She lived with her family on Adams Street in what is now called the Captain 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. On the 25th anniversary of the founding of Cunningham Park, Mr. Ge
orge Wigglesworth wanted to give a word picture of Mrs. Cunningham and had written: Picture to yourselves an elderly lady, with a face showing strong character, but radiant with kindliness and good will. Think of her as she came from her house in the morning in a little pony wagon drawn by a handsome black horse, which she herself drove. Think of her starting out on errands of kindliness, carrying flowers or fruit to the sick, or to those less fortunate than herself, or taking some child for an outing at Ponkapoag, Hoosic-Whisick, or Frenchs Pond, or perhaps taking children into the woods to gather wild flowers. And, speaking of children, do you realize that including nieces and nephews, great nieces and nephews, nieces and nephews-in-law, there were 125 people who called her Aunt Mary? And when the children went to her house there was always a large supply of delicious ginger cookies in the pantry, and in the dining room where Mrs. Cunningham sat, there was a cupboard full of childrens toys and childrens books. There was nothing ostentatious in what she did. It was not done in a way to attract attention, but it was far-reaching in the happiness it carried to others, and in the love which it won from them. Cunningham died in 1904 and left the bulk of her estate to three trustees, J. Malcolm Forbes, Nathaniel H. Stone and Thomas N.Perkins [t]o use at their discretion the principal and interest of said Trust Fund for some charitable object or objects which will improve the libraries and schools of said town, or which will promote the health of my fellow townmen by a aiding parks, playgrounds or hospitals within said town, or by making provision for my fellow townsmen in the hospitals of other places. The Trustees decided that the establishment and operation of a park would best satisfy Mrs. Cunninghams wishes. Her nephew, Edward Cunningham, who had been a partner in Russell & Company and made a fortune in The China Trade, had retired to Milton about 1857 and built the house that later became the Convalescent Home. Edward was killed in 1889 on his property by trespassers. The Trustees bought the estate from the heirs of Mr. The Park was opened in 1905 with two tennis courts, two bowling alleys and a gym remodeled out of a barn. The meadow in the back was flooded in winter for skating and for quite a while both the High School and Milton Academy played their hockey games there. The Convalescent Home moved from the corner of Thacher Street and Canton Avenue to the former mansion of Edward on August 3,1905. During this time it was largely funded by the Trustees, but after the hospital started the support of the Trustees was gradually withdrawn. For the first few years the Trustees operated the Park themselves, but in 1913 Jesse B. Baxter, President of the Blue Hill National Bank was added as Park Manager. Also, during this time Bill Caldwell was added to the staff and became the Director of Activities. Caldwell remained with the Park until 1957 and was there when the pool opened in 1922. When he retired he recalled, [t]eaching 1400 kids to swim has been my greatest accomplishment. The pool was named the Caldwell Pool in 1957. The bowling green was added in 1929 and was popular for many years along with a toboggan slide, badminton, basketball, horseshoes, motion pictures, shuffleboard and volleyball. Near the bowling green is an area where a flock of thoroughbred Shropshire sheep were kept for the pleasure of the children. There were also ducks, hens and occasionally pigs. The Trustees also operated a camp during the summer in Orleans Massachusetts that could accommodate twenty-eight girls per week. The camp began around 1917 with the majority of the girls coming from Milton and staying for about two weeks. In 1926 the Trustees gave the Town of Milton the land for a school and Collicott School opened in 1929. The land for Cunningham Junior High School followed in 1934. The next major changes that occurred were in the 1960s, when the pool was completely redone and the old gymnasium torn down. The pool had originally been a sand bottom and some people may recall the diving board with its high dive and low dive boards. The old gymnasium, that had been 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 new building was completed in late 1969.
