The majority of the materials in this collection are related to Helen's time at Greenwich Academy, including annual publications, two finished assignments, report cards, newspaper clippings, and ephemera related to riding competitions from her childhood. There are also materials relating to WWII; her husband Hawley T Chester Jr's U.S. Navy papers and orders, ration books, gas rations, and pages taken from her scrapbooks and put into file. There is also a short piece of correspondence between Greenwich, CT, and Greenwich, England, programs from the 1933 inauguration of FDR. Photographs reproduced from glass negatives, two copies of Greenwich Review, and a 1967 Civil Defense manual on fallout protection for homes with basements finish the collection.