Across from the downtown ferry jetty is the Sir Olva Georges Plaza, named for the first British Virgin Islander to be knighted by the queen. Sir Olva lived on Main Street in a home that has now been converted into a trendy restaurant. Before reclamation changed the shoreline, Sir Olva Georges Plaza served as the main jetty and market square for Tortola. During slavery, it was the site of slave auctions. After emancipation, the square retained its prominence as a center for trade and commerce. A 1920s visitor described the weekly market held there:

The sellers mostly squatted on the ground with their produce in front of them in calabashes, in trays, or displayed on old sacking. Everyone appeared radiant as the sun and the sea, exchanging greetings of the market-place, chattering and gesticulating whether anyone attended or no.… A row of brown sloops from the islands lay moored alongside the white glare of the wharf, their sails furled, lazily rocking in the blue-lit waters.

Today, the plaza is a quiet place to sit, rest, and watch the comings and goings of Road Town life. It comes to life for occasional events and performances, especially at Christmastime.

Across Main Street from Sir Olva Georges Plaza is the Old Administration Building, which today houses the Road Town Post Office and several other government offices. It was from this building that the British Virgin Islands were administered for many years, until the mammoth Central Administration Building was completed in 1993 and most offices moved there.