The long, low Old Customs House, home to several boutiques and a plant store, marks the division between Lower Main Street and Upper Main Street, where the street makes a sharp left turn and heads farther inland. The corner is known locally as Fonseca Corner, named after a prominent Road Town family that lived there.

The picturesque St. George’s Anglican Church (170 Main St., 284/493-3894) is one of the oldest houses of worship on Tortola. All the early church records were lost in 1819 when a hurricane destroyed the building. Following emancipation, the church served as a school and community center for the residents of Road Town.

A few steps farther up Main Street is the Road Town Methodist Church (186 Main St., 284/494-2198) centerpiece of the other long-standing denomination of the British Virgin Islands. The first Methodist missionary came to Tortola in 1789 and quickly converted thousands of slaves to the faith. In 1796, the church had 3,168 members in the British Virgins, more than any other Methodist mission in the West Indies. It remains the single largest denomination in the BVI. Today’s Road Town Methodist Church was built in 1926 after the original structure was destroyed by hurricane in 1924.

Sandwiched between the two churches is the Old Prison, with high white walls and a broad red door. The prison was in use continuously from the late 17th century until the mid-1990s, when a new prison, financed by the British government, opened on Tortola’s remote northeastern corner. For a brief period in the early 2000s, the old prison was put to use again to ease overcrowding at the main facility. It is now empty once more.

Across Main Street from the Methodist church is a large, pink concrete structure known as The Fireproof Building. The building got its name in 1853 when it was one of the only buildings to remain standing after rioters set fire to Road Town in protest of an increase in the cattle tax. The unrest eventually spread throughout the countryside as residents set fire to many of the remaining plantations and estate homes.

It was near here that hangings took place in the territory, the most famous of which occurred in 1811 when Arthur Hodge, a wealthy planter, was hanged for the murder of his slave. The last execution to take place here is a distant memory, and in 1999 the U.K. government forced the territory to take capital punishment off its books—which it did, but over loud local protests.