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This adventure intertwines a road trip, a vintage sports car weekend, my 16-year- old grandson, Porsches of course, and more.

The starting point was Christmas Day, 2021. My gift to grandson Bentley was an allexpenses paid road trip to Elkhart Lake, Wisconsin, the site of the Road America Road course, and the annual Weather Tech International Vintage Challenge with Brian Redman.

Road America is one of the premiere road racing courses in North America, very well liked by drivers and spectators. Nestled in a wooded, park like setting, the track offers a variety of challenges for drivers. High speed Ss, a sweeping carousel, and major changes of elevation are just some of the obstacles. Spectators can immerse themselves into the action at several locations around the track, as they are only a few feet away from the rocketing race cars.

Racing in Elkhart began in 1950, right in the center of town. Using a combination of city streets and adjoining country roads lined with exposed trees and occasional “protective” hay bales, the course became quite popular. But in 1952, due to several racing mishaps, the temporary circuit was shuttered and a dedicated race track was drawn up. Local racing began at the new facility, today’s track, in 1955.

Moving forward: On a sunlit July morning, Bentley and I departed Blue Springs, Missouri, for Elkhart Lake, some 500 miles northeast. However, Bentley had just recently come intopossession of a 2011 Nissan 370Z. Filled with pride in his first car, Bentley insisted on driving.

Off we motored. The Z, although comfortable on lumpy midwestern highways, lacked my Cayman’s punch, and luggage space. But guys only need a change of underwear and a toothbrush. We were good to go.

Our home away from home was Sheboygan Falls, Wisconsin, just 20 minutes southeast of Road America. Thursday morning, after taking in the free, not so tasty breakfast at the hotel, we drove to the track.

Today was test day on the 4-mile course for the 400 plus cars entered in the weekend’s races. In 11 different groups, with as many as 5 different classes within each group, were a mixture of brands, models and years. As an example, there were 1960 Porsches and BMWs, combined with 1970 Datsuns and Lotuses. The earth shaking CanAm monsters, growling NASCARs, and ear-shattering Formula 1 screamers had their own classes.

Icing on the cake was a gathering of 29 Dan Gurney built Eagles. Perhaps the most famous in this nest of cars was Dan’s winning Formula 1 car. This car made him the only American builder and driver to win a F1 race. Normally this historic car is on display at the Revs Institute and Museum in Naples, Florida. Twice I have visited the Revs, and each time this car was out on loan. Finally, my boyhood dream racing car quest was satisfied by being able to see and touch it here at Road America.

Friday, I surprised Bentley with the opportunity for him to drive his car on track. For me his ear to ear grin was the best part of the trip. We and others followed a pace car around the famous venue for several low speed (65 mph) laps, but it seemed fast enough for first timer Bentley.

That evening events moved to downtown Elkhart, just five minutes north of the track. At 6:00 pm, a large contingent of the attending race cars roared into town, stopping at the end of Main Street. This gave bystanders the opportunity to snap up close photos of the cars and engage in conversations with drivers and owners.

Saturday, things on track got serious, as qualifying began. The sound of 1950’s Porsche Speedsters mixed with screeching 90’s Shadows and others was automotive music to my ears.

Saturday evening, we returned to the streets of Elkhart for a parade of exotics. Never have I seen so many different models of Ferraris in one location, except perhaps Rodeo Drive. They were fender to fender, sharing the street with rare models of 911 Porsches, Lambos, Jaguars and others. Adjacent to this eye candy collection is the infamous inn/bar, the Siebkens. The walls, ceiling and floor of the bar are covered with racing memorabilia. David Hobbs, famed multi talented race driver/racing broadcaster and author, would gather here with fellow competitors after races. Tales of should have, would have, could have no doubt regaled into

the wee hours of the morning. That tradition continues today with current drivers.


Each night, post racing, Bentley and I would drive the short distance east to the town of Sheboygan, which sits on the shores of Lake Michigan. For decades families from Chicago, Milwaukee and other upper Midwestern cities have spent their summer holidays here. Young and old soak up the refreshing waters and cooler temperatures. A mixture of early 20th century inns and bed and breakfasts, along with refurbished restaurants and bars offer a quaint and relaxing environment.

Sunday, we watched the races from the comfort of the tower. The tower sits directly across from the pits and track, and next to the start/finish line. Here timing and scoring are kept. For an upcharge, fans can have the pleasure of relaxing in the public part of the tower, consume breakfast and lunch, wash it down with coffee, sodas and beer, (just me with the beer), watch closed circuit track TV, and rest feet and legs.

After four terrific days of eyeballing the on-track action and wandering through the pits, we squeezed into the Z and headed home, with great memories stored in our heads.

As with many road trips, you get to know your riding companion better. No doubt a communication gap exists between a 76-year-old and a 16-year-old. However, by the end of the trip, Bentley and I had expanded our understanding of each other and narrowed that age gap. Very rewarding.

For a car guy, photographer and grandfather, I couldn’t have asked for a better weekend. Before it’s too late, take your grandchildren, spouse or best friend on a road trip. I guarantee you, it will be one of your best experiences behind the wheel, especially a Porsche steering wheel or maybe a 370Z, that you will ever have.

Next up, a road trip to Pikes Peak with fellow Kansas City Porsche Club members. Stay tuned. See you on the road. . .in a Porsche.

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