[2] The first inhabitants of the area eventually comprising Montgomery County were Keyauwee and Cheraw Native Americans.

It was named in honor of Richard Montgomery, an American Revolutionary War general killed in 1775 while attempting to capture Quebec City, Canada.

Many residents were dissatisfied with the location chosen, and after several years of demurring on a decision, a courthouse was erected in the community of Henderson, created at the confluence of the Yadkin and Uwharrie rivers in 1794.

[6] Two years later, commissioners were selected to move the courthouse to Montgomery's geographic center, and in 1844 Troy was established as the county seat.

The Great Depression, which began in 1929, had a large adverse impact on the local agricultural and manufacturing industries.

[9] Montgomery is bordered by Davidson, Moore, Richmond, Randolph, and Stanly counties.

The Uwharrie National Forest encompasses a large swathe of the county.

[18] A county manager oversees most regular administrative activities and is responsible for executing the board's wishes.

The main east-to-west road route which crosses the county is North Carolina Highway 27.

[25] Freight rail service is run by the Aberdeen, Carolina and Western Railway, which operates an east-to-west line through the county which connects to Charlotte and Raleigh, and another which runs south to the Southern Pines/Pinehurst region.