Before the removal of the garrison in 1854, the Royal Gaol had been in downtown Scarborough, in a cramped stone building best suited for about 20 persons but accommodating 50, both male and female.
The roof leaked badly and the Superintendent, Kaye Rowland, was at great pains to best care for the inmates. With the garrison gone in 1854, it was decided to move the gaol to Fort George, in the buildings occupied formerly as barracks. The Public Works Department undertook hasty renovations and the move was effected. It was described in 1866 as follows:
"While the colony was under the rule of Governor Shortland, an act was passed to convert the military prison and cells at Fort King George into a convict prison; and Mr Keens, while he administered the government, sought to render the buildings at the Fort more available for the public service by converting the military hospital there into a common gaol, by which accommodation might be provided for all classes of prisoners under one establishment.
"But it was reserved for Mr Drysdale's Government to mature this very excellent arrangement, by which all persons suffering imprisonment were removed from the confined and unhealthy prison at Scarborough to the airy and capacious buildings at Fort King George, where classification, so necessary to discipline and good order, could be well perfected, and imprisonment be rendered a punishment.
"The prisoners were also indebted to Governor Drysdale in providing them with the means of religious consolation: under his management a chaplain of the jail was for the first time appointed, and this pastoral care is still afforded to inmates of the prison, indeed it may be considered permanent."
The gaol received regular visits from the District Medical Officer who both resided and practiced at the military hospital in Fort George as well as from a minister of St Andrew's Anglican Church, which formed the chaplaincy of the prison.
In 1877 the prison had its greatest intake, comprising almost the entire village of Roxborough. The manager of the estate was attacked and apparently killed for he was chased into the high woods and never seen again. The estate house was burnt down.
As unrest spread, the five policemen in the village, led by Cpls Belmanna and Reid, came to the fore. A scuffle ensued between the police and rioters, and allegedly, a civilian was shot. This was the spark to the powder keg and the police fled and barricaded themselves in the station (still in the same location atop a hill today). The crowd surrounded the building, threatening to burn it with all inside if Belmanna was not handed over. A small band of militia from Scarborough arrived on the scene, but was repulsed, sending them packing back with the news to authorities that a very serious threat was at hand. Belmanna had been seized by the insurrectionists. He was beaten badly and mutilated. A woman, called Ti Piggi (because of her porcine appearance) was said to have gouged out Belmanna's eyes and then stabbed him fatally. The other four policemen in the station were also brought out to face the wrath of the mob. All were beaten, stripped and humiliated.
For a week, the rioters held sway until a warship hove into sight. Its captain, Adams, realised that the risk to a landing party of marines would be too great, nor was he inclined to wholesale slaughter of the rioters by shelling the village with the great cannons of the ship. Using great tact, Captain Adams sent a boat ashore with an emissary, who thanked the rioters for 'keeping the peace' and not destroying public property. He invited the mob aboard to be decorated for their service. The rioters fell for the ploy and went aboard by the dozen. When he was satisfied that the ship could hold no more, the insurrectionists were clapped in irons and taken to Scarborough to stand trial. Many were exiled for life and others were sentenced to life in prison. As a result, the colonial authorities realised that Tobago, weakened by recession and unrest, had to be allied to another colony. This led to the political annexation of Trinidad and Tobago in 1889.
Prisoners from Tobago were sent thus to Carrera Island in Trinidad, reducing overcrowding at Fort George. The gaol remained at Fort George until the large and extensive police complex at Bacolet was erected in the 1950s. There, a fairly ample prison block was constructed and since the long-term prisoners were sent to Golden Grove in Trinidad, the Scarborough Jail was closed, ending an existence of almost a century. Today the buildings have been restored as part of the Fort George historical complex.