Rollin’ Oldies Car Show Brings Classic Cars and Their Stories to Oskaloosa
Chris Parrish’s restored 1950 Cadillac Series 62 convertible sits on display during the 38th annual Rollin’ Oldies Car Show on July 18, 2026, in downtown Oskaloosa.
OSKALOOSA, Iowa – On Saturday, July 18, classic cars, trucks, and other collector vehicles lined the streets around the downtown square for the 38th annual Rollin’ Oldies Car Show.
The Rollin’ Oldies Car Club hosted the event, bringing together vehicle owners and visitors for a day filled with cars, prizes, and activities. According to the City of Oskaloosa’s event listing, the show typically attracts about 200 vehicles to downtown.
Cars were parked along the north, south, and east sides of the square. The show also stretched into part of North First Street and the 200 block of High Avenue East.
Activities included a downtown poker walk, voting by vehicle owners, cash drawings, prizes, and awards. The club handed out free root beer during the show.
After the event, the Rollin’ Oldies Car Club announced that a 1961 Chevrolet Biscayne won the judges’ Best in Show award.
One of the owners at this year’s show was Chris Parrish, who brought his 1950 Cadillac Series 62 convertible.
Parrish told Oskaloosa News he had hoped to attend the show in past years, but rainy weather kept him from bringing the Cadillac since he prefers not to take the convertible out in the rain.
Parrish knows several people in the Oskaloosa car community. Thanks to good weather this year, he was able to bring the Cadillac to the downtown square.
The Cadillac is one of fewer than 7,000 Series 62 convertibles made in 1950. Parrish’s car was built for sale outside the United States, so its speedometer goes up to 165 kilometers per hour instead of showing miles per hour.
According to information that came with the car, it spent some time in Argentina. Parrish said he heard that when the Cadillac came back to the United States, every body panel was a different color. The car has since been restored and now has a matching finish.
Parrish often goes to car shows and sometimes attends one or two in a weekend. He said the Oskaloosa show gave him a chance to see cars he hadn’t seen at other events.
For Parrish, car shows are also a way to meet people. Owners get to share the history of their vehicles, and visitors often talk about cars they used to own or ride in.
Parrish said people often come up to him and mention they once had a Cadillac like his 1950 convertible.
The annual Rollin’ Oldies show still gives residents and visitors a chance to see antique, restored, and customized vehicles while enjoying time in downtown Oskaloosa.
