During the American Civil War, the town again became an important river port, but by the 1890s the post office closed.

The community is located on the west side of Bear Creek where it flows into the Tennessee River.

Steamboats plying the Tennessee River docked there to bring goods in and out of northern Mississippi.

The town's population may have reached 2,000 with a post office, many businesses, Baptist and Methodist churches, a Masonic lodge, a hotel, and a girls school.

The turning point came in 1857 when the town's leaders rejected an offer to run the Memphis and Charleston Railroad through Eastport.