The British discovered Barbados many years after the Spanish, whose only interest in this seemingly inconsequential plot of land was to give it a name. They called it 'Los Barbados' (the bearded ones) for the trees that were plentiful in the mangroves and grew  roots from their branches. These trees today are called bearded fig trees.

In 1625, Holetown was the site of the first English settlement of Barbados. The envoy (led by John Powell) was blown off-course from South America to England and took the opportunity to claim the island for the Kingdom of England. Some personal possessions were left behind and the crew departed Holetown for England.

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On 17 February 1627 the brother of Captain John Powell (Captain Henry Powell) aboard the "Olive Blossom" returned with his benefactor, Sir William Courteen, a Dutch-born English merchant trader, and fifty other shareholder settlers. 

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The name Holetown comes from the stream, The Hole, which provided a safe landing place for the settlers. Also sometimes called Saint James Town, the settlement was, until 1629, the island's only town. Holetown celebrates the founding of the first five plantations in Barbados, the first major fortification, the first place of Justice, and the first Governor's House.

After Lord Carlisle gained control of Barbados as a protectorate of The Crown, he decided to found his own settlement in the southern part of the island. Carlisle's move gave way to Bridgetown being settled along Carlisle Bay and a shift of the capital for the island to that location.

The Island's oldest church, St. James Parish Church, was erected here in 1628, a year after the first settlers landed.