The children of the earliest settlers of the area—like the Consauls, Markerts, Everts, Rabes and Grams—had to walk several miles to Town of Milwaukee Schools. As the population grew, parents petitioned the Town of Milwaukee Board for a new school closer to the area – but to no avail. George A. Rogers who published a weekly newspaper, The Whitefish Bay Pioneer, began a campaign for a village charter so that a new school district could be established. He received enthusiastic support and after several meetings a decision was made to incorporate the community as a village. The first step was to prove that the 300-people required by state law lived within the limits of the proposed village. Henry Scheife was given the job of making the official census. was to prove that the 300 people required by state law lived within the proposed limits. Henry Scheife made an initial census, but came up short. The boundaries were extended—hence the jog in the southern boundary of Whitefish Bay. Scheife’s count completed in March 1892, showed 70 houses and 312 people. A petition accompanied by the census was submitted to Judge Johnson who on May 10, 1892 signed the order bringing the village of Whitefish Bay into existence. Officials were elected on June 5th of that year. One of the first orders of business for the first Village president, Fred Isenring, was to appoint a school committee. The Committee prevailed upon the owners of the triangle now bounded by Idlewild, Fleetwood and Marlborough to donate the tract for a new school house. While the new school was constructed, Whitefish Bay kids had classes in the Jefferson Park pavilion on the site of the present Henry Clay School until it got too cold for comfort. Then school adjourned to the Scheife grocery store, located where Winkies now stands. The new school building was completed in late spring and dedicated on June 23, 1893. Mrs. Alice Curtis, the first teacher, received the princely sum of $60 a year (while Nicholas Rix, the janitor, was paid $75).

Tragedy hit the Fleetwood Whitefish Bay school in 1918—the building caught fire and quickly was lost. Some say that a flying ember from the near-by rail tracks was responsible—others disputed that source. In any case, the Village had a dilemma. It had to find an almost immediate replacement.

Land was available on the Port Washington and Whitefish Bay Road, now known as Henry Clay Street, on the site of the former Jefferson Park pavilion. Plans were immediately drawn up and construction commenced. It was initially occupied in 1919.

The Henry Clay School was a grade school, although that changed starting in 1930 when Shorewood notified the Village that it would no longer accept students from the Village. Whitefish Bay again had to find an immediate solution. One wing of the Henry Clay school was devoted to Whitefish Bay high school kids. They continued there until the new high school building was available for occupancy in 1932.

An eight-room addition was added to the Henry Clay School in 1951. It remained largely that way until 1980 when it was closed and converted into a community center.

In the 1980s, the Whitefish Bay school board began investigating the advantages of creating a middle school format and ultimately decided to proceed. The Henry Clay School was converted into a middle school and opened in August 1989. A new gym was added at that time. In 1991 the stage of the old gym was converted into two classrooms and a classroom was added to the basement level.

A 1994 Village referendum to add classrooms and other space to eliminate overcrowding was defeated; consideration is given to moving 8th graders to the high school. The following year the school board revised the expansion plans and hired a public relations firm to assist in the passage of a referendum to add classrooms and other space. The referendum passed narrowly (2980 for/2898 against). With the passage of the resolution, the additions proceeded. The school was re-named the Whitefish Bay Middle School.

The community and its residents have worked to create and support a strong school system that has generated great results. At the same time, a number of exemplary private schools have also flourished in the Village.

Other retail stores quickly followed. Some continue to serve the community after many generations. Others closed as the nature of retail commerce changed over the years.

Many of the stores on Henry Clay Street have closed and have been replaced by apartment buildings when the character of the district changed. The Silver Spring shopping district, however, continues to serve the community well with a diverse mixture of retail establishments.

• Images of Whitefish Bay, Arcadia Publications, Thomas H. Fehring, 2010.
• Chronicles of Whitefish Bay, WI, The History Press, Thomas H. Fehring, 2013.
• Historic Whitefish Bay: A Celebration of Architecture and Character, The History Press, Jefferson J. Aikin and Thomas H. Fehring, 2017. Published to help commemorate the Village’s 125th anniversary.

All three books are available for loan or purchase at the Whitefish Bay library. They are also available at local stores and other booksellers.