History

The first party of pioneers who considered settling in Oswego decided to take a pass. They were among the last to do so.

In the early spring of 1831, brothers George and Clark Hollenback, and their friends William Harris and Ezra Ackley, had worked their way up the Fox River from Ottawa looking for a likely spot to settle. They camped for one night at about the spot where downtown Oswego is located today, and in the morning, George Hollenback took a stroll, liked what he saw, and decided it would be a good place to settle.

Lewis B. Judson, the man credited with establishing the Village of Oswego, arrived from Michigan in the fall of 1834. He bought the claims of several settlers who had preceded him to create a holding of nearly 800 acres that included all of the original Village of Oswego. The next year, Judson and storekeeper Levi Arnold laid out a new town they named Hudson on property Judson owned.

The small settlement grew quickly, and in 1837, the new town got a real prize, a post office. For some reason, the U.S. Postal Service named the post office Lodi, so the growing village had two names: Hudson and Lodi. The town fathers gathered and decided a single, permanent name was needed. When the votes were tallied, Oswego won by a single ballot.

Situated at the intersection of roads from Chicago to Ottawa, Joliet to Dixon, and Ottawa to Geneva, Oswego’s growth was faster than other communities in Kendall County. Although Yorkville was picked as the first county seat in 1841, the voters approved moving the courthouse to Oswego in 1845. But in 1864, the courthouse moved back to Yorkville.

From the end of the Civil War until the end of World War II, Oswego served as the local market town for farms in the surrounding countryside. During the nation’s experiment with Prohibition, Oswego’s location on some of the major roads of the time, and its proximity to Chicago, reputedly made it a rest and relaxation area for some of the era’s most famous gangsters. John “Three Fingered Jack” Hamilton (so named because two fingers on one hand had been shot off during his career), fatally wounded in 1933 during the Dillinger gang’s escape from the Little Bohemia Lodge in Wisconsin, was hastily buried in a shallow grave near Ill. Route 25 just north of town. The FBI recovered his remains in 1934, and reburied them in the Oswego Township Cemetery, the village’s sole remaining tie to that boisterous era.

Although previously known mostly as the mercantile center for the farming area that surrounded it, in 1955 Oswego became home to something that spread its name nationwide. That summer, Dan and Wally Smith, co-owners of the family farm rented to the Cutsinger family, agreed to plow under several acres of crops to create a drag strip. The Cutsingers’ sons, Dale and Darold, were enthusiastic hot rodders who encouraged the strip’s formation. That summer, as many as 120 hot rod owners raced each week on the dusty dirt strip. At the end of the season, the Smiths decided to take out a loan to have the strip paved with asphalt. The new and improved Oswego Drag Raceway opened Easter weekend of 1956. It was a community institution and auto-racing destination for the next 23 years. Weekly drag races drew an average of 2,000 racers and fans to the strip each weekend with up to 5,000 attending when some of the stars of the sport—including Art Arfons and Arnie “The Farmer” Beswick—raced there. This at a time when Oswego’s entire population was less than 2,000 residents.

Development took a breather during the 1980s, but in the early 1990s the Route 34 corridor began funneling growth to Oswego from fast-growing Collar County communities to the east. In 1990, Oswego’s population stood at just above 3,800 residents. Ten years later, more than 13,000 residents called Oswego home. Today, well over 30,000 residents live inside Oswego’s municipal limits.  With the area’s growing population came accelerating commercial growth.

George Hollenback had the right idea back in 1831, and his exploring party appears to have been one of the last groups to decide to take a pass on Oswego. As the prosperous, growing community past the 175th anniversary of its settlement, it’s likely the village’s first settlers would be proud of what they started when they began their new lives on the Illinois prairie in the Year of the Early Spring.