Wednesday evening was like living in a historian’s dream world for me. There I was in Easton’s oldest public building presenting a PowerPoint presentation of a race that last ran one hundred and fourteen years ago with two, one hundred-plus year-old Connecticut built vehicles sitting right outside that had been driven to the event under their own power! It really doesn’t get a lot better than that when your passion is sharing history with members of your community.

Alex Dragone, of Dragone Classic Motor Cars, answers queries about his 1923 Locomobile.

I first became interested in the history of the Sport Hill races when I was about twelve years of age. My father was then the vice president and general manager of the Blue Ribbon Garage in Bridgeport. The company began its long life as a manufacturer of wagons and carriages, later transitioning to building automobile bodies right after the turn of the century. The original building on Cannon Street was constructed sometime in the 1880’s and took up most of the block between Broad Street and Harrison. The upper floors were covered with thin wooden boards that creaked when cars were driven over them. Heavily stained with motor oil, the floors even bore a few tire impressions from vehicles that had once sat in one location for too long.

Part of the 1908 official race program for the Sport Hill Races

By 1905 the company had become the distributor of Packard automobiles for all of Fairfield and New Haven Counties. For at least two years prior to 1910, they also sold Cadillacs, and when the Dodge brothers introduced their own brand of automobiles in 1914, Blue Ribbon also became the sole distributor for all of Fairfield and New Haven Counties.

In 1908, the company constructed a 3-story, all-steel and concrete building on Fairfield Avenue that could hold up to 500 automobiles. It was advertised as the largest fireproof garage between New York City and Boston. The company was also one of the sponsors of the races that were held each year at Sport Hill, purchasing the entire rear cover of the race program at least twice during that time.

This advertisement was from 1911. The first ads showing this image in 1908 stated that it was the “only” fireproof garage between New York and Boston.

I loved to explore that old building. There were sleeping quarters on one of the upper floors where the chauffeurs of early cars could rest while their employers enjoyed a relaxing stay at one of the nearby hotels. While encased in a layer of heavy dust by 1960, the rooms were still perfectly preserved. Remnants of ceramic tiles were still visible in some of the service bays where vintage Packards and Cadillacs were once serviced. There were even two working, but rather ancient, service elevators that took automobiles from the ground level to the floors above. But the most intriguing thing I ever discovered in that old building was a six- or seven-inch-thick leatherbound scrapbook packed full of newspaper and periodical clippings that dated as far back as the late 1890’s, all of which described the activities of the garage, its employees, or any automobile related events in the greater Bridgeport area.

1909. A team competing in the Munsey Reliability Run that year chose the Blue Ribbon Garage as a place to spend the night. The facility had sleeping quarters designed for more traditional chauffeurs to overnight, but they obviously made an exception for this motley looking crew!

It was in that scrapbook, where I first learned about the annual hill climbs held in Easton. What I saw was fascinating. Nationally renowned drivers piloting some early, incredibly rare automobiles up the treacherous old road that led to the top of Sport Hill.

That scrapbook held many accounts of events that had been held in Easton about fifty years earlier. Luckily for me, I was still able to ask a few questions of some of the old timers, such as my grandfather and his brothers who had lived in Easton during those years. Gramp’s older brother, Rob, had even been mentioned in one of those old newspaper clippings, as it was his house that sat closest to the finish line and the place where the course referees would meet in the morning prior to the start of the day’s races.

Over the course of many years, I gradually amassed a collection of old clippings and postal cards that depicted the annual events held in Easton. About a dozen or so years ago, I stumbled upon a rather large collection of photographs – all correctly labeled – that had been taken by the Spooner and Wells studio in NYC. They included many of the photos from 1909 and 1910 we put into our PowerPoint presentation this week. All had been donated to the Detroit Public Library and are now in their digital collection.

The Staples Free Academy building was built in 1795. With funds bequeathed by Samuel Staples, the academy was established for the purpose of providing a high level of education to deserving children regardless of their ability to pay. The Staples Free School was only the second free private academy established in the United States, preceded only by Phillips Exeter Academy in New Hampshire.

After a long run as a place of learning, first as a private institution and later as a public elementary school, in 1937, the Staples Free Academy building became the property of the Congregational Church of Easton across the street. Since that time, it has served as the Church Hall and offices. A 1960’s addition provided the Congregation with a large meeting room/hall and a modern kitchen for preparing food for almost any size event.

The Staples Free Academy building in 1937 about the time when the Easton Congregational Church took possession of it.

Comfortably accommodating up to sixty seated guests, the Church Hall is the perfect venue for hosting the cooperative Old Academy Lecture Series, a collaborative effort between the Historical Society of Easton and the Congregational Church of Easton which still owns the building. These lectures are a good example of how community organizations can work together to the mutual advantage of both parties. The Society benefits from having a well-equipped, centrally located venue, and the Congregation benefits from hosting an organization capable of producing a quality presentation that exposes their facility to members of the community who may have previously never known about it.

A full house on Wednesday, November 13th, when we gave our presentation, “Uphill Battles, the History of the Sport Hill Races.”

Wednesday night’s event drew a full house. Both the Church and the Society no doubt benefited from the addition of those two classic automobiles that were parked in front of the building. We offer our great thanks to Shenton King, who drove his beautiful 1912 Pope-Hartford Touring car over from Redding. Shenton is the current president of the Fairfield County chapter of the Horseless Carriage Club of America, https://www.facebook.com/groups/119087132480. We are also extremely grateful to Alex Dragone from Dragone Classic Motor Cars in Orange for gracing us with his beautiful 1923 Locomobile Model 48 Touring car, https://www.dragoneclassic.com/. Alex drove in from Orange, even daring to take the Merritt Parkway in his 101-year-old machine! Both these vehicles were manufactured right here in Connecticut; the Pope in Harford, and the Locomobile in Bridgeport.

Historical Society presenters Bruce Nelson and Elizabeth Boyce along with Shenton King and his 1912 Pope-Hartford Touring car.
Some of the Sport Hill Race memorabilia that the Historical Society of Easton manages.
Historical Society presenters Bruce Nelson and Elizabeth Boyce standing alongside Alex Dragone and his Bridgeport built 1923 Locomobile Model 48 Touring car. Alex drove his 101-year-old machine to our event via the Merritt Parkway!

I would also like to offer my personal thanks to my friend and colleague, Elizabeth Boyce for moderating the event and curating the Society’s collection of Sport Hill Race memorabilia for all to see and enjoy. Thanks also go to Don Boyce for putting this series together, and the members of the Congregational Church of Easton for their tireless efforts to supply the audience with a delicious spread of treats during every event.

Be on the lookout for the next event in the Old Academy Lecture Series. Hopefully, we’ll see you there!

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