This article was taken from our archives. It first appeared in the May 1984 issue of The Bermudian. It appears here as it did originally.

At the eastern end of Hamilton Parish, just before our causeway and the airport which links us with the rest of the world, lies an unspoiled, rural community known as Bailey’s Bay. Today, many of us pass quickly through Bailey’s Bay in our motor vehicles, glancing indifferently at its historic treasures, its age-old beauty. A hundred years ago and more, when the pace of life was slower this remote place became a whole world to the families who lived there. The Bailey’s Bay people centred their lives around their Church, their relatives and families – those things they knew and trusted.

These gentlefolk, who lived apart from the rest of Bermuda, were often poor and hard-working; and yet they believed in education, were cultured and well-read, and, in their own way, kept pace with the rest of the world.

During the long, hot summer days, when all the men were out farming in the fields or clearing the cedar woods for shipbuilding, the lazy clip-clopping of horses on the sanded roads, or the merry laughter of children playing in a distant garden, were about the only sounds to stir the gentle quiet. The sudden buzzing of a wayward bee, flying in at the bedroom window, could quite startle one. And in the winters, when the gales blew hard from the north-east, whistled round gables and rattled windows, the Bailey’s Bay people were safe and warm in their sturdy homes which had harboured them from storms and sorrows for generations.

It is through the vivid accounts of the late Miss Anna Maria Outerbridge of ‘Willoughby’ in Bailey’s Bay, that the past becomes alive for us. Miss Outerbridge was born at ‘Willoughby’ in 1848. The daughter of Dr Thaddeus Outerbridge, she made careful notes of her life in old Bailey’s Bay, and these have survived safely in the archives of Mr. William E.S. Zuill of ‘Orange Grove’. Anna Maria died in 1928, and these written memories are a testament of her life and all she believed.

Life in Bailey’s Bay chiefly centered around the Outerbridge family. The late Mrs Julia E. Mercer, genealogist and historian, remarked that, “Without Outerbridges there would have been no Bailey’s Bay.” The two names are almost synonymous, really. “There have always been more Outerbridges in that part of Bermuda than in any place else, and they doubly outnumbered all of the other Bailey’s Bay families in their name alone. They go back a long way in our history,” Mrs Mercer noted.

All of the Bailey’s Bay Outerbridges trace their descent from The Honourable Thomas Outerbridge, who died in there in 1692. Thomas was a judge of the Court of Vice-Admiralty and served on the Governor’s Council from 1688-1691. He worked as a shipwright. Miss Anna Maria describes the estate of her ancestor, Thomas “as being about eighty-four acres with good farm and grazing land in the hills and valleys above the Bay.” This would have encompassed all of the property west of Holy Trinity Church Road, up to where the Clay Estates are now, and over to Harrington Sound. Thomas Outerbridge’s house, now gone, was built in the cruciform style (shaped like a cross) half-timbered in cedar and probably thatched in palmetto leaves, originally. Miss Anna Maria makes an interesting description of this early Outerbridge house by referring to an extensive inventory made of Thomas Outerbridge’s effects following his death: “The house was comfortably furnished. To the west was a large, enclosed room called the ‘porch’. From this one entered the ‘hall’, the main room in the centre of the house where the guests were received.” (We would call this the living room today.) “The ‘hall’ was furnished with two tables, high-back chairs, framed chairs with cushions, and settles. Opening off this room to the north, one entered a large, handsome room called the ‘parlour’. Friends and honoured guests were received here and this is where Thomas and his wife slept. The ‘parlour’ was furnished with a handsome bed draped with the best material obtainable, cedar chests, cedar chairs, and a glass case containing earthenware. A ‘chamber’ with bed furniture for the children was situated at the southern end of the house, and this had an‘outlett’, a little room with outside windows. There was also a dining room at the eastern end containing a large table, silver tankards and flatware, and much pewter. The pantry, kitchen, milk-house and servants’ quarters were separate from the main house. Poultry and pigs were confined to the courtyard. Cattle, horses, sheep and deer roamed in the fields which were fenced in. The Outerbridges kept the deer, which they imported from Virginia, as pets.”

‘Willoughby’, where Miss Anna Maria lived, was originally called ‘The Lodge’. This is the two stoned imposing white house just above The Bay. The oldest part of ‘Willoughby’, where the middle portion of the house now stands, was built in the early eighteenth century by Colonel William Outerbridge, Chief Justice of Bermuda who was a younger brother of Thomas, mentioned earlier. “Colonel Outerbridge started in life with only £20, some farm land, two slaves, a good bed, two chests and a silver caudle cup, willed to him by his father in 1676,” Miss Anna Maria notes, “and he ended up the most prominent man in Bermuda.” The Colonel died in 1724. ‘Willoughby’ later passed to one Perient Trott, whose family had once been the largest land-owners in Bailey’s Bay. After 1760, when Perient’s daughter Mary married William Outerbridge, a great-grandson of Thomas, ‘Willoughby’ and its property came back into the Outerbridge family. “Some fifty years ago,” Miss Anna Maria continues, “My elderly relatives remarked that they remember hearing their grandparents say that William Outerbridge and Mary Trott were the most handsome and best dressed bride and groom who ever attended Holy Trinity Church.” William and Mary were Miss Anna Maria’s great-grandparents. She describes William as a merchant in St. George’s, and notes that “his tastes were refined; he liked good books, good living and fine apparel and he considered drinking and gambling low and degrading and never indulged in either habit. William Outerbridge represented his Parish in the Assembly which met in St. George’s. For some years he had a grocery business in St. George’s, and during the American Revolutionary War he was remembered for a particular act of kindness to the Bermudians. The Revolutionary War affected our people very seriously. There was an embargo placed by the Americans on all foods leaving their country for British ports and flour consequently became very scarce in Bermuda. However, William Outerbridge was fortunate to have a large supply of this, but instead of raising the price and selling at a big profit, he continued to charge the same as before.”

On up the hill from ‘Willoughby’, on Holy Trinity Church Road, is ‘Cedar Grove’ where Captain William Thomas Outerbridge lived. He was the eldest son of William and Mary and was Miss Anna Maria’s grandfather. He named his house for a handsome grove of ancient cedars which lined from the path leading to the house from the main road. ‘Cedar Grove’ originally consisted of two rooms which had been built during the 1740s under the Trott family. The Trotts opened a school there which closed after a short time. William Thomas Outerbridge bought the building and its adjoining property about 1790 and added to it, thus making it a fine house for his family.

“William Thomas”, Miss Anna Maria writes, “was a sea captain. There are many stories told of him concerning his life at sea and one bears special mention. During the war of 1812, between the English and the French, William Thomas was employed by the former nation in carrying stores for the navy in the West Indies. During one of the bombardments his ship was loaded with shot, shell, and powder for the fleet. He arrived just as the bombardment commenced, and the Admiral ordered him to the stern of the Flagship, and during the whole of the fight he swung from her fastened by a hawser. The French made a brave resistance, and hoping to set the ships of the English on fire, they heated the shot until it was red-hot and then fired it at the English. William Thomas, though not involved in the fight, was placed in charge of a dangerous task. A large crew who was placed at his command, saw to it that their fleet of ships had the decks flooded with water and covered with wet blankets. If a shot struck, the crew removed it with tongs and hurled it hissing into the sea. Fortunately no ships were lost or even damaged. The crew was probably paid well for this dangerous expedition.”

Captain William Thomas Outerbridge married his second cousin, Elizabeth Outerbridge, from ‘The Locusts’, another family home on Fractious Street. There is a romantic tale told by Miss Anna Maria about Elizabeth, which is both sad and beautiful. It is recorded thusly: “Grandfather’s first wife, Elizabeth, who was a pretty young girl, the daughter of William Outerbridge, a planter from ‘The Locust’, is said to have always been delicate. Shortly after her marriage, she was taken ill, which illness terminated in consumption. Thus during all of her short married life she was more or less an invalid. For several years before her death she only left her bed for a sofa or chair propped up with pillow. When she was first married her husband brought her a fine saddle horse from Virginia, and on fine days, she would ride about on this for an hour or so. When she was taken ill, her servant, Beck, would ride the horse until it was tired enough to go very quietly. Elizabeth’s room was built so that the lower storey was used as a bedroom for two slave girls, and at any time of the night the tinkle of Elizabeth’s bell would bring one or both girls to her bedside. As Elizabeth’s husband was at sea almost continuously during this period of his life, she must have been very lonely. However, she was passionately attached to her husband, and when he was at home from sea she was never happy unless he was by her side. Shortly before her death she asked her husband to have her buried in the garden, just under the dining-room window at ‘Cedar Grove’ so that he would not forget her. Unreasonable as this might seem, Elizabeth’s wishes were carried out and her grave was made in the lawn to the north of the house; and until his death, William Thomas always had beautiful flowers planted around Elizabeth’s grave.”

Elizabeth Outerbridge died on 2nd May, 1806. She left one child, a daughter, named Elizabeth Wilkinson Outerbridge, who married Captain Lawrence Nesbit Hollis of Bailey’s Bay in 1809. Captain Hollis is remembered as the sailing master of the man-of-war ship, The Bermudian.

In the summer of 1808, William Thomas Outerbridge married his second wife, Anne Albouy Wilkinson. He was forty-four, she was twenty-two. Miss Anna Maria describes her as “a dark brunette with bright colour in her cheeks and lips, and having expressive, brown eyes and a fine figure. She was also exceedingly clever and precise in manner and dress having studied with her sisters under Mrs Hoffman, one time a lady-in-waiting to Princess Caroline Matilda, the unfortunate sister of King George III.”

William Thomas and Anne Outerbridge had nine children, the eldest being Dr. Thaddeus who was Miss Anna Maria’s father. Anne (Wilkinson) Outerbridge was the daughter of William Wilkinson, ‘Gentleman of Devonshire Parish’, whose family settled in Bailey’s Bay about 1810, and came to build and own the houses and properties along Wilkinson Avenue. William Wilkinson’s wife was Susannah Steed, whose family had come from France. Susannah’s brother, Bobby Steed, had owned property on Wilkinson Avenue, where the Lyceum is now, so this may explain how the Wilkinsons came to live in Bailey’s Bay. Miss Anna Maria describes William Wilkinson as “a tall, handsome man, dignified and courtly with clear, blue eyes.” He was a member of the Assembly for some years and had both maritime and farming interests.

William Wilkinson’s wife Susannah, died in 1796 at the age of twenty-nine. She had married at eighteen, gave her husband ten children, got pneumonia and died before her eldest child was eleven. Six of the children survived and Mr Wilkinson brought them up himself. He never remarried.

Look out for parts two and three of Life in Old Bailey’s Bay in the coming weeks.