The Milton-Madison Bridge (also known as the Harrison Street Bridge) is a continuous truss bridge that connects Milton, Kentucky and Madison, Indiana.

It connects Maysville, Kentucky and Aberdeen, Ohio.

The other is the Cumberland Gap Tunnel, connecting Tennessee and Kentucky.

John F. Kennedy Memorial Bridge across the Ohio River, connecting Louisville, Kentucky and Jeffersonville, Indiana.

The bridge carries U.S. Route 27 across the Ohio River, connecting Newport, Kentucky and Cincinnati, Ohio.

Years later, stage coaches began to connect eastern Kentucky and Johnson County to the bluegrass region and the rest of civilization.

There is a bridge across the Ohio River at Brookport, that connects Kentucky and Illinois.

It is 1395 feet (425.2 m) long, and connects Gallatin County, Kentucky, and Switzerland County, Indiana.

The North-South Michigan Road was built in the 1830s, connecting Michigan and Kentucky and passing through Indianapolis in the middle.

Two steel-girder bridges were completed over the Big Sandy River connecting Kentucky to West Virginia.