On the recommendation of a professor friend, Roberts enrolled as a freshman at the University of Chicago at the age of 36 in 1917, avidly studying literature and philosophy and fulfilling a lifelong dream of acquiring a college education.

At the University of Chicago, she joined the Poetry club which included Glenway Wescott, Yvor Winters and Janet Lewis forming friendships and professional relationships.

She went on to write several more successful and critically acclaimed novels throughout the 1920s and 30s, including The Great Meadow (1930), an historical novel about the early settling of Kentucky; A Buried Treasure (1931), about a rural Kentucky farm family who finds a pot of gold; He Sent Forth a Raven (1935), which reflects the contrasting World War I era ideological forces, and Black Is My Truelove's Hair (1938), the story of a shamed woman's return to her home village and restoration.

After this blow, Roberts began spending her winters in Florida; however, she returned to Springfield for the warmer months, writing and meeting family responsibilities.

In 2012, Dr. Victoria Barker, an English professor at Carson-Newman College, edited a previously unpublished novel by Roberts titled Flood.