Rockin’ at the Roof Garden

West Lake Okoboji was the backdrop on that early summer evening in June of 1957. From the second floor windows of the Roof Garden, opened wide to the refreshing lakeside breezes, came the signature baritone, gravelly voice that helped fashion ‘50s rock n’ roll, Johnny Cash. The music that would shape the conscience of a generation drifted out over the lake, settling afar in the waves, to be kept there forever. Northwest Iowa would never be the same.

There are places in everyone’s lives that resonate with bold memories, buried deep into our psyches. It’s not so much the buildings – although you may recall the curvatures of the windows or the warmth of the sheer immensity of the wooden dance floors – but the keepsakes they evoked.

In the Iowa Great Lakes, that someplace was the Roof Garden, that two-story edifice in the heart of The Park that for more than six decades hosted some of the most renowned big band and rock n’ roll groups in the history of American music. The Roof Garden lives on in the memories of fans nationwide as the place where innocence and great music rocked side by side.

No musical venue in the Midwest has prompted more flashbacks for Baby Boomers and other generations than the venerable Roof Garden in The Park on West Lake Okoboji.

Built at The Park above the lakeside retail stores by Spencer Construction, the Roof Garden opened on June 23, 1923, under the ownership of Dr. A. L. Peck, with Al Grabel’s Broadway Entertainers appearing on stage. With an estimated 400 couples cavorting on the dance floor – which had a moonlight effect caused by four spotlights thrown on revolving mirrors – patrons recalled the deck literally rising and falling with the rhythm of the dancing.

With a veranda that extended around the entire 100 by 162-foot floor, the Roof Garden was then the second largest dance hall in the country. Customers enjoyed climbing its famous stairway and promenading on the landing and walkway.

During the 30s and 40s the hottest big bands in the U.S. made regular stops at The Roof. The Big Band era was a golden time for the Roof Garden, with such marquee acts as Tommy Dorsey, Glenn Miller and Louie Armstrong performing for enthralled music lovers who danced the nights away. Our peers have cherished memories of the swing bands that graced the Roof Garden stage.

The mastermind behind the rock movement, in the 1950s, at the Roof Garden was Darlowe Oleson, who owned and operated the property during its heyday. Darlowe Oleson, Bernie Storek and silent partner Carl Thacker took ownership of it in the 50s. Known as a destination for big band and swing music during its first 30 years of operation, it was Oleson who rolled the dice and predicted prophetically that rock n’ roll was the next wave of the future. In 1955, Oleson brought the first rock act – the Crew Cuts from Toronto, Canada – to the Roof Garden. The show was a hit and for the next two decades – until his tragic passing in a plane crash in 1973 – Oleson was regarded in the industry as a master promoter, turning the Roof Garden into a most sought-after destination for big name bands. In between 1956 and 1969, Oleson owned five ballrooms in Iowa. He has been recognized as the man who first brought rock and roll music to the Midwest ballrooms. Darlowe was a businessman who kenw ballrooms could not continue on with just big bands, there had to be a way to get teens in the doors, …thus rock and roll.

Teens and adults, young and old, rocked to the sounds of some of the most enduring bands of the era: Mitch Ryder & the Detroit Wheels, The Box Tops, The Everly Brothers, The Turtles, Roy Orbison, and The Flippers, just to name a few.


No ballroom venue in the entire Midwest established more of a rock n’ roll identity than the Roof Garden. In Iowa alone, more than 200 ballrooms flourished in the ‘50s and ‘60s, even in the tiniest communities. ‘Garage bands,’ – those start-up groups of young rockers with big dreams and a love of music – sprung up in small towns across the state. Securing a gig at the Roof Garden was every band’s dream.

Sweet rock ‘n roll music spilled out of the Roof Garden windows into Okoboji nights, setting the stage for summertime memories: Flirtations and walks on the beach, the makings of vacation dreamscapes and music that shaped our souls.

Take 1968 for example. LBJ, Lyndon Baines Johnson, was in the White House. The Beatles were all the rage.  Vietnam was escalating and growing evermore contentious. Civil rights unrest divided the country. It was an uncertain time for America. The age of innocence, however – while eroding on the national stage – was still intact in special places like the Roof Garden.

In the lakes area, Mother Nature added to the strife when a tornado touched down at the south end of West Lake Okoboji on June 13, damaging personal properties and ripping the very roof off the storied Roof Garden where Baby Boomers – entering the age of enlightenment – had rocked the nights away for so many years.

Undeterred, the owners patched the Roof Garden into habitable shape – ironically sans roof – and on July 2 Sam the Sham & the Pharaohs crooned for an overflow crowd that paid a $1.50 admission fee. Music had once again rescued the consciousness of a generation.

The Roof Garden underwent several ownership and musical transformations over the decades, ending in disaster when the structure was razed on October 2, 1988 as a practice burn for local firefighters.

It’s hard to find folks who don’t have some keepsake memories of the old Roof Garden. From the big band acts of the swing era to the rock generation and on to pop and beyond, we can all hark back to summer nights at Okoboji when music was king and mementos were enshrined in the rafters of the Roof Garden.