🌞🎶 Spend a summer evening on the banks of the Mississippi with great music, dancing, local vendors, food, and plenty of Grateful Dead classics. Winona Is Dead brings together some of Winona's favorite musicians for an unforgettable celebration of the Grateful Dead. Expect a unique setlist packed with improvisation, deep cuts, and the timeless songs […]

🎶 Making their Trempealeau Hotel debut! The Cedar County Cobras bring the sound of old-school American Roots and Blues to the riverside, armed with an upright bass, foot drum, and a handful of guitars. Their gritty, stripped-down style feels like it drifted out of a juke joint at the end of a dusty Iowa gravel […]

Get ready for an unforgettable night of blues as Howard "Guitar" Luedtke and Dave Rogers reunite for their annual birthday celebration. When these longtime friends share the stage, it's more than a concert. It's a gathering of musicians, friends, and blues fans, with a few surprise guests likely to join the fun. The evening opens […]

Sophie Coyote is a singer-songwriter from Waddams Grove, Illinois, a quiet Midwestern pocket where old farmhouses sit back from long stretches of field and sky. Growing up in that wide-open landscape, she was surrounded by a mix of sounds that ran from classic rock and roll to honky-tonk country, with a healthy streak of blues […]

The People Brothers Band brings an unforgettable blend of soul, funk, and roots music with a live show full of energy, heart, and connection. Joined by The Getaway, this is a night built for dancing, good vibes, and letting the music move you. Bring your best dance moves and most colorful threads. Come celebrate love, […]

The Mascot Theory Duo of singer/songwriter/acoustic guitarist Erik Kjelland and electric guitarist extraordinaire Cory Swadley perform unique, stripped-down versions of the full band’s catalogue of original folk rock music. Their music is known for emotionally honest songwriting, soaring harmonies, and a sound that moves fluidly between introspective folk-rock and full-throttle, heartland anthems.

The Flyin’ A’s are a husband-and-wife Americana duo—Hilary Claire Adamson and Stuart Adamson—now based in Austin, Texas. While their home base is southern, their touring life has a strong Upper Midwest thread, with regular stops through Wisconsin, Minnesota, Colorado, and the broader folk and Americana festival circuit. Hilary’s roots trace back to La Crosse, Wisconsin, […]

The La Crosse Confluence is a high energy cover band of talented high school musicians. The band plays an incredible variety of music from Aretha Franklin to Adele, from Charlie Daniels Band to Dave Matthews Band and everything in between (and beyond). Launched in 2023, The La Crosse Confluence continues to inspire and impress audiences […]

Minneapolis singer-songwriter Jimmy Peterson returns, bringing a mix of original songs and covers that encapsulate his take on American music. His music gives a super chill vibe that goes well with a relaxed night on the river.

Poetic. Electric. Americana. Lone Goat Rodeo, led by songwriter Tim Eddy, rides into the Trempealeau Hotel with Sean Truskowski on drums and Jessie McDonald on violin. Inspired by the likes of Willie Nelson, Tom Waits, Lucinda Williams, and Guy Clark, their songs blend rich storytelling, honest emotion, and rootsy musicianship into a sound all their […]

Nicolle Roen and Sally Reimer make up the Balkan Blue Duo. Join them for an evening of captivating melodies, rich traditions, and rhythmic surprises from across the Balkans and beyond. Featuring music from Bulgaria, Macedonia, Andalusia, Turkey, Albania, Hungary, and the Roma people, Balkan Blue blends folk traditions with modern influences, weaving timeless stories through […]

🎷🎥 LIVE Recording Session with the Winona Jazz Collective! 🎶 Be part of the audience as we capture two live audio/video sets featuring original compositions and fresh takes on music by The Beatles, Sting, Grover Washington Jr., John Scofield, Pat Metheny, and more. This FREE event marks the first time all nine members of the […]

Kick off summer with Them Coulee Boys and Clay Fulton & the Lost 40! Them Coulee Boys return to the Hotel with songs from their acclaimed new album No Fun in the Chrysalis, recorded in Eau Claire with Grammy winner Brian Joseph. Expect two nights of high-energy Americana, fan favorites, and no repeat sets. Plus, […]

From mountaintop farms and horse barns to sold-out stages and recording studios, Pat Sheridan has had quite the journey as a burgeoning young musician.

Acclaimed singer-songwriter Pieta Brown has spent more than two decades crafting deeply personal folk and Americana music marked by luminous songwriting and a haunting, unmistakable voice. A favorite of critics and fellow musicians alike, Brown has toured worldwide with artists including John Prine, Ani DiFranco, and Mavis Staples, while earning praise from NPR Music, Billboard, […]

The Substitutes (formerly The Subs) are a group of longtime substitute teachers and early members of the Organic Music Cooperative who turned shared downtime into a shared downbeat. Featuring Gregg Hilker on ukulele, banjo, guitar, and assorted stringed wonders; Kris Risch on guitar; Lisa Risch on keys and tambourine; and Phil Gilbert holding down all […]

Marques Morel is a Midwestern troubadour with a dust-on-the-boots voice and stories to match. Raised in Illinois corn country, he’s played everywhere from street corners to festival stages, sharing bills with the likes of Charlie Parr and Joe Pug. His latest album, Tales and Tellings, earned national praise for its sharp writing and roadworn heart. […]

It’s been nearly a year since we last hosted The Brothers. Time to fix that. Expect something surreal and seriously good. Brothers Burn Mountain—Jesse and Ryan Dermody—built a studio deep in the Minnesota woods, chasing the sounds of wind, rain, and nightfall. The guitar-drum duo has played 2,000+ shows over 25 years. Their 11th album, […]

Todd Saner and Tom Gibbons are back—and they're bringing fresh tunes and big energy! With over 20 years of playing together in the La Crosse area, this dynamic duo covers a wide range of genres, adding their own twist to favorites, old and new. Between them, they juggle acoustic and electric guitars, mandolin, harmonica, and […]

Wes Urbaniak crafts songs that feel lived-in—honest, bold, and just the right kind of strange. A storyteller at heart, he turns life’s rough edges into something resonant and real. Even the instruments carry the tale, built from reclaimed redwood from Red Rocks Amphitheatre—Urbaniak himself the hands behind them. It’s music with a pulse, a past, […]

Hudson Valley’s own rising force Dylan Doyle is making noise far beyond his home turf, lighting up stages across the U.S. and overseas. His sound rides the line between roots rock grit and jam-funk groove, with flashes of Woodstock spirit and a deep dip into Southern soul. It’s a distinctly American blend. A natural storyteller […]

These sultry sirens weave three-part harmonies with an ease that feels almost otherworldly—often described as nothing short of magical, like flowers that only dare to bloom after dark. Their setlist glides across decades, from the 1950s to today, touching on rock, country, and pop with equal finesse. Join us in giving them a warm welcome […]

Kit Mayer & The Pack bring their signature energy and musicianship to the Winona Hotel for a special performance. The show features original songs by Kit Mayer alongside a thoughtful mix of favorites from artists who inspire the group. Known for their seamless blend of electric and acoustic styles, this performance offers an intimate twist—an […]

Mike, Nancy, and Jessie will be playing your favorite Blink songs along with fresh tracks from their upcoming album. Enjoy a special acoustic trio version of Mr. Blink featuring Jessie McDonald, Mike Caucutt, and Nancy Caucutt. The show will include beloved hits, new material, and the fan-favorite “Wisconsin Set.” You’ll hear songs inspired by Madeline […]

Join us for an afternoon of classic country and Americana with Fayme Rochelle & The Waxwings, a gentle ushering-in of spring. 🌱🎶 Blending heartfelt songwriting with warm, layered harmonies, the group crafts a sound rooted in Americana and country-rock, with a subtle trace of vintage soul. Their songs carry stories that unfold with ease, shaped […]