| Headline | Month | Day | Year | County | City |
|---|
| Early Incidents and Anecdotes | | | No Year | Waukesha | Oconomowoc | View |
| Plan season of drama in Coach House | | | No Year | Waukesha | Oconomowoc | View |
| Sherman Booth arrives in Oconomowoc | August | 12 | 1884 | Waukesha | Oconomowoc | View |
| His eightieth anniversary | October | 16 | 1897 | Waukesha | Oconomowoc | View |
| Edwin Hurlbut of Oconomowoc claims to be the founder of the Republican Party | September | 14 | 1903 | Waukesha | Oconomowoc | View |
| The Fortnightly Club | May | 09 | 1903 | Waukesha | Oconomowoc | View |
| Early days in Oconomowoc | October | 29 | 1904 | Waukesha | Oconomowoc | View |
| Survey of the Milwaukee and Rock River Canal in Waukesha County | November | 12 | 1904 | Waukesha | Oconomowoc Lake | View |
| Old settlers' meet | July | 07 | 1905 | Waukesha | Oconomowoc | View |
| Old settlers picnic a brilliant assembly | August | 04 | 1906 | Waukesha | Oconomowoc | View |
| The assembly of the old settlers | August | 11 | 1906 | Waukesha | Oconomowoc | View |
| Eighty odd years ago | July | 09 | 1915 | Waukesha | Oconomowoc | View |
| The city of lakes | March | 26 | 1915 | Waukesha | Oconomowoc | View |
| Law partner of Daniel Webster | December | 01 | 1916 | Waukesha | Oconomowoc | View |
| Few waited for the draft in 1861-1865 | May | 11 | 1917 | Waukesha | Oconomowoc | View |
| Recalling other days | March | 30 | 1917 | Waukesha | Oconomowoc | View |
| Oconomowoc the beautiful; peerless city by the lakes | January | 07 | 1920 | Waukesha | Oconomowoc | View |
| In the early days | January | 28 | 1921 | Waukesha | Oconomowoc | View |
| Famous resort fades in ruins | May | 21 | 1922 | Waukesha | Oconomowoc | View |
| "History of Oconomowoc" wins second place in county contest | August | 02 | 1924 | Waukesha | Oconomowoc | View |
| Historic hotel ruined by fire | April | 04 | 1927 | Waukesha | Oconomowoc | View |
| Early history of Oconomowoc | October | 10 | 1935 | Waukesha | Oconomowoc | View |
| May Woodruff describes early days among oconomowoc's first settlers | October | 10 | 1935 | Waukesha | Oconomowoc | View |
| Oconomowoc Lake Club dinner for founders | August | 02 | 1942 | Waukesha | Oconomowoc Lake | View |
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