Miles Cutler Webb was born in West Brookfield on July 18, 1899 to John Henry Webb, farmer, born Worcester, and Carrie Etta (Cutler), born West Brookfield. He received his education at Worcester Academy, Brown University, and Harvard Business School and returned to West Brookfield to work on the family farm until he found employment with Ware Trust. Co.
Miles married his wife Gertrude about 1928. She became the proprietor of Open Hearth Tea House located on East Main St. in what had been the Austin Phelps House, in June of 1929.
Mr. Webb was an Assistant Treasurer for Ware Trust Co. in 1936 and was appointed chairman of the agricultural committee of the Massachusetts Bankers Association. He retired in August of 1964. Active in town affairs, he served two terms as a selectman in West Brookfield and later served the town as moderator. He died in June 1987.