How well do you know the history of racing in The Region? The Midwest? America? What if I told you, that the history of auto racing in the US can trace its lineage to a single race – held in Chicago.
Before we get into the rich, storied history of racing in America as a whole, let’s head back to the birthplace of racing in America – right here in The Region. Here are the stories of 5 races that took place in The Region (and very close by) that you’ve probably never heard before.


1. The Chicago Times-Herald Race (1895)


Many people don’t know that the first race ever held in the United States was held in Chicago – The Chicago Times-Herald Race of 1895, held on Thanksgiving Day. The automobile had only just made it to America two years prior, and the Chicago Times-Herald wasted no time organizing the race – both as a form of promotion for the budding American auto industry, and to boost sales of the paper itself. Prizes for race winners totaled $5,000 (worth appx. $165,000 when adjusted for inflation in 2022).


The race route ran 54 miles (87 km) from Chicago to Evanston and back – with the finish line near what is now the Chicago Museum of Science and Industry. 83 registrants were initially entered into the race, but only six arrived for the actual competition on Thanksgiving Day, November 28th, 1895. The grid was comprised of 4 automobiles and 2 motorcycles – including 3 original early automobiles built by patent inventor Karl Benz himself.
The race itself was nothing short of intense. Before the event even started, while making their way into the city, two of the drivers were stopped by police – they were forced to requisition horses to pull the cars because no legislation existed regarding driving automobiles on the city streets. The race was ultimately postponed while the Chicago Times-Herald editors convinced the city leaders to pass an ordinance to confirm the right of these vehicles to travel on city streets (a monumental moment on its own).
One Benz car driver struck a horse and had to retire, an electric entrant’s car’s batteries died due to the cold weather, and other than winner Frank Duryea’s motorized wagon, the only other car to finish the race had to be driven by Charles Brady King (a marshall) from Point 31 of the course after the original driver Oscar B. Mueller was rendered unconscious due to exposure. Intense.
The success of the race is credited as having sped up the rate of automobile development by at least five years in the United States (due to the publicity generated from the event). The commercial production of American automobiles began only a year later – and with that, American motorsport was born.
2. The Cobe Cup (1909 – 1910)


Before the golden days of the independent stock car team in the 60s & 70s, before prohibition-era bootleggers were running V8’s to and from the American countryside – there was the Cobe Cup, a countryside road course race held in Northwest Indiana in 1909 (as well as a reformatted version later at the Indianapolis Motor Speedway in 1910).
Held by the Chicago Automobile Club (and named after its President at the time, Ira Cobe), the Cobe Cup Trophy Race weekend was comprised of two competitions – the Indiana Trophy Race (for smaller cars) on Friday, June 18 and the main event Cobe Cup on Saturday, June 19.
The track, a 23.27-mile road course on (blocked off) public rural highways (as was customary at the time) stretched from a start/finish line in Crown Point, Indiana, through the Crown Point square, to Cedar Lake, then Lowell, and back to Crown Point.




















The grandstand and start/finish straight were located on Indiana Ave in Crown Point – otherwise known as 9-Mile Road. From here, racers would head north for a short 1.4-mile stretch to East Summit Street, where they made a left and an almost immediate next left onto the NE/SW diagonal stretch of Merrillville Road as it turns into Main Street – right through the Crown Point Square. The course then headed southwest towards Cedar Lake, then directly south to Lowell, before running back east to the backstretch of Indiana Ave. The combined back stretch straightaway of the course is actually equal to 8.5 miles – hence the nickname for that stretch of Indiana (that persists today) 9-Mile Road.
In preparation for use as a racecourse, pedestrian bridges were built over the road (as well as one large enough to accommodate horses), several grandstands were erected, and nine telegraph stations were in place to relay the news to the spectators.
The first to cross the finish line was Billy Bourque, however; the race was judged by shortest total racing time. Therefore, the winner of the race was actually Louis Chevrolet, with a time a few minutes shorter than Borque’s. Yes, that Louis Chevrolet.
In 1911, the race was discontinued after the Indianapolis Motor Speedway announced its own racing competition – The Indianapolis 500.
The original Cobe Cup trophy sits on display in all its glory in the Indianapolis Motor Speedway Museum, as a stately reminder of Northwest Indiana’s contribution to the birth of Indiana’s rich history of auto racing.
3. The Time The Indy 500 Borg-Warner Trophy Went Missing (1930s)


If the Indianapolis 500 holds the title for the most prestigious motorsport competition stateside, then the Borg-Warner Trophy which is awarded each year to the winner is easily one of the most famous (and infamous) pieces of Indiana racing lore in existence.
The trophy celebrates the race’s champions throughout the 500’s long and storied history, its polished silver notably featuring face sculptures of each year’s race winner to come before – a quirk which has earned it the title of “creepiest trophy” more than once in internet articles.
According to track historian Donald Davidson, one interesting anecdote about the trophy’s storied past rises above the rest. According to legend, in the 1930s a young Butler University student was given the trophy to keep safe before race day. The young man hid the trophy under his bed one night and proceeded to have a night out – however, upon his return to his fraternity house, the man found the trophy missing.
The young student began frantically searching the house from top to bottom for the trophy. It was in the frat house’s basement that the man would eventually find the Borg-Warner: surrounded by men who were drinking beer out of it (if you’ve ever wanted to know how much beer the Borg-Warner Trophy can hold, the number is somewhere around 115). Emptying the beer, the young student wondered how he would get the smell off of the trophy, and decided to take a shower – taking the trophy in with him.
All’s well that ends well, I suppose!
4. Al Unser and Team Penske Win Indy 500 in Hotel Lobby Display Car (1987)


This next story is the stuff of racing legend.
It all started with a Thursday practice session, when Penske driver Danny Ongais crashed and suffered a concussion. In a bid to save the team’s Indy 500 championship effort, Penske team owner Roger Penske decided to call up Al Unser – of the four previous years Unser drove for Penske, he won three Indy 500s, so the choice was obvious. Unser agreed to fill in, but the team still needed the most important ingredient – a car. Luckily, they had a backup.
Meanwhile, across the country, in the lobby of the Sheraton Hotel in Reading, Pennsylvania, a 1986 March-Cosworth was being proudly displayed: the team’s backup. Yes, Roger Penske did indeed pull a display car from a hotel lobby and run it in the Indy 500.
Starting from 20th place, Unser worked his way to the front of the pack and took the lead on the 183rd lap, after leader Mario Andretti experienced engine trouble.
Just five days before his 48th birthday, driving a car taken from a hotel lobby, Al Unser won this fourth Indy 500.
Racing legend, indeed.
5. The Indianapolis 500 that Almost Didn’t Happen, and The Virtual IndyCar Scandal(s) That Did (2020)
The story of the 2020 Indianapolis 500 begins the same as just about every other story that takes place in 2020: the COVID-19 (Coronavirus) pandemic.
Tradition dictates that the Indianapolis 500 is run on or around Memorial Day each year – a tradition that has been held for its entire 110+ year history (except during both World Wars, when the race was canceled entirely). However, due to COVID-19, that tradition would be broken for the first time.
With the race rescheduled indefinitely and world morale on a collective low, IndyCar announced the formation of the “IndyCar iRacing Challenge” – a new iRacing series featuring drivers from the real IndyCar grid competing virtually on the simulator. The series also included fan favorites from other motorsports such as avid sim racer and McLaren driver Lando Norris (F1), and NASCAR drivers Jimmie Johnson, Kyle Busch, and Dale Earnhardt, Jr.
Here’s where the scandal (and heartbreak) comes in. One of the favorites to win the race was McLaren F1 driver Lando Norris, due to his extensive experience on iRacing. Lando himself even stated that he’d “never worked harder preparing for a race”, as he’d never driven ovals before and had to basically learn that skill from the ground up.
The race was exciting, but mostly uneventful, with a few racing incidents here and there. With 8 laps remaining of the 70-lap race, Lando was running third, behind reigning Indy 500 champion (at the time) Simon Pagenaud and Graham Rahal who were battling for the lead. Norris had the faster car with fresher tires and less damage, and made a move on the inside for a three-wide pass into turn one – for the lead. The move, which was pulled off cleanly on Norris’ part, caused Rahal to seize up and run up track and into the wall, collecting Simon Pagenaud in the process; and ending his hopes for the top step of the podium. A small mistake on Rahal’s part, but one Pagenaud pinned completely on Norris. Pagenaud decided to take revenge.
After announcing to the viewers of his stream (which ended up deleted shortly afterward) as he pulled out of the pits from his repairs that he was going to “take Lando out”, Pagenaud found himself positioned to do just that – deliberately dive-bombing Lando on the start/finish straight while he was leading the race.
Ironically, another McLaren driver, Oliver Askew, was crashed out as he was about to pass the finish line on the last lap of the race (while in the lead) by Santino Ferrucci (who was banned from F2 for deliberately crashing into a teammate). Ferrucci also ratted himself out on-stream and went on to delete the video, saying “it was worth it” and “it’s just a game.”
Takuma Sato went on to win the real-life (rescheduled) Indy 500, beating out Simon Pagenaud to his second career Indianapolis 500 win.
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