Home Massachusetts John Aylett, The Royalist Adventurer Who Owned a Boston Tavern

John Aylett, The Royalist Adventurer Who Owned a Boston Tavern

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Capt. John Aylett, an English nobleman, launched his career on the high seas in Boston after he fled his native country to escape persecution. Unlike the Puritans who arrived a decade earlier, he wasn’t escaping royal restrictions on religious practices. In fact, he was escaping the Puritans who had executed the king.

Capt. Aylett was a Cavalier who had an illustrious military career as a Royalist during the English Civil War. He then founded the prominent Aylett family of Northern Virginia before his life ended aboard a pirate ship.

John Aylett

Capt. John Aylett was born around 1627 in Magdalen Laver, Essex, England. He came from a distinguished family originally named Ayloffe.

He was the youngest son of Sir Benjamin Ayloffe, 2nd Baronet and High Sheriff of Essex County. His grandfather, Sir William Ayloffe of Great Braxted in Essex, was knighted by King James I in 1603 and became a baron in 1612. Both he and Sir Benjamin were Members of Parliament.

The family was staunchly Royalist. John’s father, Sir Benjamin, was imprisoned for five years in the Tower of London and his lands seized for his support of King Charles I. Paying a 3,000-pound fine enabled him to escape a death sentence but also impoverished him because Parliament sequestered his estates. With the restoration of the monarchy, Sir Benjamin become a Knight of the Shire in Essex.


Capt. John Aylett belonged to the supporters of King Charles called Cavaliers—men in royal armies who owned rural estates. A chaplain to the king once described them as gentlemen “well borne and bred, that loves his king for conscience sake, of a clearer countenance, and bolder look than other men, because of a more loyal Heart.”

Capt. John Aylett, at only 19, was admired for his role defending the city of Colchester during the Parliamentarian siege in the summer of 1648. Sir John Bernard Burke (a British genealogist who helped publish Burke’s Peerage) referred to him as the “gallant” Capt. Aylett “so distinguished in the cause of King Charles during the great civil war.” Burke noted he had fought in many engagements in the war.


During the battle for Colchester, Capt. John Aylett and five other leaders wrote a letter to Parliamentarian forces at Cattaway Bridge nearby on June 22, 1648. “We are commanded by Sir Charles Lucas, Commander in Chief of His Majesty’s Forces in Essex, to desire your Positive Answer, whether you do declare yours selves to be our Enemies or no?” The letter by “we Essex Men” asked for the return of their captured soldiers, their horses and arms and sought to avoid bloodshed.

However, Parliamentarian soldiers continued to attack the Royalists. After a fierce battle outside Colchester, the Royalists retreated inside the city walls. By August, all the food inside the city had run out. His starving soldiers were reduced to eating cats and dogs, so Aylett fed them the 100 horses he had bought for the cavalry.

The city fell to its enemies on Aug. 27, 1648. They captured Aylett and the other leaders and sentenced them to be shot. Before being taken to London for a formal trial, Aylett managed to escape, dressed as a woman, before being captured sometime later. (Only one other Royalist commander, Col. Henry Farre, escaped execution—by hiding inside an oven before Parliamentarian soldiers could find him. Farre then fled and went into hiding until 1659.)

The Siege of Colchester


The Cavalier leaders under whom Aylett served were put to death for taking up arms against Parliament. But why not Aylett? A 1910 book on ancestral records by the Colonial Dames of America provided the answer. Oliver Cromwell, who had seized power, pardoned Capt. John Aylett due to the mitigating circumstance of his youth. Aylett then paid a fine of 460 pounds for his life and freedom.

During the English Civil War, Parliament formed the Committee for Compounding with Delinquents (Royalists). Compounding, a legal procedure, allowed some Royalists to avoid prosecution by paying a fine if they had sufficient wealth and vowing they would not support the king.

Sealed Knot

As a reward for Aylett’s loyalty, the deposed king, Charles I, added the rose of England to his coat of arms, having ‘no other reward to bestow upon him.’

Three years later, the Parliamentarians executed Charles.

Capt. John Aylett took part in other battles as a member of the Sealed Knot secret society, dedicated to restoring the monarchy. Although King Charles II was in exile in Paris, he commissioned this group to coordinate uprisings and his return to power. During this time, Charles appointed Capt. John Aylett to be governor of Chepstow Castle in Wales. Aylett, though, returned to England after he was betrayed. He fought on the losing side in the Battle of Worcester in 1651 before fleeing with other Cavaliers to safety in colonial America.

Boston and Virginia

Capt. John Aylett made Boston his new home. He became a merchant and bought land near the waterfront. He struck up a friendship with master shipbuilder Capt. Thomas Hawkins, who had relocated to Boston from London. Hawkins bought land and built a house that became the famous Ship Tavern (also called Noah’s Ark) on the corner of North and Clark streets until 1866.

Hawkins died at sea in 1654 during the maiden voyage of a 400-ton vessel he built called the Seafort. Aylett married Hawkins’ daughter, Mary Hawkins, that year, in a ceremony performed by Capt. Humphrey Atherton, later a major general. Through his marriage, Aylett inherited the famous tavern.

Married life didn’t keep Capt. John Aylett from sailing to England to join some 300 Royalists in the failed Penruddock Uprising of 1655. The Royalists fled after a quick defeat. Capt. John Aylett then moved to Virginia—the American colony most loyal to King Charles II. He established his family in the Northern Neck in 1656 in the present King William County. A community there continues to bear the family name Aylett.

The High Seas

Having learned about ships in Boston, Capt. John Aylett took to the high seas under Cromwell’s reign. He became the co-owner of the ketch called Providence.

During a voyage from New England to Jamaica, a Spanish privateer seized the vessel with Capt. John Aylett aboard. During his year of captivity, Capt. John Aylett smuggled a letter to Cromwell in England. Contained among a collection of state papers in 1656, the letter provided intelligence that helped defeat a Spanish insurrection against the British, who controlled the island.

Somehow Capt. John Aylett gained his freedom. He naturally found favor with King Charles II after his return to the throne in 1660. He served as a commander in the King’s Royal Navy, then engaged in hostilities with the Dutch, the Spanish and pirates.

The Calendar of State Papers under the reign of Charles II record Aylett’s activities in the Royal Navy for the next decade. During this time, he apparently married a woman in Virginia, where they had a son, Philip Aylett.

From 1658 to 1660, he commanded the HMS Coventry, a 28-gun ship taken in 1658 from the Spanish. At the time, the English encouraged pirates to operate from Port Royal, Jamaica, and attack Spanish ships. Capt. John Aylett patrolled the seas from there.

From 1664-65, he commanded the HMS John and Katherine, a 32-gun vessel with 150 men. He was promoted in 1665 to command the HMS Portland, a 40-gun fourth-rate frigate. During the Anglo-Dutch War, he fought in the epic Battle of Lowestoft.

The Battle of Lowestoft

Grievous Mortification

During another naval incident with the Dutch, an English ship crashed into the HMS Portland. A Royal Navy historian called the incident “a grievous mortification to this gallant man, and equally unfortunate to his country, to be deprived of his services just at the moment when they were so much wanted.”

Disillusioned, Capt. John Aylett quit the command of the Portland after taking the blame for its damages in 1667. He then petitioned King Charles II to grant him a seized prize, a 60-ton ship called the Casamine, moored in southeast London. Aylett reminded the king of his faithful service and that his father, Sir Benjamin, suffered financial ruin by supporting Charles I.

The King, however, appointed Aylett to command the HMS Forrester in 1668. He left that post, however, possibly retiring from service. A year later, he commanded his own 50-ton frigate, the Lilly, as a privateer for England. It had 10 guns and 50 men.

Capt. John Aylett then operated out of Jamaica, an infamous pirate haven. He formed an alliance with notorious privateer Capt. Henry Morgan.

In January 1669, ship captains held a war council meeting aboard Morgan’s ship, the Oxford. They gathered to discuss attacking Cartagena, a major port of the Spanish Main on the north coast of Colombia.


Henry Morgan

Death and Descendants of John Aylett

While the pirate captains and privateer commanders dined on the quarterdeck of Morgan’s ship, an explosion rocked the vessel. A main mast fell on Capt. John Aylett, who died along with 200 others, including four captains. Afterwards the Lilly frigate joined Capt. Morgan’s fleet.

The Aylett family in Virginia preserved Capt. John Aylett’s memory with pride. They became notable American patriots who fought against the English crown during the Revolutionary War, even serving in the Continental Congress. Some Aylett family members married into the families of George Washington, Patrick Henry and Robert E. Lee.

The author of this story, Noël-Marie Fletcher, is a journalist and a descendant of Capt. John Aylett through her great-grandmother Elizabeth Aylett Gibbons, a member of the Virginia Aylett family.

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