Upland Country Day School & Chester County Skating Club have been working together to offer constructive winter sports activities to boys and girls since 1969.   Both the Chester County Skating Club and the rink were projects spearheaded by Dr. John M. Cleveland, who served as Upland’s Head of School from 1962 - 1981 as well as chairman of the Chester County Skating Club for many years.  In 1993, following a successful fundraising collaboration between the School and the Club to update and renovate the facility, the Rink was dedicated to Dr. Cleveland.  Since then, the School and the Club have continued to work cooperatively to keep the facility updated and to maintain high quality skating programs for all ages.

The rink is also an integral part of the life of Upland Country Day School.  Beginning in Grade 1, Upland students skate as part of their physical education curriculum.  Boys and girls in sixth through ninth grade have the opportunity to participate in a vigorous ice hockey program which includes regional tournament play and biennial trips to Finland by our eighth and ninth graders.

The use of the rink by the community is extensive.  The facility is leased by the Chester County Skating Club, which uses the rink during nonschool hours.  About 75% of the time the rink is in operation is devoted to Club and community use.  The Club has a membership of 200 families, and fields twelve ice hockey teams—some 200 players.  The Chester County Skating Club also offers a figure skating program that culminates in an annual Ice Show.