Sailing craft date back to the Taino and Arawak peoples who inhabited Anguilla before the British Colonisation.
An Anguillian defense force was led by Lieutenant Governor Benjamin Gumbs, and for the next four days they were beaten back through the capital of The Valley and onto Sandy Hill, where they fortified themselves in a former Dutch Fort.
Desperate for ammunition, they were said to have used lead weights from fishing nets and musket shot, and an Anguillian sailing ship was sent to St. Kitts to request aid.
Barton acted swiftly to relieve Anguilla, and the Lapwing's presence drove the French to attempt to retreat.
They surrendered to the Anguillian forces, were imprisoned and then massacred in retaliation for the massive amount of damage inflicted by the invaders.
However, the main effect was a result of the devastation inflicted on the plantations, in addition to the island's naturally arid climate and hurricanes doomed large scale agricultural efforts.
[1] After the American Revolution the Navigation Acts banned trade between the new United States of America and the British West Indian colonies.
These ships exported Canadian timber and fish and were then reloaded with West Indian sugar, rum, molasses and salt.
Beginning in 1860, American entrepreneurs invested in several pieces of equipment and construction on the island, including a steam railway, accommodation for workers from Anguilla, a rock crusher and several loading points for ships.
Foreign exchange earnings allowed the purchase of metal pieces for use on ships, such as hawse-pipes and deck pumps.
By the end of the 19th century, an impressive number of the roughly 4,000 residents of Anguilla owned a trading sloop or schooner.
Large plantations recruited cane cutters from Eastern Caribbean islands - Particularly, St. Martin, Tortola, Anguilla, St. Kitts and Antigua.
The Anguillian trading fleet found it an even greater opportunity - Many of the labourers from islands in the southern end of the archipelago came to St. Martin to find transportation to Santo Domingo.
In addition, the exchange also opened up new trade routes between the Eastern Caribbean and Puerto Rico and the Dominican Republic.
The return trip in July, being a beat directly to windward, was difficult and long, taking up to twenty-one days.
Some even breached international navigation rules and switched their starboard and port lights in attempt to fool their opponents.
In addition, as most of the able-bodied men were employed as either mariners or cane cutters, the elderly, women and children highly anticipated the return of the schooners.
On the event of the top of a mast being spotted, eager loved ones on shore would watch anxiously as two or three ships would fight for first anchorage.
The Warspite, which continued sailing decades later under various captains, was later commemorated as a symbol of Anguilla and featured on the EC ten dollar bill.
Surplus fish were sold in St. Martin to support the purchase of foods such as flour, rice, cornmeal and salt pork, which were unavailable in Anguilla otherwise.
Usual catches included grouper, butterfish, goatfish, grunt, snapper, oldwife and hammerheads (a blue fish which is now rarely seen).
As refrigeration was unavailable at the time, boats were required to reach shore before midday to sell their catch quickly.
As a result of living off of mainly fishing and subsistence farming, Anguillians had little money to hire labor for plowing, or "holing ground" as it was locally called.
The ideal smuggling boat would be able to sail across the channel from St. Martin laden with cargo and arrive in Anguilla well before dawn.
Alternatively, one captain may decide to "draw" and either tack earlier or change his point of sail to avoid the manoeuvre.
Throughout the English-speaking Caribbean the first Monday in August is a national holiday commemorating the Emancipation Act passed by the British House of Commons on July 31, 1833.
A few days prior, the schooner Betsy or the sloops Speed would sail to St. Kitts for supplies including ice packed in sawdust.
West End, Island Harbour, Sandy Ground and Blowing Point would hold their own races with little organization and no prizes.
The first organized regatta on August Monday can be credited to good friends Melrose MacArthur Owen and William Elliot Carty, both residents of North Hill.
The son of Herbert Owen (a principle Sombrero lighthouse keeper), he was employed at "The Factory" (a general store, small cotton gin and blacksmith's shop), he often experimented with plumbing, electricity and machines at a time when such objects were rare in Anguilla.