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Early in the life of the colony, the Government offered grants of land and convict labour to open up and settle areas beyond the existing settlement boundaries. The Australian Agriculture Company, formed in England in 1824 with $1M capital, took up a grant of 1,000,000 acres of land extending from Port Stephens to the Manning River. Chief Agent for the Company, Robert Dawson, established Headquarters at Carrington, Port Stephens in early 1826 and explored up the Karuah River Valley, naming places as he travelled. He continued to follow the valley north, arriving where Gloucester now stands in November 1826. As the land appeared ideal for grazing and agriculture, early settlement was encouraged.Later, an 'outstation' at Gloucester was established where "The Homestead" is located today.
The early pioneers were stockmen, shepherds and woodcutters who settled along the riverbanks. The Gloucester township site was laid out by the Australian Agricultural Company in 1855 but development was slow. The location of the town was well chosen with pleasant views of rolling hills and valley vistas in all directions. The first Anglican Church was built by the Company in 1860 and serviced by the Minister from Stroud. Gloucester's population in 1866 was 30 persons. By the end of the Century the Australian Agricultural Company began to sell off land. A development company, Gloucester Estate Limited, purchased land in the Gloucester area for twelve shillings and sixpence per acre. Subdivision and good promotion by Gloucester Estate resulted in rapid growth with land selling at between twenty shillings and five pounds an acre by the end of 1903.
In 1905 a School of Arts was built and the Gloucester Advocate newspaper was established. The Gloucester Shire Council first met in 1906 and built the First Council Chamber in Church Street in 1909. This building is now the Gloucester District Historical Society's Folk Museum. In the same year a butter factory was established. Within a decade since its establishment, the village had developed from a sparse and scattered settlement into a prosperous and growing township. Many fine Federation period buildings can still be seen in the town today. In 1913, with the town population was estimated at 900, the Railway arrived from Newcastle and Sydney. This remains the main north coast line from Sydney to Brisbane.
Today, Gloucester Shire covers 3,000 square kilometres and boasts a population of 5,000, with 2600 living within the township. Altitude of the township is 100 metres above sea level, with an average annual rainfall of 985 mm. Major industries are in agriculture - traditionally in beef and dairying, with more "boutique" industries such as aqua-culture, olive groves, vineyards and wineries, specialist nuts now established. There is a coal mine at Stratford, and whilst the timber industry has been declining, there are still a number of timber mills. Tourism is a growing industry, which assists in the sustainability of the township while it undergoes the transition from the more traditional industries. The major attraction for Gloucester is its proximity to the World Heritage Barrington Tops as well as nature based activities such as horse riding, kayaking and bush walking.