| Headline | Month | Day | Year | County | City |
|---|
| Corrections to obituary of Col. E. A. Calkins | | | No Year | | | View |
| Historians, old news files show March 4, 1856 as city's birthday | | | No Year | Dane | Madison | View |
| Old settlers | June | 11 | 1881 | Dane | Madison | View |
| State pioneer association | April | 20 | 1883 | Dane | Madison | View |
| Auld lang syne | May | 06 | 1884 | Dane | Madison | View |
| The old court house and the prospective new one | May | 06 | 1884 | Dane | Madison | View |
| A short chapter in the early history of Dane County not before published | December | 06 | 1886 | Dane | Madison | View |
| Organization of Dane county | December | 20 | 1886 | Dane | Madison | View |
| The first church in Madison | May | 22 | 1886 | Dane | Madison | View |
| The first church in Madison | May | 22 | 1886 | Dane | Madison | View |
| The new Dane county court house | November | 16 | 1886 | Dane | Madison | View |
| County of Dane - historical | January | 31 | 1887 | Dane | Madison | View |
| Pioneer County Building | June | 01 | 1888 | Dane | Madison | View |
| The official state paper fifty years old | August | 15 | 1889 | Dane | Madison | View |
| Simeon Mills made many contributions to Madison | March | 15 | 1891 | Dane | Madison | View |
| Stoner's memories: Story of early Madison told by one who arrived in 1837 | June | 06 | 1896 | Dane | Madison | View |
| Swan Lake town sites | October | 05 | 1896 | Columbia | | View |
| People with memories | March | 14 | 1897 | Dane | Madison | View |
| Stoner's memories: The story of Madison in 1837 and the years following | April | | 1897 | Dane | Madison | View |
| Early Madison | December | 03 | 1899 | Dane | Madison | View |
| Dane County in legislature | November | 06 | 1902 | Dane | Madison | View |
| Bit of History | May | 02 | 1909 | Dane | Madison | View |
| An early Madison festivity | April | 02 | 1915 | Dane | Madison | View |
| Building of state's first capitol was tedious, costly job | November | 09 | 1919 | Dane | Madison | View |
| Earliest routes into Madison | August | 03 | 1919 | Dane | Madison | View |
| Early courts of Madison | August | 17 | 1919 | Dane | Madison | View |
| Eighty-two years this very week came to Madison the first permanent settlers, Simeon Mills and A.A. Bird | June | 12 | 1919 | Dane | Madison | View |
| Early construction | March | 21 | 1922 | Dane | Madison | View |
| Madison's first social life saw existence in one room log house on bank of Monona | November | 10 | 1922 | Dane | Madison | View |
| Mills homestead | October | 06 | 1922 | Dane | Madison | View |
| Postoffice | April | 06 | 1922 | Dane | Madison | View |
| Landmark changes hands in sale of gas company office building | April | 15 | 1923 | Dane | Madison | View |
| Church clings to the square | March | 08 | 1924 | Dane | Madison | View |
| Sketch of Madison made 67 years ago shows view from present Olin Park | June | 01 | 1924 | Dane | Madison | View |
| Historic trees saved from ax | June | 16 | 1925 | Dane | Madison | View |
| Scarcity of silver caused issuance of illegal substitute | May | 25 | 1925 | Dane | Madison | View |
| First Madison hostelries offered primitive luxury | March | 20 | 1927 | Dane | Madison | View |
| Scramble for city offices as wild 80 years ago as today, old records reveal | May | 08 | 1927 | Dane | Madison | View |
| Thanksgiving originated years before early New England days | December | 02 | 1928 | Dane | Madison | View |
| Visitors pointed out first Dane courthouse for beauty | June | 10 | 1929 | Dane | Madison | View |
| Waunakee now 60 years old; Scotch family came first | December | 31 | 1929 | Dane | Waunakee | View |
| Madison Day by day | August | 02 | 1931 | Dane | Madison | View |
| Catlin's house antedated Peck's--but it burned | June | 25 | 1936 | Dane | Madison | View |
| If Col. Bird had had his way, we'd be finding our inspiration in sunsets on Lake Doty and moonlight on Lake Catlin | April | 26 | 1936 | Dane | Madison | View |
| New hotel, beautiful beyond words, opened | January | 01 | 1937 | Dane | Madison | View |
| Stagecoaches put excitement in Madison life of yesteryear | August | 02 | 1942 | Dane | Madison | View |