Holetown exists because of a wrong turn. In 1625, Captain John Powell was sailing from South America back to England when winds pushed his ship toward an island the English had not yet claimed. Powell went ashore, planted a flag for the Kingdom of England, left some personal possessions behind, and departed. Two years later, on February 17, 1627, his brother Captain Henry Powell returned aboard the Olive Blossom with a more deliberate purpose: settlement. He brought Sir William Courteen, a Dutch-born English merchant who financed the venture, along with fifty shareholder settlers and ten enslaved Africans. They landed near a stream called The Hole, which offered a protected approach from the sea. The name stuck, and Holetown became the first English settlement on the island.

For a brief window, Holetown was Barbados. Until 1629, it was the island's only town, and it accumulated firsts the way young settlements do: the first five plantations, the first major fortification, the first place of justice, the first Governor's House. St. James Parish Church, the oldest church on the island, was erected here in 1628, just a year after the settlers arrived. Holetown also anchored Barbados's early transatlantic trade, shipping goods to Bristol, London, and illegally to Boston. But the town's primacy was short-lived. When Lord Carlisle gained control of Barbados as a protectorate of the Crown, he founded his own settlement to the south along Carlisle Bay. Bridgetown grew, became the capital, and Holetown settled into the quieter role it holds today.

What the English built at Holetown was the seed of Barbados's plantation economy. Those first five plantations would multiply across the island, and by the mid-1600s Barbados was producing more sugar than any other English colony. The wealth was enormous, the labor that produced it forced. Enslaved Africans, brought to the island in numbers that would eventually dwarf the settler population, cleared the land, planted the cane, and worked the mills. The ten captive people who arrived with Henry Powell in 1627 were the first of hundreds of thousands. Holetown's founding is inseparable from this history. The settlement that began with fifty shareholders and a merchant's ambition became the entry point for a system of exploitation that defined the Caribbean for centuries.

Today Holetown is a small city on Barbados's sheltered west coast, part of the parish of Saint James. Since 1977, the annual Holetown Festival has commemorated the 1627 landing, drawing visitors to a place that trades more on its beaches and restaurants than its historical weight. The erroneous monument still stands. McGill University operates its Bellairs Research Institute here, conducting marine and environmental research in the Caribbean. The town has been twinned with the London Borough of Haringey since 2009, a connection that links two communities separated by the same Atlantic that once carried ships between them. Holetown is quiet now, a place where the drama of first contact and colonial ambition has been absorbed into the landscape. But the stream called The Hole, the landing site, the wrong date on the monument, all of it points back to a moment when the English stepped ashore and set something irreversible in motion.