Richard James DeWitt


On Saturday, November 5, Richard James DeWitt, a beloved husband, father, grandfather, and son passed away unexpectedly. He was born to James and Gwendolyn DeWitt in Canandaigua, NY on October 4, 1954.

Rich spent his childhood in Needham, Mass. and graduated from Needham High School in 1973. After high school, he attended Plymouth State University in Plymouth, N.H. and majored in business. During his time at PSU, he was a four-year letter winner on the men’s soccer team.

His love for the sport of soccer continued throughout his lifetime. He was an active men’s league soccer player into his late 40s and also a licensed youth coach for several teams in Massachusetts.

Rich met Ann, his future wife, in 1978 in Rochester, N.Y. while he was in the Lincoln First Bank training program. They married in 1979 and recently celebrated their 43rd wedding anniversary. Shortly after marriage, they left Rochester and settled in Wayland, Mass. Rich initially worked for Shawmut Bank in Boston, but eventually joined Bear Stearns to follow his lifelong dream of working in the securities industry. He later became an institutional stockbroker for Alex. Brown and Sons, which was eventually acquired by Deutsche Bank. In 2007, Ann and Rich relocated to Athens, Ga. where Rich worked for Cannon Financial Institute. In 2018, after returning to Wayland, they relocated permanently to their summer home in Chilmark. At that time, Rich began working for Cape Cod 5 as a Wealth Manager supporting clients across Martha’s Vineyard, Nantucket, Falmouth, Wareham, and Plymouth. 

Rich was a cheerful, selfless, patient, and generous person. He was a community-minded individual who held leadership positions in various local organizations throughout his life. He devoted his volunteer time to this special Island community in his quiet but sturdy and fair-minded way of managing issues large and small.

He was an avid cyclist and fierce supporter of the cycling community on Martha’s Vineyard. Rich’s happiest days were spent organizing rides and cycling with friends. You might have seen him after work cruising by on a pre-dinner ride to Aquinnah. If you passed him, you always got that biker’s thumbs-up message as a sign of acknowledgement. He loved both road and gravel cycling, the latter of which allowed him to enjoy the serenity and quiet beauty of the Island. He passed away on a group ride on a beautiful Saturday morning in Manuel F. Correllus State Forest. Rich was chairman of the Martha’s Vineyard Commission’s Bicycle and Pedestrian Advisory Committee. He truly loved working with this group to make cycling safer for everyone on the Island. In addition, he served on the board of the Martha’s Vineyard Builders Association and was an active member of the Abel’s Hill Association, serving two terms as president.

He is survived by his wife, Ann, and three sons: John (Meghan), Charles, and Timothy. He was a loving grandfather, called “Scoop” by his grandchildren Emily and Ryan. Rich was predeceased by his father James DeWitt and is survived by his mother Gwendolyn and two sisters: Barbara (Jon) Deschenes and Nancy (Steve) Bamford, and many loving nieces and nephews.

There are no immediate plans for an in-person service memorial at this time, but there are plans to host a virtual service in the near future. There will be a memorial bike ride organized by the Cycling Club of MV in his honor along with a trail dedication on November 25 in Manuel F. Correllus State Forest. The ride will start at 10 am from the West Tisbury School. In lieu of flowers, memorial contributions can be made in Rich’s memory to TrailsMV at Sheriff’s Meadow Foundation, PO Box 1088, Vineyard Haven, MA 02568 or by visiting