Statewide transportation developed slowly in Kentucky. Although freight and passengers were carried by river and later by rail during the 19th century, mountains and lack of good roads made land travel in eastern Kentucky so arduous that the region was for a long time effectively isolated from the rest of the state.
The first railroad in Kentucky, the Lexington and Ohio, opened on 15 August 1832 with a 26-mi (42-km) route from Lexington to Frankfort. Not until 1851 did the railroad reach the Ohio River. In November 1859, Louisville was connected with Nashville, Tennessee, by the Louisville and Nashville Railroad; heavily used by the Union, it was well maintained during the Civil War. Railroad construction increased greatly after the conflict ended. By 1900, Kentucky had three times the track mileage it had had in 1870. As of 2000, Kentucky had 2,962 rail mi (4,766 km), of which about 80% was Class I track. Also in 2000, there were five Class I railroads operating in the state. In the same year, 86% of the rail tonnage originating within Kentucky was coal. Rail service to the state, nearly all of which was freight, was provided by 16 railroads. There are four Amtrak stations in Kentucky.
The trails of Indians and buffalo became the first roads in Kentucky. Throughout the 19th century, counties called on their citizens to maintain some roads although maintenance was haphazard. The best roads were the toll roads. This system came to an end as a result of the "tollgate war" of the late 19th and early 20th centuries—a rebellion in which masked Kentuckians, demanding free roads, raided tollgates and assaulted their keepers. Not until 1909, however, was a constitutional prohibition against the spending of state funds on highways abolished. In 1912, a state highway commission was created, and by 1920, roads had improved considerably. In 2000, Kentucky had 79,267 mi (127,567 km) of public roads and 2,694,469 licensed drivers. In the same year, 1,673,926 automobiles, 1,139,543 trucks, and 12,934 buses were registered in the state.
Until displaced by the railroads in the late 1800s, the Ohio River and its tributaries, along with the Mississippi, were Kentucky's primary commercial routes for trade with the South and the West. The Kentucky Port and River Development Commission was created by the legislature in 1966 to promote river transportation. Louisville, on the Ohio River, is the chief port. In 2000, traffic through the port totaled 8.8 million tons, up from a 1982 low of only 5.7 million tons. Paducah is the outlet port for traffic on the Tennessee River.
In 2002 there were 141 airports and 57 heliports in Kentucky. The largest of these is Cincinnati/Northern Kentucky International Airport, with 11,223,966 people enplaned in 2000.