Giles Barrett "Barry" Montgomery

Giles Barrett Montgomery, 78, known to all as Barry, died unexpectedly on Tuesday, November 20th in Winchester, NH. Barry was born November 30th, 1939 in Stamford, CT to Eleanor Barrett and Giles Newton Montgomery. He received his bachelor’s degree in accounting at Duke University and subsequently served in the military reserves.

In 1967 Barry welcomed son Andrew Ruston Montgomery with wife Jill Ruston Montgomery. Barry was widowed too soon, in 1975. In 1990 Barry welcomed his daughter Katharine Barrett Montgomery with wife Anne Martin. He taught his children to be fiercely independent and kind and always encouraged them not to be afraid to live boldly.

From the 1960s to the end of his life, Barry was a successful and visionary real estate developer, creating Dolphin Cove and Old Stone Bridge in Stamford, CT among others. Barry lived in CT for most of his life and 20 years ago moved north to Western MA and most recently to Southern NH.

Barry was known for his dry wit, quick intellect, unending curiosity, and pure joy for life that radiated through his expansive smile and infectious laugh. He had a passion for development and architecture, reading books about religion and history, collecting and showing classic cars, and above all dancing, encouraging all he met to give it a try. Barry was active in local religious communities, leading Sunday schools and bible studies, attending Jewish ‘lunch and learns’, and was an active Mason.

Barry constantly and unconditionally gave to those around him in time, money, advice and encouragement. He was fearless in defending his values, a master of “creative” solutions, and in recent years had become especially adept at combining his passions with his desire to help. He saved old historic buildings, always overpaid at dances to ensure their continued success, loved taking his friends out to dinner, constantly brought new people into his dance and car communities, employed whoever needed work, and always participated in local events and organizations. Ultimately, his life was guided by his unwavering altruism, faith in others, and optimism about life.

Barry was predeceased by his father and mother Giles and Eleanor Montgomery and his first wife Jill Ruston Montgomery. He is survived by his brother Marshall Dean Montgomery, sister Anne Barrett Montgomery, former wife Anne Marie Martin, and his two children Katharine Barrett Montgomery and Andrew Ruston Montgomery, and daughter-in-law Carrie Miller Montgomery.

The family welcomes you to a celebration of Barry’s extraordinary life at the Guiding Star Grange, 401 Chapman Street, Greenfield MA on Saturday, December 1st. A reception with light fare will begin at 11:30 am for a 12:30 service, followed by more food, coffee and laughter. Any guests who wish to do so will be invited to say a few brief words during the service.

In lieu of flowers, memorial donation information will be provided at the service.