Robert Fleetwood Sr.

Robert Townsend Fleetwood, Sr., died May 4, 2006 at his home on Fey Road in Chestertown. He was born September 1, 1911 the son of Isaac Robertson and Mary Elizabeth Townsend Fleetwood of Denton, Maryland. After graduating from high school in Denton, he attended Washington College in Chestertown where he played with the orchestra and jazz band. He also won many ribbons at track meets during his college career. Following his graduation in 1933 he worked for two years at Nuttle Lumber Company in Denton, Maryland. In 1935 he returned to Chestertown to begin his teaching career at Chestertown High School where he taught until 1945. Most of the senior citizens of Chestertown remember Mr. Fleetwood as either their mathematics or chemistry teacher, however, he taught many other subjects as needed. He was a beloved coach and mentor to many. Reunions were high points in his life and he tried to attend all of them. In 1946, after leaving the field of teaching, Bob Fleetwood began a new career as an insurance agent, opening the Kirby-Fleetwood Insurance Company with Jim Kirby. This company evolved into the current FAM&M Insurance Agency in Chestertown where his grandson, Creg, a 2003 Washington College graduate, is currently an agent. Mr.Fleetwood was an active member of the music and arts community where he played trumpet in the Chestertown Band and was the Director for one year. He was one of the original members of the award winning Kent County Community Marching Band, playing the trumpet and marching well into his 80’s. He also played Taps at many funerals. During his teaching and business careers, he was active in other aspects of the community. He was President of the Chestertown Chamber of Commerce, a Board member of the Chestertown Volunteer Fire Company, and a Board member of Chester River Yacht and Country Club. As a self-taught oil painter, Mr. Fleetwood painted local landscapes, portraits, and still-life paintings. He shared that love of painting as a member of the Chestertown Arts League where he served as treasurer. An avid golfer, Bob Fleetwood was Club Champion at the Chester River Yacht & Country Club five times and won numerous other trophies at tournaments throughout the Delmarva Peninsula. He was also the Golf Professional at Chester River Yacht & Country Club in 1949. In 1960 he traveled to Augusta, GA to attend The Masters Golf Tournament at the Augusta National Golf Club. He then became a patron of the tournament for over forty years. Mr. Fleetwood’s interests and accomplishments extended far beyond golf and community; he excelled at many endeavors including pool, chess, and tennis. He was an avid and knowledgeable gardener and maintained a large vegetable and fruit garden for many years. He was married for 62 years to Helen Claire Cregar Fleetwood (WC class of 1944) who passed away on October 18, 2005. His brother Carville Fleetwood died in 1973. Bob is survived by his two sons; Robert T. Fleetwood, Jr. and wife Donna of Rockville, MD, Richard Cregar Fleetwood and wife Lynn of Chestertown, and two daughters, Virginia Leslie Fleming and husband Tom of Lancaster, Ohio, and Elizabeth Earle Fleetwood of Bethesda, MD; four grandchildren, Susan Fleming Cross and husband Thom, Tom Fleming V and wife Maggie, Lauren Elizabeth Fleetwood, and Richard Cregar Fleetwood, Jr.; two great-grandchildren, Emily Claire and Thomas Michael Fleming VI and several nieces and nephews. The Fleetwood family will be gathering to greet friends on Tuesday, May 9, 2006 from 10:00 A.M. to 12:00 at Fellows, Helfenbein and Newnam Funeral Home in Chestertown. Services will be held immediately thereafter. In lieu of flowers, donations are requested to be sent to Kent County Community Marching Band, P.O. Box 912, Chestertown, Maryland, Hospice of Queen Anne’s County, 300 Del Rhodes Ave., Queenstown, Maryland 21658 or to a charity of choice.