| 1676 | "Naval Battle" on Lake Waushacum between Colonists and Indians. |
| 1701 | Purchase of Additional Grant (Chocksett) from George Tahanto, Sholan's nephew. |
| 1707 | Last Indian Fight (Rowley Hill). |
| 1720 | First five settlers from Lancaster—Gamaliel Beaman, Benjamin Houghton, Samuel Sawyer, David & Jonathan Osgood. |
| 1730-40 | Influx of settlers from Lancaster, Rowley,Woburn, and other coastal towns. |
| 1733 | First petition for a separate town. |
| 1734 | Jonas Houghton laid out the first road from and along the north side of Mt. Wachusett. |
| 1736 | Old cemetery established.Lancaster through the "additional grant". |
| 1742 | Setting off of the "Second Precinct" from Lancaster. |
| 1743 | First schoolhouse built in the Center. |
| 1744 | Meeting-house completed and Rev. John Mellen ordained. |
| 1755-60 | French and Indian Wars. |
| 1755 | "Great Earthquake." |
| 1756 | Year of the great sickness, attributed to the earthquake. Many children died. Other epidemics in 1786 and 1796. |
| 1759 | First dwelling built in the Center by Jabez Brooks. |
| 1774 | Rev. Mellen dismissed. Militia organized. |
| 1779 | Rev. Reuben Holcomb ordained as the second minister. |
| 1776-82 | Revolutionary War. |
| 1781 | West (second) Precinct incorporated as a separate town named Sterling, April 25. |
| 1790 | First census reports 209 dwellings and 1428 inhabitants in the Town. |
| 1793 | Robert B. Thomas started his Old Farmer's Almanac. Still published! |
| 1794 | Town records burned. |
| 1797 | Town redistricted and eight new schoolhouses built. Now each district had a schoolhouse: Chocksett, Cookshire, Justice Hill, Leg, Upper & Lower North Row, Redstone, River, Rowley Hill, and Squareshire, plus the Center. |
| 1799 | Second Meeting-house built. |
| 1800 | First Town House built with schoolroom on upper floor for village children. |
| 1804 | First "Social Library"—a voluntary association. |
| 1808 | Part of Leg District set off to West Boylston. |
| 1814 | Mary's Little Lamb followed her to school. |
| 1822 | Sterling Light Infantry organized. |
| 1824 | Lafayette's visit. |
| 1826 | Sterling Guards organized. |
| 1830 | Central Hotel built on site of Brooks' Tavern. |
| 1835 | New Town Hall erected—the present one. New brick schoolhouse on School Street. Last class there 1957. Now the American Legion Post headquarters. |
| 1837 | Bartlett's Store established and carried on for almost 100 years. |
| 1838 | Universalist Church built, corner of Main and Maple Streets. Sold in 1853 to the First Evangelical Congregational Society. Last used for church services in the 1940's. |
| 1842 | Fire destroyed the Meeting-house. Third one built on same site. Now the First Church in Sterling. |
| 1843 | Baptist Church built. Razed 1924. Now site of Butterick School. |
| 1848 | First train through Sterling Junction, Worcester & Nashua R.R. |
| 1849 | First train through Sterling Center, Fitchburg to Sterling Junction. |
| 1850 | First passenger train passed through town. |
| 1852 | Allendale School, a private boarding school for boys, established. Closed 1864. First Meeting of the Methodist at the Camp Ground, Sterling Junction. |
| 1857 | Beginning of the Farmers' Club. Association |
| 1859 | First Cattle Show—held annually on the Common for 100 years, except during war time. |
| 1861 | Civil War-178 Sterling men involved. -65 Sterling Home Guard unit active. |
| 1863 | Ebenezer Butterick cut his first paper shirt pattern, the beginning of the Butterick Pattern & Publishing Company. |
| 1866 | Civil War monument erected on the Common. |
| 1868 | Major James A. Pratt GAR Post 59 organized. |
| 1871 | Free Public Library established. Two rooms over the Bartlett Store. |
| 1874 | Sterling Grange organized. |
| 1879 | Waushacum Park established at West Lake. Fire Department Engine Company formed. |
| 1881 | CENTENNIAL ANNIVERSARY OF INCORPORATION. |
| 1883 | High School built. Last graduating class 1916. Used as elementary school until 1934. Now Electric Light Dept. |
| 1885 | Library building erected, gift of Edwin A. Conant. |
| 1890 | Central Hotel burned. Rebuilt as "Conant Hotel" on same site. |
| 1895 | Wachusett Reservoir constructed absorbing some 1400 acres of Sterling for the reservoir and watershed areas. |
| 1896 | Present Town Seal adopted. |
| 1901 | First Rural Free Delivery of mail (from Pratt's Junction). |
| 1903 | Hotel, now named the "Sterling Inn" burned again. Reestablished at present site, then the home of Moses Heywood. First telephone switchboard in town at the Tenney home on Maple Street. |
| 1906 | First electric car (trolley) through town, Worcester to Leominster. |
| 1908 | Present Sterling Inn constructed. |
| 1911 | First electric lights in town. |
| 1913 | First Parcel Post service. |
| 1914 | Baptist & Congregational Churches joined. supplying water to Boston. |
| 1916 | Last class graduated from Sterling High School. Wausham Park abolished as West Lake becomes part of the MDC system |
| 1917-18 | First World War-68 Sterling men involved. |
| 1917 | Home Guards formed, later mustered into MSG 19th Regt., Co. D. |
| 1919 | Hiram 0. Taylor American Legion Post 189 organized. Ladies' Auxiliary formed 1922. |
| 1920 | Tax list shows 104 Sterling residents now own automobiles! Big Blizzard! Snow removal bills $6,000. |
| 1921 | Boy Scouts organized. |
| 1923 | Girl Scouts organized. |
| 1924 | Baptist Church razed. |
| 1926 | Last passenger train through Sterling Center. First bus through town. |
| 1927 | Last trolley run. |
| 1930 | Public water supply established for the eastern section of town. |
| 1931 | SESQUICENTENNIAL CELEBRATION. |
| 1934 | Sholan Park established at East Lake Waushacum, gift of Howard E. Hall. |
| 1935 | Butterick School built on land donated by Mary Ellen Butterick. |
| 1936 | Chocksett Club organized. |
| 1938 | Destructive hurricane. Others which caused damage, in 1945, 1954, 1955. |
| 1941-45 | Second World War. |
| 1943 | Woman's Club organized. |
| 1943-45 | Sterling Bugle printed—a newsletter for servicemen and women. |
| 1946 | Airport established on the old Negro Bros. farm on Greenland Road. |
| 1949 | Unitarian & Federated Churches merged. |
| 1950-58 | Korean War. |
| 1953 | Sportsmen's Club started developing property on Beaman Road. |
| 1954 | St. Richard's of Chichester, new Catholic Church dedicated. Wachusett Regional High School opened. |
| 1955 | Farm lands begin disappearing into housing developments. |
| 1956 | Dial telephone service installed. Volunteer Ambulance Service started by firemen. |
| 1957 | Dedication of War Memorial to World War I and II and Korean veterans. West Sterling P.O. closed. Florence G. Houghton Elementary School built. Additions 1962 and 1971. |
| 1958 | New fire station. |
| 1963 | Sterling Historical Society founded. Headquarters on Pine Street purchased 1968. |
| 1964-73 | Vietnam Conflict. |
| 1971 | New Baptist Chapel established. |
| 1976 | Seventh-Day Adventist Church erected. |
| 1977 | Construction begun on new north-south interstate highway, 1-190. |
| 1978 | Blizzard, February 6-9. |
| 1979 | New Chocksett School opened. |
| 1980 | Population 5,610. |
| 1981 | BICENTENNIAL ANNIVERSARY OF INCORPORATION. |
