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John Finney moved to Warren Township, Illinois from New York State in 1852. Finney enlisted in the 65th Illinois Volunteer Infantry ("Scotch Regiment") and served three years in the Civil War theater. Elected Alderman of Highland Park in 1878 and City Clerk in 1880, he served four decades in city government. Finney also acted as Assessor of Deerfield Township for 12 years.

Hotel Moraine-on-the-Lake opened in Highland Park in 1900 to serve vacationing Chicagoans, many from the city's exclusive Gold Coast. Hotel Moraine was designed by Highland Park architect, Ernst Mayo, for F.W. Cushing and named for the nearby granite rock shelf. Originally open solely for the summer months, many guests spent their entire summer at the hotel. The Hotel operated at maximum capacity for its first 35 years, but was negatively effected by the stockmarket crash and subsequent Great Depression. In 1943 Jules Reingold, a wealthy real estate man from Glencoe, Illinois, bought the hotel and ran it successfully until his death in 1947 The Hotel changed hands several times between 1947 and 1963. In 1963, Richard S. Wright Enterprises purchased the hotel, capitalizing on the dining room and numerous meeting rooms to attract industry conferences. By 1968, the hotel was empty again. Illinois Bell rented and redesigned the hotel's garage to serve as a school for telephone operators. In 1969, Bert Schwarz purchased the land with intentions of tearind down the hotel and building a lakeshore high-rise. Moraine Citizens Committee, a group of Highland Park residents and politicians, mobilized to block the high rise development though a city wide referendum that would granted the City of Highland Park the funds to purchase the Moraine Hotel property for a future park and nature preserve. The original Hotel Moraine-on-the-Lake was demolished in 1972. In 1999, The Highland Park City Council proposed deeded the property to the Park District of Highland Park in hopes the park built where the Hotel Moraine-on-the-Lake will be better maintained.

In 1969, construction for a modern hotel began on a 4.5 acre parcel of land in Highwood, Illinois. The hotel opened in 1970 as a Ramada Inn franchise. Between 1972 and 1985, the Ramada Inn changed hands several times and becomes the Highwood Inn. In 1985, local restaurateur William Pigati purchased the Highwood Inn and renamed it the Hotel Moraine.

The first Highland Park High School classes were held at Elm Place School. One person graduated in the first class in 1885, Milton H. Baker, Jr. In 1887, the second floor of Brand's Paint Store on Central Ave. began to serve as the high school. Renamed Deerfield Township High in 1890, the school was called Highland Park High School colloquially until Shields Hall Opened in 1900. By 1904, the high school officially included students from Shields Township and became Deerfield-Shields High School. The 1936 opening of Lake Forest High School witnessed the return of the name Highland Park High School as Shields Township students began to attend Lake Forest High School.
The current Deerfield High School opened the late 1950s.

Born in Waynesville, Ohio in 1871, Harry Burton Roberts attended medical school in Chicago, Illinois (Jenner Medical College, 1902; College of Physicians and Surgeons of Chicago, School of Medicine of the University of Illinois; 1903). Roberts married Caroline Gertrude Brown of La Grange, Illinois on October 17, 1905. They lived in home designed by architect John VanBergen in Highland Park, Illinois. Roberts served in the Medical Corps of the United States Army in World War I after being drafted in 1917. Upon his return from service, he served as a lead physician at Highland Park Hospital; he also served a term as hospital president. JAMA, 1957;164 p. 788.