San Fernando was founded in 1786 as a town, initially in the area of St Vincent Street and Chacon Street. It was founded on the site of an old Indian mission dating from 1687. The last Spanish Governor, Don Jos� Maria Chacon laid out the town himself.
A fire destroyed the old town in 1818 but rebuilding was swift. By the 1820s it was creeping southwards, uphill towards the Gomez family's Paradise sugar estate. In 1846 San Fernando became a municipality, being elevated to borough status in 1851. Shortly before this time a narrow unpaved dirt track leading from the sugar-belt Naparimas, became a focal point for commerce.
Gradually, the thoroughfare developed and became known as High Street. It was a chaotic place at best, with pedestrians vying for space with carts rattling in with hogsheads of sugar, bound for King's Wharf, whence they would be shipped.
At the western end of High Street was the Cipero tramroad line, Trinidad's first railway, which had been founded in the years 1847-49 by William Eccles. There was also an Anglican church here, with a cemetery which was moved to Harris Promenade in 1872, the land being sold to finance the new church building.
In 1882, a devastating fire razed High Street, but it was rebuilt in a more aesthetically pleasing style, like a western town, with wooden piazzas. A couple of public buildings were here too, although these were later moved to make way for stores. The fire inspired the formation of a volunteer fire brigade, which existed from 1886 until 1954, when it was taken over by the T&T Fire Service.
A description of High Street and the brigade in 1887 runs thus: "High Street, the chief business thoroughfare, contains a number of well-arranged, amply-stocked stores. The principal public offices are here; those of the sub-receiver (Mr LG Hay), warden (Mr JL O'Connor), and post-master (Mr J C Lewis). Many of these are of new and modern appearance, for in 1883 the town was unfortunately, or fortunately (who knows?), visited by a ravaging fire, which made a clean sweep of some of the mercantile houses.
The San Fernandians, however, were not to be daunted by such a commonplace occurrence, and ere long the present structures arose phoenix-like out of the ashes. It was this fire which led to the formation of the town Volunteer Fire Brigade, an organisation now in a thoroughly efficient state, having an engine and hose, with the necessary fittings and appliances, to enable it at all times to turn out for immediate action."
High Street was paved with asphalt in the 1890s, replacing the dusty gravel surface.Today, it remains the chief business centre of San Fernando and is to that city what Frederick Street is to Port-of-Spain.Its notoriously hilly nature means that a walk to the east is quite a physical undertaking, since the pavements are stepped and are often congested, forcing pedestrians to walk on the roadway.