It sits in the valley of Maeystown Creek, which flows into the floodplain of the Mississippi River 2 miles (3 km) to the southwest.

He subsequently left the Illinois Territory for Tennessee, where he married Mary Fletcher-Harris, and returned in 1797, adding another 100 acres (0.40 km2) to his holdings.

Maeystown may be said to have begun its growth as a town in the year 1852, when Jacob Maeys built a sawmill on what had become known as McRoberts Meadow, which he purchased in 1848.

For a year after its construction the mill remained idle, on account of there not being sufficient water to drive it.

The first store was opened in 1858 by Jacob Maeys in partnership with Judge Abraham Poston.

A post office was established in 1860, which changed the name to Maeystown, with Jacob Maeys appointed as first postmaster.