During the reign of Dr. Ransom Dunn at Hillsdale College during the mid 1880s, the total segregation of the sexes was required at the school. Girls were to use one stairway in Central Hall, while boys had to use the other. The campus itself, by faculty ruling, was divided by an imaginary north and south line, allotting the east side to the women, the west to the men. Some boys, in turn, strung barbed wire down the middle of the central walk, then labeled each side accordingly.

Duke Ellington performed at the Hillsdale College "J-Hop" in 1949. In later years, the College hosted concerts by Kenny Rogers (with the First Edition), the Association, the Kingsmen, the Lettermen and Gladys Knight and the Pips, among others. Many of the concerts were held in the Davis Auditorium.

Esbon Blackmar donated the original twenty-five acres for Hillsdale College on the following two conditions:

1. That an institution of learning should forever be maintained thereon; and

2. That a majority of its Board of Trustees be residents of Hillsdale County.

The Hillsdale College ATO house on Hillsdale Street, formerly the Joseph Mauck home, was built by James Winsor in the 1860s. The original house was square, without the porticos of today, and painted bright red.

Common methods for earning one's way in the early years of Hillsdale College included "wood-chopping, pitching hay, corn-husking, and potato-digging."

When Professor Daniel Fisk arrived in Hillsdale in 1872 to accept a position at the College, he found "the front campus was a tangle of unknown weeds, littered with broken settees, cast-off chairs, and other rubbish—all a picture of slovenly neglect."

In 1881 the entire faculty of Hillsdale College joined the Michigan Temperance Society.

Hillsdale College students caught playing billiards were expelled by the College. 

In 1889 two horses were allowed to "bite off" the campus grass and were issued "grazing permits" by the College.

Hillsdale College was once advertised as being America's "Cheapest College."

from the Hillsdale Standard—February 22, 1866

"Three young ladies were on their way to the college, crossing the marsh below the Depot …. One of them was seized by a ruffian, she gave the alarm, when the other two who were in advance returned, and the scoundrel ran. He wore a soldier's overcoat and black wool hat. Ladies should be cautious about walking out alone evenings, unless they carry a pistol. If some of these impudent rascals should be shot down, they would only be getting what they richly deserve."

In a 1935 edition of the Hillsdale (College) Collegian, the new Field house was named a “white elephant.”

Carol A. Lackey