Social Security application

Application date: July 18, 1938

Name: ROBERT TOWNSEND FLEETWOOD

Birth date: September 1, 1911

Birth place: Denton, Maryland

Father: Isaac Robert Fleetwood

Mother: Mary Elizabeth Townsend

Residence: 106 5th Street

Denton, Maryland

Employer: George Washington Hotel

10th Street and Boardwalk

Ocean City, Maryland

The Star-Democrat Easton, Maryland

May 7, 2006, page 13

ROBERT FLEETWOOD

CHESTERTOWN - Robert Townsend Fleetwood Sr. died May 4, 2006, at his home on Fey Road in Chestertown.

Born Sept. 1, 1911, he was the son of Isaac Robertson and Mary Elizabeth Townsend Fleetwood of Denton. After graduating from high school in Denton, he attended Washington College in Chestertown, where he played in the orchestra and jazz band. He also won many ribbons at track meets during his college career. He graduated in 1933, after which he worked for two years at Nuttle Lumber Company in Denton.

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 mathematic 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.

Bob Fleetwood was an active member of the music and arts community, playing trumpet in the Chestertown Band and directing the band 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 the 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 & County Club five times and won numerous other trophies at tournaments throughout the Delmarva Peninsula. He as 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 40 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.

Bob is survived by his two sons, Robert T. Fleetwood Jr. and wife Donna of Rockville and Richard Cregar Fleetwood and wife Lynn of Chestertown; two daughters, Virginia Leslie Fleming and husband Tom of Lancaster, Ohio and Elizabeth Earle Fleetwood of Bethesda; 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.

He was preceded in death by his wife of 62 years, Helen Claire Cregar Fleetwood (Washington College, Class of 1944) who passed away Oct. 18, 2005; and a brother, Carville Fleetwood, who died in 1973.

Services will be at noon on Tuesday, May 9 at Fellows, Helfenbein and Newnam Funeral Home in Chestertown, where friends may call two hours prior.

In lieu of flowers, donations may be sent to Kent County Community Marching Band, P.O. Box 912, Chestertown, MD; Hospice of Queen Anne's County, 300 Del Rhodes Ave., Queenstown, MD 21658 or to a charity of choice.

Arrangements by Fellows, Helfenbein and Newnam Funeral Home, Chestertown.

Denton Journal Denton, Maryland

April 28, 1944

Mr. and Mrs. I. R. Fleetwood had as their week-end guests Mr. and Mrs Robert Townsend Fleetwood, of Chestertown, who just returned from a wedding trip in New York State. Before her marriage, Mrs. Fleetwood was Miss Helen Claire Creagar, daughter of Mr. and Mrs. Charles Edgar Creagar, of Trenton, New Jersey. Both the bride and groom matriculated at Washington College, Chestertown, Maryland. Many friends and relatives attended their wedding, which took place on Saturday afternoon, April 8th, at 2:30 o'clock at the Prospect Presbyterian Church, Trenton, New Jersey. Mrs. Fleetwood wore a wedding gown of white taffeta trimmed with lace, and a fingertip veil caught with a coronet of rhinestones and seed pearls. Her bouquet was white gardenias. She was attended by her sister, Miss Betty Cregar, whose gown was light blue taffeta and whose veil was caught with a cap of light blue seed pearls. She carried pink rose buds. Mr. T. Carville Fleetwood was his brother's best man. Mr. James Cregar, of Easton, Maryland, and Charles Lufkin, of Trenton, were ushers. Immediately following the ceremony, performed by Dr. Hanzscke, there was a reception at the Cartaret Club. Mr. and Mrs. Fleetwood are now at home on Maple Ave., Chestertown, Md.

From Fellows, Helfenbein & Newman Funeral Home

FLEETWOOD SR., ROBERT

May 4 2006

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 hsi 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 F.A.M. & 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 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 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 Newman 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 21658 or to a charity of choice.