Louis-Alexandre des Friches de Meneval landed at Chedabouctou in 1687 when arriving to take up his position as governor of Acadia.

Claude Bergier led other merchants from La Rochelle, France in enjoying a fishing monopoly in Acadia.

In 1682, Fort St. Louis was established by the Company of Acadia (Compagnie de la Peche Sedentaire) to protect the fishery.

[5] During King William's War, in 1690, Captain Cyprian Southack proceeded to Chedabucto to take Fort St. Louis which, unlike Port Royal, Nova Scotia, put up a fight before surrendering.

John Alden who raid Cape Sable Island as well as the villages around the Bay of Fundy, particularly Grand Pre and Chignecto.

[8] Shortly after Southack established himself at Shelburne, Nova Scotia, the Mi'kmaq raided the station and burned it to the ground.

[9] In response, from 17–24 September 1718, Southack led a raid on Canso and Chedabucto (present-day community of Guysborough) in what became known as the Squirrel Affair.

Southack laid siege for three days to Fort St. Louis at Chedabucto, which was defended primarily by Acadians.

On 18 September, British marines land on Lasconde's Grave and seize the entrance to Chedabucto Harbour.

The following day HMS Squirrel landed troops at Salmon River who then proceeded to the rear of the village.

HMS Squirrel made its first attempt to enter the harbour but was beaten back by the Acadian cannon fire from the fort.

After pillaging and burning the villages, on 24 September, Southack released the Acadian prisoners onto the Canso Islands without any provisions or clothing.

[13] He seized two French ships, and encouraged the Governor of Nova Scotia, Richard Philipps, to fortify Canso.

After the American Revolution, led by Thomas Brownspriggs, Guysborough was settled by Black Loyalists and soldiers of the disbanded Duke of Cumberland's Regiment and King's Carolina Rangers.

During the American Revolution, in 1780, the British officer Major General Leslie occupied John Lining's residence in Hillsborough and Hannah successfully escaped with her mother to New York.

She was given land at nearby Black Loyalist settlement Tracadie, Nova Scotia but never moved there.