The area was settled in the 1760s by New England Planters following the Acadian Expulsion. The town was formally founded by Loyalists in 1783 (the year that the Treaty of Paris was signed to end the American Revolution). Current-day Weymouth was once called Weymouth Bridge, and Weymouth North was called Weymouth. Weymouth is supposed to have been named in honour of the previous settlement of the Strickland family from Weymouth, Massachusetts.
Shipping and shipbuilding were the main industry in the mid-19th century. Remnants of docks can be seen on the Northeast side of the Sissiboo today. Goods such as lumber were loaded on ships at these docks and shipped all over the world. Until recently, Weymouth housed the oldest general store in Eastern Canada. Opened in 1837, the store was called The Trading Post, but closed in 2009. The village also houses one of the original offices of the Merchants Bank of Halifax (later renamed Royal Bank of Canada). This building is now part of the aforementioned Weymouth Trading Post building. The Dominion Atlantic Railway stopped running through Weymouth in March 1990.
On 4 August 1909, 2 churches, a hotel, and several other buildings were destroyed due to a fire. On 2 October 1929 a fire started in the general store of Captain R.D. Barkhouse and swept through the downtown area destroying 25 buildings including retail shops, factories and private homes. It was estimated that the fire caused approximately $250,000 in structural damage. No serious injuries or deaths occurred because of the fire. On 6 February 1958, another fire destroyed the boat and furniture plants of Weymouth Industries Ltd., and in June 1959 six businesses were wiped out due to fire.
The Sissiboo River overflowed in March 2003, flooding the town under almost two feet of water.
New France ("Electric City")
The lumber community of New France, located about inland from Weymouth, was founded by the Stehelin family who came to the area from Normandy, France in 1892. The community they established was notable for its early use of hydroelectric power generation, earning it the local nickname "The Electric City". Also notable was the Stehelin family's railroad, the Weymouth and New France Railway, constructed using logs as tracks, which they used to bring lumber to the company wharf at Weymouth. As many as 1.5 million board feet of timber were shipped annually from New France to South America and England. The railway was destroyed by fire in 1907 and the business ceased not long afterwards. There is little left of New France except for the foundations of the city buildings. J.D. Irving, recent owners of the land, established walking trails and interpretive signs at the site and fixed the foundations so they are safe for visitors to explore. The lands were purchased by the Province of Nova Scotia in 2010, thus assuring the protection of this unusual part of the province.