The name is derived from the nautical term "the roads", a place less sheltered than a harbour but which ships can easily get to. A area called Wickhams Cay was reclaimed from the sea and is the centre of tourism. The oldest building in Road Town, the old HM Prison on Main Street, dates from the 1840s.

The town is one of the principal centres for bareboating (self-hire yacht chartering) in the Caribbean. Road Town is the headquarters of Tortola Marine Management, located in the Road Reef Marina, and The Moorings, which are two of the main charter boat companies operating out of Road Town/Road Harbor.

Geographical limits

There is some ambiguity as to the precise geographical extent of Road Town. Approaching the town from the west, a sign at the bottom of Slaney Hill greets visitors to Road Town. But traditionalists assert that the town itself only starts from Road Reef and Fort Burt, and that Prospect Reef Hotel (which covers almost all the land in between) is not technically in Road Town.

Approaching Road Town from the east, there is similar ambiguity if Road Town begins at the Port Purcell roundabout below Fort George, or whether it also includes Baughers' Bay.

Fort Burt and Fort George were the historical markers of the western and eastern limits of the town which benefitted from the protection of the Crown.

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