Around the beginning of the twentieth century, Monterey was a resort town that boasted seven hotels and drew summer people who came to enjoy the cool temperatures and mountain scenery.
With the invention of the automobile, Monterey became less of a resort town. The hotels closed and the town's economy became dependent on railroad maintenance, coal mining, and logging.
The Standing Stone was a -tall rock that once stood upright on a sandstone ledge in the area. It was the legendary boundary between Cherokee and Shawnee territory and marked the Cherokee Tallonteeskee Trail. The remnant of this stone is preserved in Monterey, where a Standing Stone Celebration of Native American Heritage is held each October.
The red brick Monterey High School building was torn down in early 2013; a new high school is currently under construction where the old building stood.