Deed references suggest British settlement in Bridgetown from the early 1760s onward, after the Acadians were expelled from Nova Scotia in 1755.

The community grew into a successful wooden shipbuilding area during the 19th century, accounting for many grand homes.

The town was actually an entrepot for the agricultural and forest products of the surrounding areas and became a significant manufacturing and commercial centre in the 19th century.

Captain John Crosskill, who owned or controlled the central part of the community, what is now downtown, divided the bulk of the lands into 90 by 90 lots in 1821.

The more romantic has it that the community was named after Bridgetown, Barbados, because Captain Crosskill had once been stationed there, and had apparently much enjoyed it.

A brick plant, soda pop factory, and various apple warehouses were built along the railway in this area.

CN had a passenger station as well as a small yard on the north bank of the river, serving various apple warehouses and the Acadian Distillery factory.

Black people have a long history in Bridgetown, residing primarily in the areas of Inglewood Road, "The Pasture" and "The Tracks".

[5] The Morse-Magwood House was built in 1871 and is noted as a fine example of Second Empire architecture and is considered one of the most picturesque homes in the province.

[13] The historic downtown fronting Queen Street underwent redevelopment and beautification during the 1980s as a result of federal grants.

[15] In 2011, the town council drew national headlines by resigning en masse over financial difficulties including a misappropriation of funds by a municipal employee who was later convicted.

[16] A subsequent provincial audit found that $113,195.96 had been misappropriated from the town over 5 years by one employee, and additional losses were incurred from related costs and record-keeping errors.

The council cited ongoing financial pressures in the form of increased costs to provide services and pension obligations, as well as declining revenue from the town's property tax base.