No one can say for certain how the southern part of the old Jackson Highway came to be named Sport Hill. While some would attribute it to the auto races held there during the first decade of the twentieth century, that name preceded those events. The more likely origin would have come from friendly competition amongst younger folks who availed themselves of the steep incline for sledding and tobogganing during the late 1800’s.

In 1900, the Sport Hill section of the Jackson Highway was a formidable piece of highway that clung to the side of a rocky cliffside to the west. It was steep, surfaced largely with dirt and rocks, and presented somewhat of a challenge to teamsters passing in opposite directions on some of the narrowest and sharpest turns. Unlike today’s long and mostly straight incline that rises from the Mill River crossing at the Easton/Fairfield town line, the old Sport Hill crossed the river a bit farther to the west and then wound its way up the hill following today’s “Old Sport Hill Road.”

In total, there were barely more than a dozen houses along that section of Jackson Highway between the Fairfield town line and Flat Rock Road that year. The only intersection along that stretch of highway was Delaware Road, there were no other side streets. The state hadn’t yet begun to issue license plates for motor cars – there were barely enough to count, and in a town as small as Easton, there wasn’t a single resident who owned one at the turn of the century.

I’d venture to say that automobile racing began the very first day that two men found themselves operating their new horseless carriages headed in the same direction on the same road.

Early racing began mostly on public byways. The owners of most horse racing venues weren’t particularly fond of the thought that racing those obnoxious motor cars might soon replace the sport of kings.

While it is safe to say that the general public was fascinated by these new machines, it is also a pretty sure bet that most folks thought those noisy and expensive toys were not destined to replace the horse anytime soon. Outside of the city limits, most roads were not well suited to motorized transportation. Unpaved, often muddy, never plowed during the winter months, rural roads were inhospitable to these machines except during fair weather and dry times.

Horses basically ran on water and oats. Automobiles required either electricity or gasoline. Steam powered automobiles required less gasoline as they only needed enough fuel to feed a small fire that boiled the water that produced the steam, but they still needed a fuel source that was commercially produced and distributed. Both gasoline and electricity were rare commodities out in the country, so most folks were dismissive of the idea that there was a motorcar in their future.

Besides the obvious entertainment of watching grown men risk their lives by going faster than other grown men piloting similar machines, auto racing was seen as a way by early manufacturers to promote their product.

During the glory years, the Sport Hill Races were a well-attended, well covered event that took place every Decoration Day (Memorial Day). Between 1907 and 1909, thousands of spectators lined the course and many of the entries were sponsored by the automobile manufacturers of the day. Some of the drivers were the among the best in the profession and competed both in the United States and Europe.

But when exactly was the first race run?

The answer is 1902. This was long before Detroit would become the epicenter of automobile manufacture. With the exception of one entry built in France, all of the automobiles that competed in that first hill climb at Sport Hill were either built in Connecticut or Cleveland, Ohio.

Bridgeport was one of the most industrialized cities in the East that year. There were more than a few well-heeled businessmen who could both afford to purchase an automobile and who were daring enough to try their hand at racing one. While the number of automobiles in Bridgeport surely numbered well under one hundred in 1902, a good many of the men who owned one formed a club aimed at promoting their use. The men of the Automobile Club of Bridgeport wasted no time in coming up with the idea that racing one another against the clock would be both a good challenge and a way to show off their new toys.

It is unknown exactly how Sport Hill was chosen, but the logistics and the terrain made sense. Close to Bridgeport, a challenging course, few houses along the route, and only a single intersection along the one-mile route from start to finish. Whether the club sought anyone’s permission to race there that day is not clear. But race there, they did.

There were eight entries by seven different owners. DeVer Howard Warner was the secretary/treasurer and the son of founder Doctor Ira DeVer Warner of the Warner Brothers Company, a manufacturer of corsets in Bridgeport. Lewis B. Curtis was the vice president and treasurer of Curtis & Curtis, a manufacturer of pipe cutting machinery on Railroad Avenue. Jesse Banks Cornwall was the president of Cornwall & Peterson, a manufacturer of piano and organ hardware on Fairfield Avenue. Ernest V. Sloan and Herbert A. Budlong were the head engineer and plant manager of the American Graphophone Company. Jonathon Godfrey was the owner of the Compressed Paper Box Company and Miles V. Doud headed the sales department at Locomobile, the Bridgeport based manufacturer of three of the motor cars entered that day.  

Curtis and Warner entered their Cleveland built Wintons. Godfrey raced his Peerless, also a product of Cleveland. Budlong’s gasoline powered Columbia had been built in Hartford. Doud drove two of his company’s Locomobile steamers, while Sloan competed with a third steamer from the same manufacturer. The lone foreign entry was a de Dion Boughton built in France and piloted by Jesse B. Cornwall.

The steam cars proved to be astonishingly quick. The fastest machine of the day was piloted by Sloan, a mechanical engineer by profession, who got his Locomobile to the finish line in 2:45, for a speed of 22 mph! If you think that is slow, take a look at what he was driving. Steered with a tiller, the steam carriage had a single brake at the left rear wheel!

1902 Locomobile steam powered motor carriage.

Cornwall’s de Dion posted the fastest time of the lighter gasoline powered vehicles – alas, his car was the only one in that class and it was by far the slowest entry. He made it to the finish line in 9:09, with an average speed of 6.56 mph. Faster than walking, but not by very much. Cornwall would subsequently purchase Locomobiles exclusively.

Easily the best looking of those first racers at Sport Hill, but the 1902 de Dion Boughton was also the slowest by far.

The fastest heavy gasoline powered machine of the day was piloted by Curtis. His Winton crossed the finish line in 4:97, recording an average speed of 10.68 mph.

1902 Winton. More sophisticated than most vehicles of that era, but still slow.
1901 Columbia Gasoline. Columbia also built electrically powered machines.

The racing improved greatly during the the subsequent years, but as Easton began to grow along with the crowds, the event fell out of favor with the residents living along the course. It didn’t help that as more and more daring young men became the proud owners of motor cars that they took to racing up Sport Hill on a regular basis. By 1909 the magic was waning and the last race in Easton took place in 1910, but on Snake Hill on Burr Street, not Sport Hill.

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By Bruce Nelson

Director of Research for the Historical Society of Easton Town Co-Historian for the Town of Redding, Connecticut Author/Publisher at Sport Hill Books