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Memories & Candles

“Deepest sympathy to Peter, Danny, Charlotte and all their families. ”
1 of 4 | Posted by: Jonathan Surgenor

“Dear Charlotte, Dan & Peter, I have missed your mother dearly, I loved her and love you all, that won't end. God bless you, Nancy ”
2 of 4 | Posted by: Nancy Blackett - Friend

“To a real Class Woman. May she rest in peace and we will miss her friendly smile. ”
3 of 4 | Posted by: Robert Kelly

“I went to Charles River School with Madeline. She was class of 1943 and I was class of 1942. We remained friends throughout the years, though I moved...Read More »
4 of 4 | Posted by: Pamela Richmond Orr - School

Madeline L. Gregory, of Westwood, MA died May 16th, 2022.

Madeline was often referred to as "Mad." In fact, no nickname was further from her nature. She greeted everyone with warmth and genuine caring. Her openness towards others is noted by those that knew her well or had only met her once; she made people comfortable. Her life was devoted to selflessly showering her grace and love on friends and family. She loved all sports including tennis, skiing, sailing, or golf, taking them on with a competitive energy that belied her genteel demeanor. She loved watching her beloved Red Sox from the first game of spring training through whatever end the team had in the Fall.

Madeline was born in Boston and lived almost her entire life in Westwood. She graduated from Charles River School (1939) and Milton Academy (1943). She remained loyal to those schools in many different capacities. She was a Trustee at Milton Academy, member of the Board of Directors of The Trustees of Reservations, a Trustee of the Faulkner Hospital, and a Warden of St Paul's Church.

Madeline was predeceased by her late husband, Daniel S Gregory. They enjoyed a true partnership for 58 wonderful years, traveling widely, cruising in Maine, spending summers on the Cape, and attending to a growing brood of grandchildren and great grandchildren. She was the loving mother of Charlotte G. Surgenor and her husband Tim of Dover; Daniel S. Gregory Jr. and his wife Mary of Cambridge; and Peter S. Gregory of Dedham. She was sister of Kathleen B. Sherbrooke of Cohasset, and David S. Lee of Brookline. She is also survived by eight grandchildren and six great grandchildren, and many nieces and nephews.

Relatives and friends are invited to attend a Memorial Service at St. Paul's Church, 59 Court St., Dedham MA on Tuesday June 7th, at 2:00pm. Interment will be private. The service may be viewed on zoom:

In lieu of flowers, donations may be made in memory of Madeline to the Charles River School, to support Financial Aid, Box 339, Dover, MA 02030.