Founded in 1729 after the death of John Wolmer who left in his will £2,300 from his estate to start a "Free School" in his parish, Wolmer's started with an enrollment of 500 boys.

Wolmer's school has had several locations in the parish of Kingston. It began in the house of Samuel Turpin on land between Port Royal Street and Harbour Street, in 1736. Turpin had left in his will of 1734 to Wolmer's the annual rent of his house on that lot of land. The school was called ˜Wolmer's Free School at the time.

In 1742 the Trust bought six lots of land on Duke Street, from Samuel Clarke for £93. Two buildings were constructed for a classroom and lodging for the headmaster and boys on the lot. Mr. John Conron was paid £250 for construction. The school was moved from Harbour Street to the new location at upper Duke Street sometime about 1742.

When the headmaster Michael Mill died in 1755, the school was closed for two years, until 1757. The Governor of Jamaica, General Knowles, had the building leased to the government as a storage for public records. It was also used as a courthouse for the county of Surrey, so when classes resumed in 1757, the school was moved to rented premises at Parade and remained there until 1777.

In 1777, Wolmer's was moved to Church Street when the house of a Mr. Bullock was leased for the sum of £120 per annum, for three years. In 1783, it was bought for £900. The Duke Street property had been sold at a public auction for £800 in 1780.

More land was bought in 1794 to the north of the school for £250 and fenced in by a brick wall. In 1807, the two northernmost lots of land of the school property was sold to the city of Kingston for the construction of a Poor House. Wolmer's was briefly housed in the Poor House (1811), while extensive repairs were carried out, but the inmates objected. Between October 1811 and August 1812, Wolmer's occupied the Coke Chapel on East Parade while the school was enlarged. Rent of £85 was paid to Coke Chapel for the time the school was there.

When an earthquake struck Kingston on January 14, 1907, the school suffered major damage but was not destroyed. Minor repairs were carried out and Wolmer's continued at Church Street between 1907 and 1909. A decision was made to find a more suitable site however, as the school had outgrown that location. In 1908 the lands at Quebec Lodge was acquired to house the Boys' and Girls' Schools. Quebec Lodge was the site of the Jamaica Exhibition of 1891, located north of Race Course (later called George VI Memorial Park and now National Heroes Park) and is the present site of Wolmer's Boys' School and Wolmer's Girls' School. Wolmer's opened at its present site in January 1909.