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The Rutland Railway (reporting mark R) was a small railroad in the northeastern United States, primarily in the state of Vermont but extending into the state of New York. The earliest ancestor of the Rutland, the Rutland & Burlington Railroad, was chartered in 1843 by the state of Vermont to build between Rutland and Burlington. A number of other railroads were formed in the region, and by 1867 the Rutland & Burlington Railroad had changed its name to simply the Rutland Railroad.

Between 1871 and 1896 the Rutland Railroad was leased to the Central Vermont, regaining its independence when that road entered receivership. The New York Central Railroad briefly had a controlling interest in the Rutland from 1904, but sold half of its shares to the New York, New Haven & Hartford Railroad in 1911.

The Rutland's primary freight traffic was derived from dairy products and to many[by whom?] the railroad is fondly remembered by the long trains of milk that used to move over the system. At its peak the Rutland served about a 400-mile (600w km) system that roughly resembled an upside-down L running from Chatham, New York north to Alburgh, Vermont (the railroad's furthest northern terminus was Noyan, Quebec) and then west to Ogdensburg, New York along the St. Lawrence River. Never a solid financial operation, the Rutland entered receivership for the first time in 1938. Cost cutting, including wage reduction, brought things around. A reorganization in 1950 changed the name from Rutland Railroad to Rutland Railway.

In 1961, after further strikes, the railroad apparently decided it was no longer viable, and applied to the Interstate Commerce Commission for complete abandonment. This was approved, and the railroad closed down on May 20, 1963. The strike was brought on by the employees' unwillingness to accept operational changes that would have moved the center of Rutland operations from Rutland to Burlington. This would have required them to relocate from Rutland to Burlington.