My grandfather, St George’s businessman Henry Ernest Austin Dowling, has been dead for 55 years. One of my greatest regrets is that I failed to talk more with him. Yes, I visited him, took him for drives and stayed with him when my grandmother travelled abroad, but somehow I missed a golden opportunity to know more about him and our family. He was an interesting man and in an effort to redeem myself I have decided to write what I do know about him.

He was born in St George’s in 1883 to James Anthony Dowling and Sarah Catherine Smith. Many years ago, Fielding Swan described my great-grandmother as a sharp-tongued, dark-skinned woman who was always well-attired in fashionably long dresses and driven around St George’s in a carriage drawn by two horses — called “a double” in those days. My great-grandfather was employed by John S. Darrell as a master stevedore and foreman in charge of the coal for the ships that sailed into St George’s. Around 1910, they rented Tucker House, on Water Street, which was directly opposite the docks. At that time, Tucker House was owned by Emma Boggs, who ran a grocery store on the corner of York Street and Queen Street. She later moved her business to where Robertson’s Drugstore is now located. Two years after the death of my great-grandfather in 1918, the family moved and Mrs Boggs returned to live in Tucker House.

In the late 1980s, Crescent Swan, a 99-year-old resident of Lefroy House, asked if I was related to the Dowlings of St George’s, as he could see a family resemblance. He then happily informed me that as a young man he had been employed on the St George’s docks and boarded at Tucker House with my great-grandparents.

In 1896, when my grandfather was 13, he went to work on the Sylvester Farm located in the Cut Road area of St George’s, where onions and potatoes were grown and crated for export. He worked from sun-up to sundown, earning ten shillings a week. He retained one shilling for himself and gave nine to his mother to put into the Custom’s Bank, later known as the Post Office Savings. When the savings amounted to 50 pounds, he purchased his first piece of property overlooking Tobacco Bay, and built a house.

The older men employed on the farm worked similarly long hours, but on Saturdays and Sundays, they became fishermen.

In his early twenties, he married Inez Mae Butterfield, the daughter of Mr and Mrs James Peter Butterfield. The family lived in Buckingham, King Street, St George’s, where her father ran a tailoring business on the lower floor. One of his apprentices, Norris Dowling, moved to America, where he became the valet for the American film star Lionel Barrymore.

My grandparents had six children.

Henry Dowling’s desire to own his own business came to fruition when he became a cobbler and opened a store on York Street across from the police station. He not only made and repaired shoes, but also imported a simple canvas-top, rubber-sole shoe with a reinforced toe called a plimsoll.

When the St George’s Hotel opened in 1906, he added a shoeshine component to take advantage of the ever-increasing tourist business.

Across the street a Mr Jones, assisted by “Rooster” Richardson had a business renting Raleigh pedal cycles to tourists. He owned only six. Henry Dowling observed from his cobbler shop that Mr Jones did not have sufficient bicycles to meet the demand. Seeing this shortfall led him, in 1914, to purchase two dozen pedal bikes. The rental business flourished to the point where it became the business and Dowling’s Cycles was born.

In the beginning, he carried Challenger and, later, Elswick and Evinrude bicycles. By 1953, he began to rent and sell Velosolex Automation bikes, and brought his sons Howard and Randolph into the business. Howard would travel periodically to France to order bikes while Randolph managed the business. In more recent times, Randolph secured the dealership for Kawasaki motorbikes and jet skis.

Albert Dismont, owner of Dismont Cycles in Hamilton, and Henry Dowling were friends and business associates. They would travel together to New Jersey to purchase retired racehorses for their carriages. My mother often recalled attending parties in carriages driven by these horses. Dressed in all their finery, they would hastily get into the carriage with her brother, Sidney, controlling the horses. He would release the horses and they all hung on for dear life on one hell of a ride to Spanish Point. My cousin, Edric Pearman, added that my Uncle Sidney could only be described as a daredevil. They would go horseback riding, with my mother insisting she be a part of the excitement; otherwise, she would, “tell on them”. They would ride bareback through St George’s with my mother sandwiched in the middle on an exhilarating but highly dangerous race around the parish.

In later years, the carriage houses and stables at the rear of his Queen Street residence were renovated to accommodate his taxi business and more recently converted into apartments.

By the mid-1920s, Henry Dowling was a prominent St George’s businessman. He sold his house overlooking Tobacco Bay, moved to Seven Gables, which was owned by the MacCallans and conveniently located adjacent to his bicycle business on York Street. He later purchased Croton Villa on Queen Street, renovating it to accommodate his ageing mother, and resided there until his death in 1968.

He was always aware of the value of a good education for Black children in segregated Bermuda. He saw the inadequacies and towards this end, he met with William Cooper, a Member of the Colonial Parliament, W.R. Perinchief and other St George’s businessmen to pressure the Board of Education to employ a trained principal to improve the standard of education for children in the parish. Their request was approved and by 1929, Charles C. Snaith arrived from Jamaica to assume the principalship of East End School.

In the 1930s, the famous boxer Joe Louis arrived in Bermuda. He was booked to stay at the Hamilton Hotel but because of the colour bar, he was denied accommodation. My grandfather was contacted regarding this unfortunate situation and Mr Louis was immediately transported to be accommodated at the family home in St George’s.

For many years, he was the treasurer for St George’s Cricket Club and in 1933 was elected as its president. He was a member of the Alexandria Lodge 1026 of the Grand United Order of Oddfellows, described as one of the Black lodges. He was a member of the Corporation of St George, served on the vestry of St Peter’s Church and was one of the pioneers of the Quality Bakery.

I was their first grandchild and was sent from Somerset to spend part of my summer holidays in St George’s. I spent my day gathering thistles to feed the chickens, visiting my uncles at the bicycle shop, running errands to Outerbridge’s Grocery store with the money securely tied in a handkerchief and frequently to Robertson’s Drugstore’s lunch counter to purchase Claudine Smith’s chicken salad sandwiches, a favourite of my grandmother.

I was always puzzled as to why my grandmother had me up at the crack of dawn to go with her to the beach. I wondered why we walked past Tobacco Bay to end up at a little beach, which was quite a walk from Queen Street. In later years, I tried to find this beach, but it was not until I visited Fort St Catherine, looked down and there it was — Achilles’ Bay. Only recently I realised that my grandmother, in her quiet way, was defying the system. That beach had been designated for the White tourists staying at the St George’s Hotel, and not for locals looking like us. By going at dawn, she could bathe at her favourite childhood beach undisturbed and unnoticed.

Henry Dowling invested his profits in modernising his cycle business and into real estate. By the late 1930s and 1940s, he was renting the majority of his holdings to service personnel from the Kindley Air Force Base. By all accounts, it was a very lucrative investment.

He was one of E.F. Gordon’s closest friends and confidants. As a little girl, I remember seeing Dr Gordon standing across from where the Bermuda Industrial Union petrol station is located today. He was dressed in an overcoat, scarf and felt hat, awaiting a ride from my parents. They were going to St George’s to meet my grandfather and other planners and supporters of his candidacy in a by-election. I sat silently in the back of the car with him and my doll, Esmerelda, as they discussed matters I was too young to comprehend. Today, I understand it was all related to their desire to correct the inequalities on the island by preparing him to run as a candidate in a forthcoming by-election in St George’s.

On the evening of March 5, 1946, hundreds attended a town hall meeting encouraging voters to support Dr Gordon. He was nominated by my grandfather and seconded by John Wright. The other candidate, Charles Hilgrove Fox, withdrew and Dr Gordon ran unopposed.

Unfortunately, he was defeated in the election of 1948.

William “Willie” Paynter, his wife, Blanche, and family lived in the house immediately beside my grandparents on Queen Street. The two families were fast friends and firm believers in the Bermuda Workers Association, and were vocal supporters of Dr Gordon.

In the election of 1953, Dr Gordon was scheduled to run as a candidate for Devonshire, where the merchants knew he would be defeated. A shrewd group, which included Henry Dowling, William Paynter and other supporters, had a well-guarded plan — he would run in St George’s instead. Five minutes before the closing of nominations, Dr Gordon handed his nomination papers over to William Paynter, who raced over with the documents giving the merchants no time to nominate anyone else. Dr Gordon was seconded by William Paynter.

Dr Gordon won the seat, but this enraged the business community of St George’s and Mr Paynter, who had been employed as a butcher at Spurling’s Meat Market for 13 years, was quickly and unceremoniously fired in an act of retaliation.

The people of St George’s were enraged by this decision and gathered in the hundreds in Market Square to hear an address on the dismissal by the recently elected Dr Gordon. Police surrounded the area in anticipation of trouble, but Dr Gordon advised the restless crowd to remain calm and to boycott Spurling’s Meat Market. And so they did.

William Paynter went on to build and open his own grocery business towards the front of his house on Queen Street. Today it no longer exists.

My grandfather was a slim, brown-skinned man who was not very tall. He was seldom seen without his felt hat, and in later years he walked with a cane. He had a pronounced limp, which my mother said came as the result of a kick from a cow in his youth. Through his real estate holdings and successful business ventures, he became a Black millionaire.

When I returned to Bermuda in the mid-Sixties, I was offered a position with the Bermuda Welfare Society. My grandfather was not at all pleased, as he was familiar with its past discriminatory practices and was very vocal on the issue. He then proceeded to remind me that the women in this family never work for other people, and took to his bed claiming an attack of gout. I did accept the position and we never discussed the issue again.

When we gathered for Christmas dinner in 1967, he quietly asked me to join him in the kitchen. He wanted to show me how to carve a turkey. “You’ll need to know this to help your grandmother next year,” he said. Three weeks later, he was dead.

I frequently think of him, but more so on Christmas Day when we sit to the beautiful dining-room set he ordered in 1927 from Macy’s in America and shipped to Bermuda as a Christmas gift for my grandmother, his beloved Inez.

Dowling’s Cycles passed to his sons, Howard James Dowling and Henry Randolph “Buster” Dowling, who sold it in 2002 to Oleander Cycles.

• Cecille C. Snaith-Simmons is a retired nurse, historian, writer and author of The Bermuda Cookbook. Much of the information in this article was gleaned from Henry Dowling’s oldest child, Thelma Packwood, her aunt, who died in 2007 at the age of 99

References:

Dr E.F. Gordon: Hero of Bermuda’s Working Class (Dale Butler 1987)

Mazumbo One Hundred Facts and Quotes by Dr Gordon (The Writers Machine Jacks Series 3)

The Royal Gazette (January 17, 1968)