deep is a four-piece string band based out of Wisconsin that has in a very short time become a truly unique voice and a cornerstone of the thriving Midwest roots community. Through tireless full-time touring throughout the upper Midwest and across the country, the release of an acclaimed debut album, numerous high-profile festival and theater appearances,  Dig Deep has earned love from fans, respect from musicians, and rapport with venues and events with their well-honed, hard-edged sound and their boisterous, dynamic performances.


 Art Stevenson has foraged up a few familiar faces to join him at this year's Jamboree. 

Art IS Bluegrass in Wisconsin, and has been performing for over four decades in the midwest and beyond. Joining him and "keeping the drive alive on the old five" is banjo extraordinaire Dale Reichert. The combination of Art's truly lonesome vocals, fire breathing harmonica,  and Dale's driving banjo, along with The Foragers own Stef Lee holding it down on the low end and Bobby Burns' spitfire mandolin playing is sure to be a set to remember! 


Insomniac Gypsy is an original, bluegrass-infused, high-energy string band, infusing bluegrass with jazz, funk, and rock to come up with a completely different sound all their own. Denny Vanesky’s song writing takes center stage as he conjures up songs about his colorful life and the people and experiences he has met with along the way. His raspy and intense vocals are that of a backwoods storyteller,  and his playing-with-fire, hot picking guitar style is as flavorful as a Kentucky barbecue. Rounding out the band are the multi-talented Gypsies, whose playing is always a blend of technical basting and improvised seasoning. Good tasting, dance-around-the-fire nourishment!


Scott Kirby has been cultivating his own brand of Americana "blue country-folk grass" for over a decade. This particular blend of styles, allows Kirby to connect with an array of audiences. Kirby's musical inspirations are like patches he prominently displays- from the straightforward sensibilities of Johnny Cash, Willie Nelson & B.B. King- to the musical explorations of the Grateful Dead, The Allman Brothers, and Bob Dylan. Kirby's got a soulful voice that delivers each story with sparkling authenticity and is truly at home whenever he's playing his music-   


Much like the mythical Hodag, the Old Pine Road Band has emerged from the woods of northern Wisconsin to mystify, captivate and entertain its many fine inhabitants. for nearly a decade, David Walters and the old pine road boys have been combining a crowd-pleasing blend of soulful funk-grass with a taste of twang and jam-band experimentation that's sure to leave you entertained


We are a group of people that gather together in an array of numbers these days. A Key Three will get you a Tuesday. A Core Four is that and more. A Five Alive and you might find Wednesday. It is a pleasure to gather and a grace to play. Walking down an old familiar path or discovering a new one, it is the music, it is the muse, it is such good stuff for the soul. And then there's the times we come to your town and do it with you - talk about all that and more! Dewgrass keeps keeping on and we wouldn't have it any other way

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Deep voluptuous tones of the upright bass that  intermingle around introspective lyrics is what creates the caws of The Low Crows.

Featuring the incredibly talented Samual Odin on Upright Bass (Horseshoes & Hand Grenades) and Singer/Songwriter Lynn Salzman on Baritone Ukulele. (Ukelyptus)




Masterful storytelling and incredible musicianship combine for a rare treat of a performance.

Playing tunes from their debut album, Love From The Oven, Denny and Lyndsay will make you want to light the oven, turn up the heat, shake it to that old time beat. 

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The Hand-Picked Bluegrass Band is a high energy acoustic band playing everything from the traditional “high lonesome sound” of Bill Monroe’s Bluegrass Boys to the exciting sound of today’s progressive bluegrass groups – as well as their own original music.  Featuring a high caliber lineup, fronted by the husband and wife team of Joe and Sue Cronick, they deliver a show of stellar picking and powerful vocal arrangements. You can be sure that each and every performance will be a special one!

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Star Valley Ramblers

Poppin' off some reels of fiery old time tunes and feisty trouts are some of this band's choice activities.  The fiddle, clawhammer banjo, guitar and bass blend into an extremely dance able and enjoyable combination, sure to make even the most stoic of Jackpiners tap a toe. 

The trio of songwriters, known as Ukelyptus, fuse sweet vocal harmonies with the sounds of the baritone ukulele, mandolin, and bass fiddle to create a truly captivating and original sound. Playing together since 2014, Ukelyptus released their first album "Open A Doorway" in August of 2015....Imagine mermaids...

Kevin John Troestler (age 27) is a blues/country artist raised in Sauk City, WI. Bluegrass, Country, and Blues. He is currently living in Appleton, WI performing all over solo acoustic to a full band. His debut E.P. “Devil’s Grip” is OUT NOW

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The New Hope Hay Balers

Toe tappin gospel tunes sure to kick off Sunday morning with some spirit!


***Lineup subject to change***