Materials collected from the Kendall County Record; The History of Kendall County, Illinois by the Rev. E.W. Hicks; various issues of the Oswego Herald; 150 Years Along the Fox: The History of Oswego Township, Illinois by the Oswego Sesquicentennial Steering Committee; and primary and secondary source materials in the Oswego’s Little White School Museum collected by the Oswegoland Heritage Association.
1833: William Smith Wilson arrives to settle Oswego. He builds his first home near the intersection of the East River Road and the Chicago Road—today’s U.S. Route 34 and Ill. Route 25 intersection.
1835: Levi Arnold and Lewis B. Judson lay out their village of Hudson. Arnold builds the first store, located, according to Hicks’ History of Kendall County, Illinois, at 68 Main Street.
1837: Oswego is awarded a post office and gets its permanent name through popular vote. Aaron and S.L. Bartlett build the small home along the west side of Main Street at Bartlett Creek.
1838: James Reed, a contract surveyor working for Assistant U.S. Surveyor Eli Prescott, surveys the site of Oswego—and the rest of Oswego Township—in the summer months. Reed reports Oswego boasted “20 or 30 wood buildings.”
1841: Kendall County established by taking six townships from LaSalle County and three from Kane County.
1842: First survey map of Oswego Township published by the U.S. Government, with information from James Reed’s field notes.
1845: Kendall County seat moved to Oswego. First term of the Circuit Court held in the National Hotel on Main Street while the new courthouse is being built.
1848: The new Kendall County Courthouse is completed on the block bounded by Madison, Jackson, Monroe, and Jefferson streets—site of today’s Oswego Post Office, Oswego Community Bank, and Village Green Park.
Also, the first bridge, consisting of two timber spans, is built across the Fox River.
1849: M.A. Fenton operates the Oswego Post Office in the building Henry Helle would one day purchase at Jackson and Main (see brief history of Oswego Post Office in Feb. 10, 1897 Kendall County Record).
1850: Oswego Methodist-Episcopal Church (Little White School) is completed.
Also opening this year is a new public school at Monroe and Tyler streets. The school is built of native limestone and includes both elementary and high school grades. It replaces an old frame school building at Madison and Van Buren Street. Eventually, it becomes known as the Old Stone School.
1853: The first railroad through Oswego Township—the Chicago Burlington & Quincy—passes about a mile and a half west of Oswego.
1855: Oswego is incorporated. The first village board members elected after Oswego was incorporated included John W. Chapman, Lewis B. Judson, John M. Crothers, Frederick Coffin and Walter Loucks.
1859: Kendall County voters decide to move the county seat back to Yorkville.
1860: Presidential election; Oswego votes Republican, helps elect Abraham Lincoln.
1861: Civil War breaks out. Torchlight rallies held at the Kendall County Courthouse and the National Hotel in Oswego.
1864: New Kendall County Courthouse in Yorkville completed. County records moved from Oswego in June.
1865: Civil War ends.
1867: An overheated stovepipe leads to a devastating fire in early February that burns down every building on the east side of Main Street from Washington Street north to Jackson Street. Losses include the stately National Hotel. Construction begins almost immediately on new brick buildings to replace the old frame structures.
The old timber bridge across the Fox River is badly deteriorated. Oswego Township builds the first iron bridge, a tied-arch structure manufactured by the King Bridge Company of Canton, Ohio, across the river at Oswego. Total cost: $5,000.
1870: The first black citizen to cast a ballot in Kendall County votes in the spring election for Oswego Township Supervisor John W. Chapman. The name of the voter, however, was not recorded.
In October, the Fox River Valley Railroad reaches Oswego. Eventually, it would connect Aurora with Streator.
1872: According to the Kendall County Record’s Oswego correspondent, the following businesses were located in Oswego this year: Woolenweber and Knapp, livestock; D.M. Haight, general store; E.A. Parke and Herman Tetzlaff, general; W.P. Hawley, general; Mr. Greenfield, furniture; Richards, Edson & Co., general; Levi N. Hall, apothecary; Lawrence Briggs, veterinarian; W.S. Bunn, lumber; Anton Miller, groceries; Coffin and Son, groceries; Henry Helle, boots and shoes; Mr. Sutherland, saloon and billiards; George Troll, saloon and billiards; M. Ivanchanden, barber shop; Mr. Seer, barber shop; Lorenzo Rank, postmaster, steamship line agent; H.C. Strothman, restaurant and confectionery; Drs. Van Deventer, Lester and Jewell; Fowler and Newton, Justices; A.P. Snick, F. Hawley, A. Snook, lawyers; Gus Voss, insurance; Armstrong and Snook, meat market; Newton and Armstrong, mfg. Wooden wares (pumps).
1874: Lorenzo Rank, Oswego Postmaster, builds a new commercial building on a portion of the site formerly occupied by the old National Hotel at 68 Main Street as the new location of the post office.
1878: Susan B. Anthony lectured in Oswego on April 1 at the Congregational Church.
1880: In August, the first bicycle glides through Oswego, the rider having pedaled down from Aurora.
1882: Street lamps are installed for the first time in Oswego. One was erected on the corner of Main and Jackson in front of Henry Helle’s store; the other one at the south end of the Main street block. The lamps, installed for a trial only, burned naphtha.
1884: The Kendall County Record’s Oswego correspondent reports on May 22 that “The frame of the new (township) Council building is up, on the south side of Washington street above the railroad tracks.”
1885: The Old Stone School is gutted by fire. Classes are moved to the former Kendall County Courthouse at Madison and Jackson until the end of the school term. In the summer, the courthouse is torn down and construction begins on a new school building that will be called the Red Brick School.
1894: In July, the stately Congregational Church on South Main Street at Benton Street burns. The church bell was said to have been cast in Chicago in 1849, the first bell cast in that city.
In October, the wooden sidewalks along the east side of Main from Washington to Jackson are removed and concrete sidewalks are installed.
1895: Oswego’s first water tower, 112 feet tall, is filled for the first time. It was located at the corner of Washington and Van Buren streets. The village also buys a fire hose cart with which to fight fires.
1896: The Evangelical Association finishes and dedicates their new church at Washington and Madison streets, now called the Church of the Good Shepherd.
1897: Telephone service is introduced throughout Oswego.
1899: In March, John Schickler begins construction on his new brick store block at the southwest corner of Main and Washington.
1900: Just a year after John Schickler begins construction on his new commercial brick block, it is seriously damaged by fire. Schickler rebuilds.
That spring, a new iron box-truss bridge replaces the old iron tied-arch bridge built in 1867 to carry the additional weight of the interurban trolley cars.
In October, the interurban trolley line reaches Oswego. The line extends from Aurora south to Yorkville.
1903: First black student to graduate from high school in Kendall County, Ferdinand Smith, graduates from Oswego High School.
1907: Robert Johnston’s new home at the corner of Madison and Chicago Road (Routes 34 and 25) was completed and the family moved in.
1911: The Burkhart Block at the southeast corner of Main and Washington is built. Tenants included the Oswego State Bank on the corner and the Oswego Post Office the next-door south. The third storefront was occupied by the Chicago Telephone Company for their switchboard.
1915: The Oswego School District acquires the Methodist-Episcopal Church building at Jackson and Polk streets for use as a school.
1917: Local barber Gus Voss and real estate agent John Herren combine to build a new brick commercial building at the southwest corner of Main and Washington streets.
1920: The Oswego Congregational Church burns for the second time. Members decide not to rebuild, but instead to combine with area Baptists, Lutherans and Methodists to establish the Federated Church using the Church of the Good Shepherd building. In December, the fire prompts the village to purchase their first fire engine, a Model T Ford chassis equipped with a chemical fire apparatus.
1922: Earl Zentmyer, a young Aurora mechanic, buys the Liberty Garage at Main and Jackson Street in downtown Oswego (today’s American Male & Company building) from H.B. Reed and begins his business career in Oswego.
1928: Dr. Lewis Weishew builds the first portion of the medical clinic at the corner of Main and Van Buren in downtown Oswego using Joliet limestone.
1930: On May 7, it is reported Alexander Lumber Company of Aurora has bought the Oswego Lumber Company, and plans to operate it at the same location.
1937: The 1900 iron box truss Oswego bridge is replaced with a new steel and concrete structure by the State of Illinois. The original bridge piers are reused.
1940: Lewis Chrisse builds a concrete block farm implement dealership (today’s Oswego Industries building) at the corner of Washington Street and Ill. Route 71.
1950: The Oswegoland Park District is organized by popular vote.
1951: The new Oswego High School at Franklin and Washington streets (now Traughber Junior High) opens.
1953: Oswego Fire Station One is completed on the west side of Main Street just south of Jackson Street.
1954: The first services are held at St. Anne’s Catholic Church on Washington Street in Oswego. Today the building is known as the Knights of Columbus Club.
1957: East View School opens in Oswego. It is the first new school to be built solely for elementary purposes in Oswego since 1850.
1958: The new Oswego Community Bank opens at 55 Main Street in downtown Oswego in August. The building is now part of the American Male & Company building. The first president was Earl Zentmyer, also owner of Zentmyer Ford in Oswego.
The village board votes to finance installation of new streetlights along Main Street in the downtown business district. Previously, there were only two streetlights downtown, one at Main and Washington and one at Main and Jackson. Both lights were suspended from cables in the middle of the two intersections.
1964: The new Oswego Library opens at Main and Jefferson in downtown Oswego. The building was financed through private donations arranged by the Nineteenth Century Club and other community boosters.
A new, larger Oswego High School opens on a site opposite East View School along Ill. Route 71, in Oswego on land formerly owned by the Gerry family. The old high school on Franklin Street is renamed Oswego Junior High School.
1965: The Zentmyer Ford dealership at Main and Jackson Street in downtown Oswego, now owned by Jim Zentmyer, Earl Zentmyer’s son, is completely destroyed by fire. The dealership was housed in the historic old Shoger livery stable building.
The old Red Brick School is demolished to make way for a new Oswego post office building and the Oswego Community Bank’s new location.
The Oswego Presbyterian Church opens its new building on Ill. Route 25 just north of Oswego. They sell their old building at Madison and Benton Street to the Oswego Baptist Church.
1968: Shuler’s Drug Store moves to their new commercial building at the northeast corner of Main and Jackson Street in downtown Oswego, the former location of Zentmyer Ford.
St. Anne’s Catholic Church dedicates their new church building on Boulder Hill Pass near Oswego’s new Windcrest Subdivision. The striking, modernistic structure quickly becomes an area landmark.
1970: In July, the Oswego Community Bank breaks ground for their new bank at the corner of Jefferson and Madison Street on the former location of the Red Brick School.
1971: In February, fire does $40,000 worth of damage to Shuler’s Drug Store in downtown Oswego.
Although efforts are underway by the Oswego Jaycees to turn it into a community museum, the old Chicago Burlington & Quincy Railroad depot on Jackson Street at the railroad tracks is demolished.
A new commercial and apartment building—the Wilhelm Building—is built at Jefferson and Main Street housing retail stores on the first floor and apartments on the second floor.
1972: The first, large-scale downtown improvement project is completed when mansard-style roofs are installed on several downtown buildings.
1973: Fire destroys two buildings on the west side of Main Street housing the Oswego Ledger office and the Oswego Home Center. The buildings, built in 1867 following the fire that February, are later replaced by a modern office and apartment building.
1976: To provide additional downtown parking, a municipal parking lot is installed behind the fire station on Main Street. A portion of the property at Jackson Street was once the site of the Oswego railroad depot.
1980: On April 1, new traffic signals are turned on for the first time at the intersection of U.S. Route 34 and Ill. Route 71 in Oswego.
1981: The last grocery store to operate in downtown Oswego, Bohn’s Food at 60 Main Street, closes. The store is converted into an office building.
1988: Oswego annexes west as far as the intersection of U.S. Route 34 and U.S. Route 30. Illinois FIRST grant money is used to extend water mains to the intersection.
1989: Townes Crossing Shopping Center at Douglas Road and U.S. Route 30 opens, with a Jewel-Osco Store as its main anchor.
Also opening that year was the Oswego Plaza Shopping Center at Ill. Route 71 and Washington Street.
1990: For the first time in the village’s history, it annexes land on the west side of the Fox River.
1991: Oswego hires its first full-time village administrator, Mary McKittrick.
1993: The Illinois Department of Transportation completes a new four-lane bridge carrying U.S. Route 34 across the Fox River at Oswego. The old bridge is to be retained as a bridge-park
1994: Ill. Gov. Jim Edgar comes to Oswego to help dedicate the Hudson Crossing Bridge Park, the old Route 34 bridge across the Fox. Instead of demolishing the old bridge, it was refurbished and dedicated to the Oswegoland Park District for use as a pedestrian, fishing, and bicycle bridge.
In December, traffic signals are installed at Washington Street and Ill. Route 71.
1995: Widening begins on U.S. Route 34 from Ill. Route 71 to Ill. Route 31 in Oswego. The Illinois Department of Transportation project will widen the road to four lanes, including curbs, gutters, and sidewalks along the entire length.
1996: Construction starts on the Mason Square Shopping Center at Douglas Road and U.S. Route 34. Shopping center developer Harold Oliver names the center after his son, Mason.
2000: Shuler’s Drug Store closes. For the first time since the village was founded, there is no drug store on Main Street.
2001: a two-year project to replace and renovate streets and other infrastructure in downtown Oswego begins. The project included complete replacement of Main Street from Jefferson to Van Buren Street, along with new sidewalks, additional parking, improved street lighting, and other improvements.
Oswego Commons Shopping Center on U.S. Route 34 at Douglas Road opens, anchored by a Dominick’s Fresh Store, a Target department store, and The Home Depot.
2004: The first new high school in 40 years opens on a 100-acre site at Harvey and Wolf roads on Oswego’s far east side. For the first time in Oswego’s 160-year history, the community will be served by two high schools. The school board names the new building Oswego East High School. It is built for an eventual enrollment of 2,400 students.
Oswego Village Board approves a historic preservation amendment to the village zoning ordinance.
2005: the U.S. Bureau of the Census names Oswego the second fastest growing community in the nation. Since 2000, the community’s population has grown by more than one-third. Illinois is, in percentage terms, the fastest growing county in Illinois.
The historic Helle Building at Main and Jackson Street in downtown Oswego is demolished to make way for a new three-story commercial building.
Construction begins on a three-story commercial and office building at Washington and Harrison Street. The building is planned to be the home of a brewpub on the first floor and offices on the other two floors. Parking is to be located across Harrison Street to the west, where the old Oswego Public Works garage is to be torn down.
In addition, approval is given for more shopping centers along the U.S. Route 34 corridor east of Douglas Road, including a center anchored by a Wal-Mart Superstore and another center anchored by a Meier Store.
The village board grapples with whether Oswego’s most important historical structures ought to receive landmark status even if the property owner objects.