Frederick C. Aldrich is credited with first suggesting, during the fall of 1900, the formation of “a club for winter sports to be located somewhere near the center of the village.”  To test the popularity of Mr. Aldrich’s suggestion, the land on which the Winter Club now stands was leased, with the option to buy, for the winter of 1901-02.  An outdoor skating rink was prepared along with a toboggan slide, which crossed over Sheridan Road.  The Winter Club rink quickly became the center of all social activities that first winter, as skating, curling and tobogganing entertained young and old.  The season concluded on February 15, 1902, with the first Winter Carnival.  It is reported that “immediately after the carnival the original founders of the club got together to plan for a permanent organization.”

On March 17, 1902, a circular was sent to both citizens and summer residents of Lake Forest proposing construction of a clubhouse costing $8,000, which was to be built on the leased land that had already been purchased for $9,000.  A sketch of the clubhouse designed by architect Alfred H. Granger, one of the founding members, was included.  The circular further described the clubhouse facilities as including, “. . . a ‘room’ large enough to accommodate comfortably an audience of 200 people and suitable for large private entertainments such as musicals, receptions, dances and lectures.  There will also be bowling alleys in the basement.”

The Winter Club’s letter of incorporation, which was filed with the State of Illinois on July 8, 1902, specifies a capital stock of $15,000 and further states that the objective of the organization is “to provide facilities for games and amusements and to instruct the members of said Corporation, their friends and families, in the arts and sciences.”  This letter of incorporation was signed by Sydney Richmond Taber, Edward M. Samuel and Edward F. Gorton.

The Winter Club building was completed in the fall of 1903 and looked very similar to the clubhouse as it stands today.  Squash courts and the swimming pool were built in 1926 and 1927.  Then in 1937 the tennis courts were covered with an asphalt surface, replacing the clay and gravel surface that caused many a scratched knee.  The artificial ice rinks were a major capital expenditure for the Winter Club in the late 1959 and again when it was renovated in 1989.  The swimming pool was relocated to its present location in 1968.  Racquet sports have grown over the years: platform tennis was introduced at the Winter Club with the construction of two courts in 1976; two additional tennis courts were constructed in the front of the clubhouse in 1985; a third platform court was added in 1991; a fourth platform court was added in 2017; and the Paddle Hut renovated in 2018 with the addition of two fireplaces and a large deck..  However, perhaps the largest capital project was the renovation of the original clubhouse completed in 1996.

From inception, The Winter Club’s programming has provided athletic and recreational activities for its member families.  The Winter Club operated primarily as the athletic extension of the Bell School throughout the 1930’s and 1940’s.  As one historical document reports of this period, “a balanced and continuing program for all ages (5-13) was conducted throughout the year.”  With the merger of the Bell School and Lake Forest Country Day School in 1958, the Winter Club’s focus changed from providing the year round athletic activities for members’ children to providing supplemental winter and summer seasonal activities for children.  Both winter and summer programs were enhanced at this time.  During the 1960’s the Winter Club sponsored a waterfront program at the Lake Forest beach, which included sailing instruction using the Club’s two sailboats.  The expanded activity program included lacrosse, slot car racing, soccer, field hockey and, of course, tennis.  The ice hockey program reached a pinnacle during the 1960’s as Winter Club teams participated competitively at national tournaments.  In 1965 and 1968 the Winter Club Bantam Hockey team won the State Championship and went on to compete in the National Championship in Lake Placid, New York (1965) and Edina, Minnesota (1968).