| 1592 to 1755 | Peak of Spanish interest and exploration on Pacific Northwest coast. |
| 1728 to 1768 | Peak of Russian exploration on Northwest coast. |
| 1778 | Captain James Cooke reported a river at the position of the Umpqua. |
| 1820 to 1821 | “Old Establishment” or “McKay’s Fort” - fur post for Northwest Company. |
| 1826 | David Douglas travels through Willamette and Umpqua Valleys on botanical expedition with Hudson Bay Company. |
| July 1828 | Expedition from Sacramento Valley to Fort Vancouver led by Jedediah S. Smith massacred at mouth of Smith River. |
| 1828 | Fort Vancouver trappers explore Umpqua country. |
| 1836 | Fort Umpqua, Hudson Bay Company fur post, established at Elkton with Jean Baptiste Gagnier as manager. |
| 1837 | Ewing Young passes through Umpqua Valley with cattle from California. |
| July 1843 | Provisional government of Oregon meeting at Champoeg divides Oregon into four administrative districts. The Southwestern district including western Umpqua Valley was called the Yamhill District and the Southeastern District including eastern Umpqua Valley was called the Champooick District. |
| 1844 | Jesse Applegate appointed Surveyor General of Oregon. |
| July 1845 | Provisional government of Oregon elects George Abernethy first governor of Oregon. |
| December 1845 | Western Umpqua Valley part of Polk County. Eastern Umpqua Valley part of Champoeg County. |
| June 1846 | Lindsay and Jesse Applegate and Levi and John Scott lead wagon train over “Applegate Trail” (or Southern Route) from Fort Hall to Willamette Valley through Umpqua Valley. |
| 1846 | Major Thorp, Job Hatfield, William Golden, Rufus Butler and party explore Umpqua Valley. |
| 1847 | Drain settled by Warren Goodell. |
| December 1847 | Western Umpqua valley part of Benton County - County seat, Marysville (Corvallis); eastern Umpqua Valley part of Linn County - County seat, Albany. |
| August 1848 | General Joseph Lane appointed first Governor of the Oregon Territory by President Polk. Term of office, 1848-1850. |
| 1849 | Jesse Applegate and family settled at Yoncalla. |
| June 1850 | Winchester Payne and Company of San Francisco expedition, on board the “Samuel Roberts,” founded towns of Scottsburg, Winchester, Umpqua City and Elkton. Scottsburg built as outfitting point for the mines of northern California and southern Oregon. |
| April 1851 | William H. Riddle settles at Cornutt near Riddle. |
| June 1851 | Joseph Lane elected Representative to Congress from Oregon Territory. Term of Office 1851 to 1859. |
| Sept 1851 | Aaron Rose settles at Deer Creek. |
| 1851 | Joseph Knott, second settler at Canyonville, opens store. |
| Jan 1852 | Douglas and Jackson Counties created out of Umpqua County. Douglas County included that portion of the present County south of the north Umpqua River with County seat at Winchester. Jackson County included the present Jackson, Josephine, and Curry Counties with County seat at Jacksonville. Douglas County was named for Senator Stephen A. Douglas of Illinois. |
| July 1852 | Umpqua County seat at Elkton. |
| 1852 | Abraham Patterson and William P. Day first settlers in Camas Valley. |
| October 1853 | First public school in County organized at Garden Valley. |
| December 1853 | Coos County created out of portions of Umpqua and Jackson Counties. Included present Coos and Curry Counties with County seat at Empire City. |
| March 1854 | Rev. James H. Wilbur founds the first secondary school - The Umpqua Academy at Wilbur. |
| 1855 | Deer Creek name changed to Roseburg. |
| October 1855 | Rogue River Indian Wars began. |
| 1856 | Rogue River Indian Wars end and Indians moved to Siletz and Grand Ronde Indian Reservations. |
| 1856 | U.S. Army builds Fort Umpqua at mouth of Umpqua River. |
| Dec 1856 | Camas Valley annexed to Douglas County from Coos County. |
| 1857 | Umpqua Lighthouse constructed (destroyed in 1861). |
| 1858 | Colonel (later “General Fighting Joe”) Hooker builds Hooker Road from Scottsburg to Camp Stewart. |
| February 1859 | Umpqua County seat moved to Green Valley. |
| July 1860 | The first “California-Oregon” stage run. |
| December 1861 | Great flood destroys Scottsburg. |
| August 1861 [sic] | Umpqua County seat moved to Yoncalla. |
| September1862 | Addison C. Gibbs, early settler at Gardiner, elected Governor of Oregon. Term of office, 1862-1866. |
| October 1862 | Umpqua and Douglas Counties merged to form the present Douglas County. |
| 1862 | School District Number 1 formed at Oakland. |
| 1863 | Telegraph service reaches County. |
| October 1862 [sic] | Voters fail to approve re-division of Douglas County. Umpqua County seat would have been Oakland. Douglas County could have chosen Canyonville, Myrtle Creek, Round Prairie or Roseburg. |
| 1870 | Steamboat “Swan” reaches Roseburg. |
| October 1870 | City of Roseburg incorporated. |
| 1872 | Ben Holladay’s Oregon and California Railroad reaches the County. |
| 1872 | Moved to New Site (Oakland). |
| 1873 | Coos Bay Military Road built from Coos Bay to Roseburg. |
| 1873 | Coos Bay, Roseburg, and Eastern Railroad started at Marshfield. (Never reached beyond Myrtle Point.) |
| 1874 | Ben Holliday and Henry Villard meet at Roseburg. |
| September 1877 | Stephen F. Chadwich of Roseburg, Secretary of State, September 1870 to September 1877 - Governor of Oregon, September 1877 to September 1878. |
| October 1878 | City of Oakland incorporated. |
| September 1880 | President Rutherford B. Hayes, General William Tecumseh Sherman, and Secretary of War Ramsey tour County. Stayed overnight in Roseburg. |
| August 1882 | Last “California-Oregon” stage run from Oregon. |
| October 1882 | County lines established. |
| 1882 | Nes Odessa, Russian Jewish colony, founded at Glendale. |
| 1893 | City of Riddle incorporated. |
| 1893 | Drain Normal School opened. (Closed 1907.) |
| May 1894 | Oregon Soldier’s Home dedicated at Roseburg. |
| 1895 to 1930 | Great prune era of Douglas County. |
| February 1901 | City of Yoncalla incorporated. |
| 1901 | City of Canyonville incorporated. |
| 1901 | City of Glendale incorporated. |
| 1901 | City of Myrtle Creek incorporated. |
| August 1905 | Oregon Western Railway Company was incorporated - to build from Drain to Reedsport. (Project was abandoned 1914.) |
| 1907 | City of Drain incorporated. |
| 1909 | Sisters of Mercy established Mercy Hospital. |
| 1911 | City of Sutherlin incorporated. |
| 1913 | Port of Umpqua Commission founded. |
| April 1916 | Willamette Pacific Railroad opens Reedsport and Coos Bay to rail service to Eugene. |
| 1917 | North Jetty on Umpqua River constructed by Corps of Engineers. |
| 1919 | City of Reedsport incorporated. |
| June 1919 | Roosevelt Coast Military Highway authorized by Congress. |
| 1925 | Canyonville Bible Academy founded. |
| 1928 | Southern Pacific Railroad division moved from Roseburg to Eugene. |
| 1932 | Veterans Administration Hospital started at Roseburg. |
| 1948 | City of Elkton incorporated. |
| September 1953 | City of Winston incorporated. |
| September 1954 | Only nickel refinery in nation starts production at Riddle. |
| August 1959 | City of Roseburg partially destroyed in blast and fire. |
| October 1962 | Columbus Day Storm’s hurricane winds destroyed property throughout Douglas County. |
| December 1964 | Great Christmas flood. |
| November 1966 | Interstate-5 Highway completed. |
| December 1967 | Umpqua Community College dedicated. |
| March 1998 | Glenbrook Nickel Mine closure. |