Richard James DeWitt, a beloved husband, father, grandfather and son, died unexpectedly on Nov. 5. He was 68.

He was born to James and Gwendolyn DeWitt in Canandaigua, N.Y. on October 4, 1954. He spent his childhood in Needham and graduated from Needham High School in 1973. He attended Plymouth State University in Plymouth, N.H. and majored in business.

During his college years, 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 marrying, they left Rochester and settled in Wayland. 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 he worked for Cannon Financial Institute. In 2018, they relocated permanently to their summer home in Chilmark. He began work for Cape Cod 5 as a wealth manager supporting clients across Martha’s Vineyard, Nantucket, Falmouth, Wareham and Plymouth. 

He 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 of issues large and small.

He was an avid cyclist and fierce supporter of the cycling community on the Vineyard. His 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 died on a group ride on a beautiful Saturday morning in Manuel F. Correllus State Forest.

He 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.

He also 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 and his wife Meghan, Charles, and Timothy. He was a loving grandfather called Scoop by his grandchildren Emily and Ryan. He is also survived by his mother Gwendolyn; his sisters Barbara and her husband Jon Deschenes, and Nancy and her husband Steve Bamford; and many loving nieces and nephews. 

He was predeceased by his father James DeWitt.

A virtual memorial service will be held at a future time.

The Cycling Club of Martha’s Vineyard has organized a memorial bike ride and trail dedication for Nov. 25 at 10 a.m., beginning at the West Tisbury School. Information about the event can be found at Please sign up for online updates.

Memorial contributions can be made to TrailsMV at Sheriff’s Meadow Foundation, P.O. Box 1088, Vineyard Haven, MA 02568 or by visiting