The community, known as Port Royal before 1710,[2] is recognised as having one of the longest histories in North America, preceding the settlements at Plymouth, Jamestown and Quebec.

[5] By 1629, [British colonization of the Americas] renewed the settlement, this time centred around Charles Fort, which is the site of the modern town.

[14] The confluence of the Annapolis River and Allains Creek, the site of the modern town, was named Nme'juaqnek meaning "the place of bountiful fish" by the Mi'kmaq, who have lived in the area for thousands of years.

[16] In 1629, Scottish settlers, under the auspices of Sir William Alexander, established their settlement, known as Charles Fort, at the mouth of the Annapolis River.

[20] In 1733, Alexandre Le Borgne (1679-1744), the eldest surviving son of Seigneuresse Marie, petitoned to have the Seigenury restored to him, but was refused.

Under the leadership of Bernard-Anselme d'Abbadie de Saint-Castin they descended on Annapolis Royal and laid siege to Fort Anne.

Father Rale's War[a] (1722–1725) was a series of battles between the New England Colonies and the Wabanaki Confederacy, including the Mi'kmaq, who were allied with France.

During Father Rale's War, in July 1722 the Abenaki and Miꞌkmaq attempted to create a blockade of Annapolis Royal, with the intent of starving the capital.

In response to the New England attack on Father Rale at Norridgewock in March 1722, 165 Mi'kmaq and Maliseet troops gathered at Minas to lay siege to the Lt.

[23]: 6 [25][26] Under potential siege, in May 1722, Lieutenant Governor John Doucett took 22 Mi'kmaq hostage at Annapolis Royal to prevent the capital from being attacked.

[24]: 399 A key event of Father Rale's War was in early July 1724 when a group of sixty Mi'kmaq and Maliseets raided Annapolis Royal.

Jean-Louis Le Loutre, the Vicar General for Acadia, gathered 300 Mi'kmaq warriors together, and they began their assault on Annapolis Royal on 12 July 1744.

[23]: 110–111  The assault lasted for four days, when the fort was rescued on 16 July by seventy New England soldiers arriving on board the ship Prince of Orange.

[27]: 38 After spending the summer trying to recruit the assistance of Acadians, François Dupont Duvivier, officer of the French colonial troupes de la marine, attacked Annapolis Royal on 8 September 1744.

[27]: 338–341 In May 1745, Paul Marin de la Malgue led 200 troops, together with hundreds of Mi'kmaq in another siege against Annapolis Royal.

While at Cobequid, Pote reported that an Acadian had remarked that the French soldiers should have "left their [the English] carcasses behind and brought their skins.

[29]: 42–43  On July 10, Pote witnessed another act of revenge when the Mi'kmaq tortured a Mohawk ranger from Gorham's company at Meductic.

[29]: 45 Led by Ramesay, the French land forces laid siege to Annapolis Royal for twenty-three days, awaiting naval reinforcements.

[23]: 186 In December 1757, while cutting firewood near Fort Anne, John Weatherspoon was captured by Indians, presumably Mi'kmaq, and carried away to the mouth of the Miramichi River.

[32] Although invited to take part in the revolution by the Continental Congress, Nova Scotia remained largely loyal to Great Britain.

Another notable Black Loyalist was Rose Fortune who founded a freight business and policed the Annapolis Royal waterfront.

[35] The Loyalists who remained in Annapolis Royal brought an injection of professions and capital that strengthened the town as a regional centre beyond its status as a garrison outpost.

Following the replacement of sailing ships by steam in the 1880s, Annapolis Royal served as a coaling station between Saint John and Boston.

The generating station harnessed the tidal difference created by the large tides in the Annapolis Basin, a sub-basin of the Bay of Fundy.

Annapolis Royal has a humid continental climate (Köppen Dfb) and typically has mild summers, cold winters and is wet all year.

[49] Various historical walking-tours are available in the town, particularly during the summer season; one of the more well-known being the late-night, candlelight Garrison Cemetery tour.

The town acts as a significant hub for commerce within the broader Annapolis County, catering to a population exceeding 21,000 residents.

[66] In 1743, Paul Mascarene, the Lieutenant Governor of Nova Scotia, translated Molière's La Misanthrope and staged productions that winter in Annapolis Royal.

Events are held throughout the town and Fort Anne, such as live music, dances, historical reenactments and pipe bands, culminating in a parade on the final day.

[73] Annapolis Royal has two sister cities:[74] Minor planet 516560 Annapolisroyal was named in honour of the town by David D.