More than 1,500 automobiles are expected to be on display at the Kenosha Classic Cruise-In Saturday in downtown Kenosha.

Car enthusiasts to rev up downtown Saturday

Kenosha Classic Cruise-In expected to attract over 1,500 automobiles


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Behind every classic car there’s a story, just like Kenosha resident Ron Bissland’s 1956 Model Roadster 1500.

The award-winning, glacier-blue beauty is one of over 1,500 automobiles expected to be on display at the Kenosha Classic Cruise-In from 9 a.m. to 4 p.m. Saturday (Sept. 4) throughout the streets of downtown Kenosha.

The car show, which was cancelled in 2020 due to the pandemic, is free for owners and spectators and open to all makes and models. It is one of the most well-attended local events of the year, typically attracting over 10,000 people.

“I’ve been getting calls from all over the country,” said Tony Pontillo, the event organizer and member of the local car club Kenosha Classic Street Machine. “I’m scared to say how big it could be.”

Car owners interested in displaying their vehicles can form a line at 56th Street and Seventh Avenue. Gates open at 7 a.m. Saturday. 

Two years ago, there were over 100 cars lined up at 5:30 a.m., according to Pontillo.

“The police told us we had to open up because the cars were all the way to Sheridan Road,” Pontillo said.

Spectators can expect a variety of Kenosha’s own vintage muscle cars including AMXs and Javelins, plenty of Chevrolet Camaros and Corvettes, Ford Mustangs and at least a couple crowd-pleasing Plymouth ‘Cudas.

The 2019 event featured several gems including a pair of rear-engine dragsters, a Cobra kit replica and Bissland’s immaculate MGA roadster.

The roadster was purchased by Bissland’s uncle Donald Bissland, a U.S. Air Force fighter pilot who crashed his F-84 Thunderjet into the English Channel and died 18 days after buying the vehicle. 

“This car show is the best day of the year for downtown merchants.”

– Tony Pontillo, event organizer

The car remained in the family, where it was passed on to Bissland’s father, Alexander Bissland, and later his mother, Barbara Bissland. It sat in her New Jersey garage until 2010 when Ron transported the vehicle to Kenosha and spent seven years restoring it.

Purchased new for $1,785 on March 27, 1956, the roadster is worth over six figures today.

Bissland, 62, said his mom visited Kenosha two years ago for his 60th birthday.

“I took her for a ride in the car and she started to cry,” Ron Bissland said. “She said the last time she was in the car was with my dad in 1968.”

Every piece of the car was restored or replaced with original equipment. The interior leather and carpeting were ordered from England.

The roadster took first place in its first-ever car show in 2019 and won a pair of first-place awards in 2021, including ‘Best in Show” at the MG International car show Atlantic City, N.J. in June.

Bissland said he takes frequent requests to purchase the vehicle.

“I’ve been offered a lot of money,” Bissland said. “I won’t sell it. It will go to my son and then his son.”

The Kenosha Classic Cruise-In was created in 2004 and featured approximately 80 cars.

This year’s event includes a General Motors product trailer, positioned outside the Jockey Factory Store at 5500 Sixth Ave.

“General Motors asked me a couple years ago if I was interested in having them,” Pontillo said. “I figured they wouldn’t come to little old Kenosha. This is the first time they’ll be here. I’ve never seen the trailer, but I heard it’s fantastic.”

Live entertainment will be provided by “All the King’s Men” and its popular Elvis impersonator.

Attendees are encouraged to bring non-perishable food items to place in several bins to be donated to the Salvation Army.

“This car show is the best day of the year for downtown merchants,” Pontillo said. “A lot of us grew up downtown. We used to scoop the loop. We want to make sure downtown makes it. It’s in our blood.”

The Kenosha Classic Cruise-In was created in 2004.