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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.

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.

Apple Tree was a professional theatre company, one of only two in all of Lake County, serving over 30,000 patrons each year, including students in its Workshops. The Theatre won 28 Jeff Awards, with 109 nominations of various kinds, and sent many students and actors on to successful careers throughout the country, including Broadway.

Apple Tree Theatre was founded in 1983 by Executive and Artistic Director Eileen Boevers. Apple Tree Theatre was committed to producing dramas and musicals that "celebrate the tenacity of the human spirit and illuminate the human condition." In its 25th season, the theatre developed a reputation for producing high quality theatre, fortifying a relationship with its audience and artists alike. It was one of only two professional theatre companies in Lake County. It was located originally in the basement of Immaculate Conception Church in Highland Park, until 1988 when it moved to 595 Elm Place, Highland Park. 1988, Apple Tree Theatre also became an Equity Theater after 5 years of performing on special guest artist contracts with Equity.

Apple Tree Theatre produced four main stage shows and three Theatre performances, for Young Audiences productions, a year. A diverse audience of over 30,000 people all over Chicagoland attended its programs annually.
Apple Tree Theatre was honored with 109 Jeff nominations and over 28 Jeff Awards. In 1997, Apple Tree Theatre made history by becoming the only theatre ever to receive Jeff awards for both Best Play and Best Musical in the same season.

Moreover, Apple Tree was committed to providing a nurturing, creative environment for Chicago artists. Apple Tree employed over 200 artists annually as performers, directors, choreographers, musicians, designers, and teachers. Apple Tree consistently produced productions of a high caliber, albeit with modest financial capabilities, and became a home to accomplished artists, many of whom appear regularly on other well-respected stages, such as the Goodman, Chicago Shakespeare, Steppenwolf and the Marriott Lincolnshire.

In addition to its adult main stage season, Apple Tree produced a unique educational outreach program, Theatre for Young Audiences, which was committed to presenting works to an undeserved audience—the middle and junior high school age groups. Established in 1989, Theatre for Young Audiences presentations included stage adaptations of literature directly from the state mandated school curriculum, focusing on diverse themes with plays that incorporated multicultural sensitivity, the physically and mentally challenged, and other challenging themes such as the Holocaust. In 2005, The Theatre for Young Audiences was named one of the finest young people’s theatres in the state by the Illinois Theatre Association.

The Eileen Boevers Performing Arts Workshop (a third aspect of the Apple Tree Theatre) offered year-round classes in theatre performance, taught by instructors who work in theatre and were committed to building confidence, creativity, self-esteem, foundational skills, imagination, and a love for the arts. The Workshop trained thousands of young people, several of whom went on to Broadway or held other impressive theatre careers.

*Information for the biography on Apple Tree Theater was directly copied, with few alterations, from a poster in the collection that gives biographical information.

The Ravinia Garden Club was organized on August 16, 1927, by gardeners in a newly subdivided area of southeast Highland Park. Established to help educate the community in the art of gardening in the difficult conditions presented by the heavily forested woods and ravines that came to be the namesake of the community, founded as woman's club. Like other charitable Garden Club organizations of the era, they became well known for assisting with and sponsoring many horticultural related personal and civic projects throughout the years, often at the behest of the local, State, and Federal governments; in addition, to becoming a well-known philanthropic organization.

The Ravinia Garden Club nurtured initiatives beyond projects or public works. Endeavors also encompassed initiatives like the Garden Therapy project (which helped boost troops’ morale at Fort Sheridan during World War II), sponsoring youth education, and donating to botanical gardens and arboretums, and fund-raising for various other meritorious organizations and causes.

In 2017, members currently live in several communities in Lake county and elsewhere.

For a more complete history written by the organization, please see box 2.

Thirty-five business men of Highland Park met in the Hall of the Erskine Bank Building and formed an association, Monday evening Sept 19, 1910” A mission of “Home trade,” “mutual health” and attention to public needs led the fledgling organization to act within a broad mission of “betterment of the community.” Charles M. Schneider, who owned a store at 1815 St. Johns, served as the organization’s first president.

The Association sponsored events such as Highland Park Day, holiday festivities, charitable endeavors, and arts funding. Many significant financial contributions were offered to support opera and other programs at Ravinia Park.

The Association unanimously voted to change its name to the Highland Park Chamber of Commerce, August 10, 1925. This change broadened the organization’s mission, opening membership to public officials, educators and others. Notably, despite its name, the organization accepted woman business owners as members in its earliest days. The Highland Park Chamber of Commerce has traditionally been a member of the United States Chamber of Commerce, although its founding predates the national organization’s debut, April 12, 1912.

With the 21st century sobriquet, "Building Business…Building Community…Since 1911," The Highland Park Chamber of Commerce publishes and annual community guide, variously entitled, Organizations: Scope and Functions (1958); Who, What and Where and "Your Guide to Highland Park.” It also continues to sponsor an annual parade, the July 4th Kids’ Bike & Pet Parade; organizes an annual sidewalk sale and honors exceptional students annually.

The Chamber’s 2018 mission states: Our purpose is to help all member businesses prosper by providing programs and services to encourage business development through promotion, advocacy, connections and education.