Once inside the city, the route turns north at MS 15 and travels through downtown Pontotoc.

The road enters Okolona west of CR 139,[4] and passes through a residential area within the city as East Monroe Avenue.

[8] The route continues traveling through farmland, intersecting CR 137 and smaller driveways.

Southeast of CR 243, MS 41 enters the northeastern edge of the Tombigbee National Forest.

[5] MS 41 continues northwestwards and intersects CR 97 in Troy, which leads to Woodland.

[5] The route enters the city of Pontotoc east of Country Village Lane, and it turns north at MS 15.

Past Tenth Street, the road crosses over the Mile Branch.

[7] The road that became part of MS 41 first existed as an Indian trail, later used by both belligerents in the Civil War.

[14][15] Around 1936, the section of MS 41 from Okolona to US 45 was rerouted southwards, creating a one mile (1.6 km) concurrency at US 45.