| 1882 | Crook County first created out of southern
part of Wasco County. Contained 8,600 square miles and had a population of 2,500. |
| 1882 | Governor appointed first county officers, County Court held first court session |
| 1884 | Prineville Volunteer Fire Department organized |
| 1886 | First Crook County Courthouse built - cost $5,474.00 |
| 1887 | First Bank |
| 1890 | Electricity came to Prineville |
| 1899 | First telephone service |
| 1902 | First Crook County Fair |
| 1903 | Smallpox epidemic |
| 1905 | First high school opens |
| 1909 | First theater Stone courthouse completed |
| 1914 | Jefferson county created from Crook County |
| 1916 | Deschutes County created from Crook County |
| 1917 | City of Prineville Railway construction began |
| 1920 | Ochoco Dam project completed |
| 1922 | Prineville fire - 20 businesses destroyed |
| 1930 | Lumber industry flourished between 1930 and
1940 and Prineville became nation's largest shipping point of pine lumber |
| 1932 | Gymnasium on Fairview Street built with donated
money and labor...a community project |
| 1934 | Prineville Airport dedicated |
| 1935 | New Crook County High School opens with 135 enrollments |
| 1938 | Crooked River Grade School built at 1st and
Fairview Streets Iron Railing added to Courthouse entrance steps |
| 1940 | First dial telephones |
| 1941 | Courthouse remodeled...east and west step and entrances removed |
| 1945 | First Crooked River Roundup |
| 1947 | Ochoco Elementary School built |
| 1949 | First Lord's Acre Sale (Powell Butte) |
| 1951 | Les Schwab opened first tire store |
| 1952 | Worst flood in previous 50 years |
| 1953 | New Crook County High School built on Knowledge Street |
| 1959 | New Junior High built on SE Second Street extension |
| 1960 | First Crook County Rockhound Pow-Wow |
| 1962 | Crooked River Project, A.R. Bowman Dam dedicated |
| 1963 | Funds approved for new Post Office building,
to be located on Court St. U.S. Bank opens |
| 1966 | Ochoco Inn burned |
| 1971 | First Timber Carnival |
| 1982 | Hudspeth Sawmill closes |
| 1984 | Crook County Cowboys State Football Champs |
| 1988 | Crook County only Bellwether county in nation...has
picked winner since 1882 Highway 26 added to "Access Oregon" |
| 1989 | Courthouse closure due to structural deterioration on 12/19/1989 |
| 1990 | Courthouse repaired and reopened |
| 1992 | Pine Products Sawmill closure |
| 1993 | Oregon Trail Sesquicentennial Celebration |
| 1994 | Crook County looses Bellwether status Ochoco Dam reclamation project begins |
| 1995 | Re-do Ochoco Dam reclamation project |
| 1996 | New Crook County High School built on Lynn
Blvd. Former high school becomes
Crook County Middle School; former middle school becomes Cecil Sly Elementary School Hot Shot Memorial dedication in Ochoco Creek Park |
| 1998 | Ochoco Dam and Ochoco Creek flood damaged
over 400 homes and was declared a national
disaster by President Clinton. |
| 1999 | New Library opened at Meadow Lakes Drive |
| 2000 | Hash Rock Fire |
| 2001 | BiMart Opened |
| 2002 | Prineville gets 5th stop light at corner of Hwy 26 and Combs Flat Road |