| Headline | Month | Day | Year | County | City |
|---|
| A little light on the 'silver' bearing rocks of the south shore of Lake Superior | | | No Year | Ashland | Ashland | View |
| Executed by spaniards | | | No Year | Ashland | Ashland | View |
| Ohio man pays tribute to pioneer known as Johnny Appleseed | | | No Year | Ashland | Ashland | View |
| Ashland! | January | 04 | 1873 | Ashland | Ashland | View |
| Who first mined copper on Lake Superior | January | 25 | 1873 | Ashland | Ashland | View |
| The early missions of the great lakes | April | 17 | 1874 | Ashland | Ashland | View |
| A-go-ge-bic | February | 09 | 1884 | Ashland | Ashland | View |
| An ideal resort | | | 1895 | Ashland | Ashland | View |
| Beautiful isles of chequamegon | December | 21 | 1895 | Ashland | Apostle Islands | View |
| Proposed state of superior | May | 05 | 1895 | Ashland | | View |
| The mortgage is destroyed by fire | January | 24 | 1900 | Ashland | Ashland | View |
| Passing of a historic character | February | | 1901 | Ashland | Ashland | View |
| Spooner pleads for harmony | October | 29 | 1902 | Ashland | Ashland | View |
| The planting of the cross | February | 26 | 1902 | Ashland | Ashland | View |
| When did Jefferson Davis administer to Abraham Lincoln the oath of Allegiance to the United States? | June | | 1902 | Ashland | Ashland | View |
| Reminescences of a third of a century | September | 10 | 1904 | Ashland | Ashland | View |
| Old Ashland | February | 19 | 1906 | Ashland | Ashland | View |
| A bit of history | May | 16 | 1908 | Ashland | Ashland | View |
| Algonquin era | February | 07 | 1908 | Ashland | Ashland | View |
| First court house | July | 03 | 1908 | Ashland | | View |
| 70 years tomorrow | June | 26 | 1909 | Ashland | Ashland | View |
| Forty-two years ago | July | 01 | 1909 | Ashland | Ashland | View |
| Early history of ashland | May | 03 | 1910 | Ashland | Ashland | View |
| Historic Storms | September | 13 | 1911 | Ashland | Ashland | View |
| To have big fair in fall | April | 25 | 1913 | Ashland | Ashland | View |
| Historic old church is restored | August | 11 | 1915 | Ashland | | View |
| Ashland over 40 years ago | January | 27 | 1916 | Ashland | Ashland | View |
| Ashland's future viewed from the past | March | 18 | 1916 | Ashland | Ashland | View |
| Henry Bitschenauer traces two treaties | January | 15 | 1916 | Ashland | Ashland | View |
| Old Indian granted pension at last | October | 16 | 1916 | Ashland | Ashland | View |
| Reminiscences of Father Verwyst | October | 23 | 1916 | Ashland | Ashland | View |
| The Apostle Islands are discovered | May | 08 | 1916 | Ashland | Apostle Islands | View |
| Old Treaty Hall changes hands | August | 03 | 1917 | Ashland | | View |
| Ashland as it was 55 years ago | August | 28 | 1920 | Ashland | Ashland | View |
| Indian lands being sold | August | 06 | 1920 | Ashland | Ashland | View |
| Upper Wisconsin in history and romance - no. XI. The ancient home of the Ojibways | November | 26 | 1920 | Ashland | | View |
| 85 year old chief still leads dance | August | 21 | 1921 | Ashland | Ashland | View |
| Hill celebrates 60th anniversary | September | 06 | 1921 | Ashland | Ashland | View |
| Historical data a little movie | November | 02 | 1921 | Ashland | Ashland | View |
| New "Boost Wisconsin" organization formed | August | 25 | 1921 | Ashland | Ashland | View |
| Squaw Bay caves have no rival | August | 23 | 1921 | Ashland | Big Squaw Bay | View |
| An old Ashland County newspaper found | March | 31 | 1922 | Ashland | Butternut | View |
| Drug store fifty years old | August | 10 | 1922 | Ashland | Ashland | View |
| Madeline Island is treasure spot of romantic interest: Apostle group figures in Wisconsin's early history | August | 13 | 1922 | Ashland | | View |
| Old landmark torn down | September | 15 | 1922 | Ashland | Ashland | View |
| Apostle Islands located off Bayfield Peninsula, sublime in insolation, sandy shores | October | 07 | 1923 | Ashland | Apostle Islands | View |
| Ashland vibrant with old legends | July | 25 | 1923 | Ashland | Ashland | View |
| Historic tomkins railroad, once an election issue, now a landmark | April | 06 | 1923 | Ashland | Ashland | View |
| Island pioneer missionary's son | February | 16 | 1923 | Ashland | Ashland | View |
| Landmark of Ashland burns | July | 06 | 1923 | Ashland | Ashland | View |