[2] During the Revolutionary War there were a number of forts and roads that went through the area now known as Rutland County.

[3] The Crown Point Road (which was built in 1759 and used until 1783) goes through the modern day towns of Whiting, Sudbury, Hubbardton, Castleton, Ira, Rutland, Clarendon, Shrewsbury, Wallingford and Mount Holly and extended all the way to Fort at Number 4, Charlestown, New Hampshire.

[27] On April 7, 1880, the county lost to Washington County, New York, when New York gained a small area west of the village of Fair Haven from Vermont due to a change in the course of the Poultney River, a change too small to see on most maps.

[40] In 1828, Rutland County was won by National Republican Party candidate John Quincy Adams and by Henry Clay in 1832.

From William Henry Harrison in 1836 to Winfield Scott in 1852, the county would be won by Whig Party candidates.

From John C. Frémont in 1856 to Richard Nixon in 1960, the Republican Party would have a 104-year winning streak in the county.

In 1964, Rutland County was won by Democratic Party incumbent President Lyndon B. Johnson, who became the first Democratic presidential candidate to not only win the county, but to win the state of Vermont entirely.

Following the Democrats' victory in 1964, the county went back to voting for Republican candidates for another 20 year winning streak starting with Richard Nixon in 1968 and ending with George H. W. Bush in 1988, who became the last Republican presidential candidate to win the county.

Republicans see greater success at a local level in Rutland County.

In nine of the ten past gubernatorial elections, the Republican candidate has won the greatest number of votes in Rutland County.

Most recently, incumbent Republican governor Phil Scott won 80 percent of Rutland County's votes in the 2024 Vermont gubernatorial election.

The Rutland–Southern Vermont Regional Airport is located just south of Rutland city in North Clarendon.

Passenger rail service is provided by Amtrak via the Ethan Allen Express which connects Rutland with Burlington and New York City.

Premier Coach's Vermont Translines serves Rutland daily with two intercity bus connections between Burlington, Lebanon, New Hampshire and Albany, New York in a partnership with Greyhound.