SR 56 continues northward to the Crow Creek Valley, which is full of farmland, and passes through Sherwood before the highway becomes very curvy as it ascends into the Cumberland Plateau, passing through the Sherwood Forest, Carter State Natural Area, and Sewanee Natural Bridge portions of South Cumberland State Park.

After passing through downtown, they come to an intersection where SR 2 splits from US 41/SR 56, through it is unsigned, and US 41/SR 56 then continue east and leave Monteagle.

They continue through countryside, passing by South Cumberland State Park visitor center and Grundy Forest State Natural Area portions of the park, before entering Tracy City, where SR 56 splits from US 41 to turn northward from Marion County into Grundy County, while US 41 turns south along unsigned SR 150.

SR 56 continues north, where it has an intersection with Greeter Falls Road (which provides access to the Greeter Falls portion of Savage Gulf State Natural Area (South Cumberland State Park)), and passes through Beersheba Springs, where it has an intersection with Stone Door Road (which leads to the Stone Door portion of Savage Gulf State Natural Area (South Cumberland State Park)), before becoming curvy again as it descends the plateau before traveling up a narrow valley, where it passes through Irving College and runs parallel to the Collins River, before crossing into Warren County.

It then proceeds north through a neighborhood before having a Y-Intersection with SR 8, before becoming E Colville Street and passing through a major business district and crossing a bridge over the Barren Fork River.

SR 56 continues north zig-zagging and crisscrossing atop various mountains and ridges before crossing a bridge over Center Hill Lake.

The highway then has an intersection and short concurrency with SR 290 in Center Grove before passing through some mountains and entering the town of Gainesboro.

Old Baxter Road and Main Street still function as major collector roads to this day, given that the Tennessee Department of Transportation designated them as an official detour route as part of their Interstate Incident Management Plan,[7] and they remain the fastest non-freeway route between Gainesboro and Smithville.

[8] The stretch of SR 56 between I-40 and Smithville was notorious for terrible curves prior to the late 1970s, but it was rebuilt and is now considered a good route to follow.