Cunningham Park exists today because of the generosity of Mary A. Cunningham. Born Mary Abbot Forbes in 1814, Mary lived on Adams Street in the house that is now the Forbes House Museum. She married the Reverend Francis Cunningham in 1843 and moved to 203 Adams Street in what is known as the Dr. Amos Holbrook House. She was very active in conducting relief measures for the troops and their families during the Civil War.

Mary was deeply committed to her town and community. Upon her death in 1904, she stipulated in her will that her fortune should be held in a Trust “for the benefit of the inhabitants of Milton.” Believing that open space for public recreation met this mission, the trustees purchased over 100 acres of land that had belonged to Mary’s cousin, Edward Cunningham. Cunningham Park was officially opened in 1905 and has been overseen by a trust which has operated and maintained the park and all of its amenities for over a century.

When the Park first opened in 1905, it offered Milton residents two tennis courts, two bowling alleys, and a gym remodeled out of a barn. Just like today, the meadow in the back was flooded in winter for skating, and for many years both the High School and Milton Academy played their hockey games there.

In 1926 the Trustees gave the Town of Milton land for a school and Collicott School opened in 1929. The land for Cunningham Junior High School followed in 1934. The swimming pond was completely rebuilt in the 1960s. The pond, which is primarily spring-fed, originally had a sand bottom and a diving platform with both “high” and low diving boards. The old gymnasium which served as the site of Milton Youth Club activities for many years was torn down in 1968. The last event held in the old gym was Bill Caldwell’s wake. The current Cunningham Hall building was completed in late 1969.

The AllTrails website has descriptions and maps of hikes at Cunningham Park.