November 1, 1843 – Champlain & Connecticut River Railroad Company chartered
May 14, 1845 – Northern Railroad Company incorporated
November 5, 1845 – Western Vermont Railroad incorporated
1847 – Rutland & Washington chartered
November 6, 1847 – Champlain & Connecticut River Railroad changed to Rutland & Burlington Railroad Company
November 8, 1848 – Vermont Valley R.R. incorporated
November 13, 1848 – Rutland & Whitehall Railroad chartered to build a line parallel to Rutland & Washinton to Castleton
1849 – Vermont & Canada leased to Vermont Central
December 18, 1849 – First train runs over Rutland & Burlington on Bellows Falls-Burlington line
September 20, 1850 – Northern Railroad of New York opened for traffic
1851 – First refrigerator car in the U. S. placed in operation on the Northern R. R. of N. Y.
March 25, 1852 – Organization of Lebanon Springs Railroad
August 31, 1852 – Champlain Transportation Company purchased by Rutland & Burlington, service initiated to Rouses Point and Plattsburgh
November 19, 1853 – Control of Rutland & Burlington transferred to Mortgage Trustees
January 1855 – Champlain Transportation Company sold, later being purchased by Rensselaer & Saratoga
November 1, 1857 – Western Vermont R.R. leased to Troy & Boston
June 18, 1864 – Incorporation of Ogdensburg & Lake Champlain Railroad Company
May 12, 1865 – Vermont Valley R. R. leased by Rutland & Burlington
July 1865 – Through freight service provided between Rutland & Burlington and Rensselaer & Saratoga
August 1, 1865 – Formation of first Bennington & Rutland Railroad Company from Western Vermont R. R.
June 1866 – First Fenian campaign on Ogdensburg & Lake Champlain Railroad at Malone, New York
June 25, 1867 – Rutland & Burlington reorganized to form the first Rutland Railroad Company, effective July 9, 1867
November 21, 1867 – Organization of Addison Railroad Company
January 15-16, 1868 – Termination of Bennington & Rutland lease by Troy & Boston; leased by John Page & J. Gregory Smith.
1868 – John Page becomes president of the Rutland.
January 1870 – Bennington & Rutland and Lebanon Springs Railroad consolidated into Harlem Extension R. R.
March 1, 1870 – Ogdensburg & Lake Champlain leased to Vermont Central R. R.
May 26, 1870 – Second Fenian encampment at Malone, New York
September 26, 1870 – Whitehall & Plattsburgh R. R. from Ticonderoga to Port Henry leased to Rutland R.R.
December 1, 1870 – Vermont & Massachusetts leased to Rutland R.R.
December 7, 1870 – Addison Railroad leased to Rutland R.R. for 99 years
December 30, 1870 – Rutland Railroad Company leased to Vermont Central Railroad Company for 20 years from January 1, 1871
January 23, 1871 – Montreal & Plattsburgh R.R. leased to Rutland
1877 – Vermont Central R. R. terminates lease of Bennington & Rutland
1884 – Charles Clement takes over presidency of the Rutland
1888 – Percival Clement takes over presidency from his son Charles
December 31, 1890 – Rutland Railroad Company leased to Central Vermont Railway Company for 99 years from January 1, 1891, renewing the 20-year lease from the Vermont Central.
May 7, 1896 – Central Vermont in receivership; Rutland returned to owners
July 1, 1899 – Rutland-Canadian R. R. leased to Rutland R. R.
January 21, 1901 – Second Rutland Railroad Company formed by consolidation with Rutland-Canadian Railroad
September 6, 1901 – Third Rutland Railroad Company formed by consolidation with Bennington & Rutland R.R.
October 26-28, 1901 – Fourth Rutland Railroad Company formed by consolidation with Ogdensburg & Lake Champlain R. R.
December 23-24, 1901 – Fifth Rutland Railroad Company formed by consolidation with Chatham & Lebanon Valley R.R.
May 1, 1902 – W. Seward Webb assumes presidency of the Rutland
1904-05 – Controlling interest in the Rutland obtained by New York Central & Hudson River R.R.
February 1911 – Half of New York Central’s Rutland stock sold to the New York, New Haven & Hartford R.R.
July 1, 1914 – Panama Canal Act passed forcing Rutland to cease water transportation and sell shipping interests on the Great Lakes.
December 28, 1917 – Control of Rutland assumed by United States Railroad Administration
March 1, 1920 – Government control of Rutland terminated
November 3-5, 1927 – The “Great Flood” devastates the Rutland
June 25, 1932 – Passenger train service terminated on Chatham Division
May 5, 1938 – Rutland Railroad pushed into receivership
July 1938 – “Save the Rutland” club formed
January 9, 1939 – Inaugural run of The Whippet
1941 – Both New York Central and New York, New Haven & Hartford railroads sell remaining Rutland stock to private investors
November 1, 1950 – Reorganization of Rutland Railroad into Rutland Railway
May 20, 1953 – Interstate Commerce Commission approves Chatham branch abandonment
June 26, 1953 – Rutland hit by three-week strike, first strike in Rutland History. All passenger service eliminated
September 16, 1960 – Rutland hit with 41 day strike by unionized employees over changes to operating rules and division points.
November 1, 1960 – Rutland strike over.
September 25, 1961 – Rutland strike, last Rutland train operates
December 4, 1961 – Rutland applies to ICC for abandonment of entire line
March-April 1962 – ICC abandonment hearings take place, 7 days in Rutland and 2 days in Malone
September 18, 1962 – ICC approved abandonment application, effective January 29, 1963
January 28, 1963 – Railway Labor Executive Council obtains U.S. District Court injunction in Cleveland blocking abandonment
January 29, 1963 – Abandonment effective date postponed to May 20, 1963, to allow State of Vermont to secure buyers
May 29, 1963 – Vermont State Legislature passes $2.7 million funding bill allowing state to purchase certain sections of Rutland for subsequent lease to operators
November 4, 1963 – Rutland Railroad Company free to dispose of property as it sees fit- State of Vermont’s power to designate operators ends