1891 - Bolivar Race Track Association organized; C.M. Mix Pres. New Masonic Temple dedicated. $22,000 fire at Ceres destroys Hotel, Opera House, Printing Plant, Drug Store, General Store, and four residences.
1892 - Bolivar's Bowery, Railroad Street raided by Police in Vice Raid. New Race Track opened; 800 seat Grandstand. Thomas Erwin blown up in glycerin explosion at McDonald, Pa.
1893 - Cyclone strikes oil field destroying 500 rigs; $20,000 damage. Frank E. Gannett one of 9 members of graduating class of Bolivar academy. Gannett later founded the famous Gannett Publishing Chain. M.F. Van Curen blown up in glycerin explosion near Pittsburgh, Pa. A daily stage route established between Bolivar and Wellsville.
1894 - Floods cause heavy damage in county in May. Eastern Star organized.
1895 - Wilson Machine Shop destroyed by fire; $4,000 damage. New Allegany Jail opened in Belmont.
Manchester house and Mead's Mill destroyed by fire. Bolivar Water system is completed. Drum building burns. Central New York and Western Railroad widened to standard size. Bolivar celebrates Centennial of its founding. Grand Central Hotel and 7 other buildings in Ceres destroyed by fire; $20,000 damage.
Over 7,000 wells completed in Allegany field during the year.
1896 - P.H. Dougherty owner of Pierce Roadster. Record to Olean 18 miles in one hour, 7 minutes by Victor Hammond's car.
1897 - P.H. Dougherty signs to play professional ball. Henry H. Young blown up in glycerin explosion.
1898 - Bolivar Free Library opened March 24th.
1899 - The Pittsburg, Shawmut and Northern Railroad organized.
1900 - Ed Wilson buys first Loco-mobile in Bolivar. Heavy windstorm damages many oil derricks.
1901 - Famous Opera House fire wipes out 3 buildings in $20,000 fire. Fielder A. Jones joins Chicago American League team. Shawmut broad-gauge between Bolivar and Olean.
1902 - Rural Free Mail established. Flood does $60,000 damage in county. Voting machines purchased by Village Board.
1903 - Street signs erected.
1904 - Coldest day recorded; 37 degrees below zero. William Adams blown up in explosion.
U.S. Express opens office. New Catholic brick and stone church built. Bolivar builds new $25,000 school building.
1905 - Worker on new High School building shot and killed by fellow worker.
Saint Mary's Church dedicated.
1906 - Central Iron Works destroyed by fire.
Crandall block wrecked by fire. Odd Fellows Temple erected.
J .H. Reynolds takes possession of first concrete house in Bolivar on Wellsville Street.
1912 - Fire in Bartlett and Hills General Store in Allentown.
1913 - New jail on First Street in Bolivar. Burdick store and Post Office destroyed by fire in Little Genesee. Van Curen Glycerin Factory blown to bits.
1921 - St. Mary's Hall sold to Seventh Day Adventists. Matson building damaged by fire.
1922 - Village Hall completed at Main and Olean Streets.
1923 - Electric current turned on in streets of Bolivar. Allentown and Bolivar concrete road built. New water lines laid. Firemen buy new truck and install electric fire alarm system.
1925 - Bolivar Post Office raised to second class status. Bolivar-Wellsville Highway opened. Modern Telephone System installed.
1926 - Parent-Teachers Association formed. Flagpole raised by American Legion on the Library lawn. Olean-Bolivar trolley line dismantled.
1958 - Governor Harriman visits Bolivar.
1959 - Flood on First and Leather Streets.
1960 - Bowl-O-Var Bowling Alley opened.
1961 - Parking meters removed. February low temperature 26 degrees below zero.