1821 Montgomery County organized. County seat site three miles southwest of Hillsboro selected March 21 and site named Hamilton on April 23.
1822 Robert Anderson and Milton Shurtleff secure permits to sell liquor and other articles.
1823 Commissioners select Hillsboro for new county seat. George File, surveyor, receives $3.75 for laying out town lots.
1824 Contract of $221.83 awarded to Thomas McAdams for building courthouse. Commissioners give free lots to Joseph and Benjamin Miller for tan yard.
1825 Erect log house on hill west of Central Park for school and church. John Tilson builds brick house on northwest corner of Main and Tremont streets.
1826 Commissioners order stairway built between first and second floors of courthouse.
1827 Israel Seward appointed assessor at $17 per year.
1828 Commissioners contract for first jail. Meeting at John Tilson's house to organize Presbyterian church.
1829 Hiram Rountree receives $20 for six months' service as county and circuit clerk.
1830 Stephen Fullingsworth appointed keeper of stray pen for wandering livestock.
1831 Hiram Rountree builds brick house on corner of Rountree and Wood streets. Presbyterians erect first church building.
1832 Two Hillsboro companies leave for Black Hawk war. St. Paul's Lutheran church founded and services held in courthouse.
1833 Thomas Whitten contracts to build frame courthouse for $1,800.
1834 Population of Hillsboro placed at 250. Methodists and Lutherans erect their first church buildings.
1835 Hillsboro streets opened "sufficient width to permit passage of wagons and carriages." Frame courthouse given two coats of paint.
1836 John T. Maddux, first mayor, settles in Hillsboro. Village grants license for first show, a zoological display.
1837 Academy opens. County commissioners seek loan of $600 to build three bridges across Shoal Creek.
1838 First newspaper, the Prairie Beacon, published by Aaron Clapp.
1839 First Masonic Lodge organized.
1840 Methodists build second church.
1843 Organize Oak Grove Cemetery Association.
1844 Lincoln speaks from courthouse.
1846 Company of ninety-six men leaves for Mexican War. Lutherans acquire Hillsboro Academy.
1847 First county poor farm established in Irving Township.
1848 First Odd Fellows' Lodge organized.
1849 Six thousand attend railroad convention and barbecue.
1850 Rev. Francis Springer edits the Prairie Mirror.
1851 Citizens of Hillsboro and Montgomery county vote to purchase $50,000 stock of the Terre Haute and Alton R. R. Co.
1852 Lutherans move college to Springfield but Academy continues at Hillsboro.
1854 Hold first county fair. Frame courthouse replaced by two-story brick.
1855 Railroad reaches Hillsboro. Hillsboro becomes incorporated town with Thomas Phillips as president of the board. First ordinance prohibits the running of animals at large.
1857 County Medical Association holds first meeting. Lutherans erect two-story church building.
1858 Telegraph line completed. Stephen A. Douglas and Abraham Lincoln speak at fairgrounds. Lincoln is guest of Joseph Eccles. School teachers hold first county institute.
1859 Pike's Peak gold rush takes many from Hillsboro to Colorado. Davis, Haskell, and Clark open first bank. Independent Light Guard Company, with R. W. Davis as captain, formed.
1860 Presbyterians build new church.
1861 Military companies leave for war service. North School is erected.
1865 Citizens meet at courthouse to celebrate close of Civil War. Congregational church is built.
1867 Louis Welge opens furniture factory. Clotfelter Building and Masonic Mail are erected.
1869 Hillsboro incorporated as a city and John T. Maddux elected mayor. First test for coal is made. Glenn mills ship sixty cars of flour and grain. St. Agnes Church is erected.
1870 Montgomery County Bank &Trust Company, organized in 1869, opens for business. Courthouse remodeled.
1872 Union Block building erected.
1874 Site for county poor farm selected. Amos Miller and Judge E. Y. Rice form law partnership.
1880 Academy discontinued and building used for public school.
1882 Hillsboro National Bank organized. Merchants incorporate Commercial Club.
1883 Old Settlers' Association formed. Hold first high school commencement.
1885 Merchants fight removal of wooden awnings.
1886 Edward Lane elected to Congress.
1887 Coal mine completed. Company to promote mineral springs formed. Edison School and Opera House built.
1888 Pump house and water tank erected. Schedule of water rates fixed.
1889 City ordinance makes possession of slingshot a misdemeanor. Organize Hillsboro Township Fire Mutual Insurance Company,
1890 Free Methodists dedicate church building. Cress Hill Cemetery Association buys burial ground from Lutherans.
1891 City grants franchise for light, heat, and power.
1892 Ordinance prohibits barbed wire fences near walks. C. W. Bliss becomes owner and editor of Montgomery News. C. A. Ramsey elected to state legislature.
1893 Hillsboro obtains first electric lights.
1894 John M. Whitehead and Amos Miller erect Corner Block Building, John R. Challacombe elected to state legislature.
1895 Reading room opened. Telephone system begins with twenty-five telephones.
1896 Empire Mill on Vawter Street destroyed by fire.
1897 Thomas Jett elected to Congress, first of three consecutive terms. Lutherans dedicate new church.
1898 Company E leaves for Springfield en route to Spanish-American War.
1899 Miss Margaret Williams employed as music instructor for Hillsboro schools.
1900 Post office begins rural delivery.
1901 Businessmen meet to promote lake and new water supply. Creamery receives 3,000 pounds milk daily.
1902 Mutual Telephone Company organized.
1903 Methodists dedicate new church structure. City Council requests curfew ordinance. Contract is let to Challacombe and Minton for lake dam.
1904 Second railroad reaches Hillsboro. Kortkamp mine opened. Students enter new high school.
1905 Peoples National Bank organized. Library opened to public. Roundhouse and turntable for railroad are built.
1906 Schram glass factory begins manufacture glass jars and glasses. Electric interurban reaches Hillsboro. First Litchfield-Hillsboro Chautauqua program given.
1907 Track laid from courthouse to depot for city electric streetcars. South Main Street paved.
1908 Taylor Springs mine opened. County jail and sheriff's quarters built.
1909 Congressman Jett elected circuit judge, and serves in that capacity until his death in 19.39.
1910 Worst hailstorm in history of Hillsboro does severe damage to buildings on April 15.
1911 American Smelter at Taylor Springs, and Robert Lanyon Smelter at Hillsboro build plants. City adopts commission form of government.
1912 City mail delivery established.
1913 City installs fire siren at light plant. Evans Brothers buy auto ambulance. Moose Club organized.
1914 High school wins state basket ball championship. Hillsboro Woman's Club organized.
1915 Build Burbank School. State Senator S. D. Canaday serves as Acting Governor of Illinois during absence of Governor Edward F. Dunne and Lt. Governor Barratt O'Hara.
1916 Hillsboro Hospital dedicated. Winhold Parent Teachers' Association organized.
1917 Hillsboro men leave for World War. Work on new City Lake begun.
1918 Farmers meet at Hillsboro to organize Farm Bureau.
1919 Company E and other soldiers return from France.
1920 City pays $9,000 for first auto fire engine. Sheriff M. T. Kiggins begins raids on illicit stills. Women cast first general vote.
1921 New community high school opened. Fire destroys packing room of glass factory. Robert Zuppke, Illinois coach, addresses newly formed Montgomery County mini Club. William Jennings Bryan speaks at Chautauqua.
1923 National Guard called for labor trouble at American Smelter. Taylor Springs mine closed. Rotary Club formed. Hillsboro Country Club opened. Former Hillsboro orphan, Harry Ferguson, returns as "Prince Obolensky".
1924 Christian Church dedicated. Kortkamp mine closed. Big Four subway completed. Harold Osborne wins Olympic Decathlon in France.
1925 Schram Glass factory sold to Ball Brothers. Route 16 between Irving-Hillsboro-Litchfield completed.
1926 City water works built. Sheet and pillow-case factory opened. Fire destroys A. H. Bartlett garage and American Express office. J. Earl Major elected to Congress, first of three terms.
1927 Light and power company replaces street cars with buses. Old Blockburger Inn torn down for service station, Trans-Atlantic telephone service available, $78 for three minutes.
1928 Frank M. Ramey elected to Congress.
1929 Fire sweeps light and power office and American pants factory. Route 127 completed to Hillsboro.
1930 Thermometer registers 20 below on January 18, and 112 on July 28. Ben Wilton sells Lincoln furniture to Henry Ford for Dearborn Village. Banks closed at Donnellson, Nokomis, Rosamond, and Fillmore. Population of Montgomery county placed at 35,268.
1931 Final Chautauqua program given. Fire destroys St. Agnes Church. Newton Coffey heir claims title to original site of Hillsboro but Coffey deed shows land given to county "forever." Peoples Bank and Taylor Springs Bank absorbed by Montgomery County Loan & Trust Co.
1932 Overhead bridge south of Hillsboro opened. Beatrice Imhoff elected "Miss Illinois" at State American Legion convention. Fire destroys Old Settlers' cabin at Junior High School.
1933 All banks close for national bank holiday. Blue eagle of N, R. A. appears as merchants conform to new act. Pay checks go to unemployed under new C. W. A. plan.
1934 New Post Office Building completed. Citizens vote to continue commission form of city government. First airplane accident in community takes lives of Allen Harwood and John Mikeska.
1935 C. E. I. passenger train wreck kills live, injures many. W. P. A. projects begin in county. Kiwanis Club receives charter.
1936 City builds P. W. A. sewage disposal plant and Central Park Swimming pool. New city hall erected.
1937 Hall Brothers rebuild glass factory. Ordinance prohibits the keeping of hogs in city limits. New city jail built.
1938 Business men work for proposed veterans' hospital. City sells water to Big Four Railroad.
1939 High school gymnasium, new water tower, and filtration system at swimming pool completed. Build all weather roads to Fillmore, Walshville, and Raymond. One killed, six injured as dynamite blast levels two story flat and shatters windows in business area. J.T. Bullington elected circuit judge.
Taken from Hillsboro Guide 1940