Prescott, Ontario, has been strongly influenced by its geographic position along the Saint Lawrence River. The point at the narrowing of the river led to the persistent use of the area for military fortifications intended to give a degree of control over the river, as well as playing a significant part in regional conflicts of the 18th and early 19th centuries.

The historical navigational challenges downriver from Prescott gave it an uncommon role in Great Lakes shipping and the Saint Lawrence River trade, contributing to the development of its freight forwarding industry, which began in the early 19th century.

Prescott's history continued to be dominated by the transportation industry well into the 20th century, but it also saw the development of a significant brewing and distilling industry which began in the late 19th century.

French period

Before the arrival of Europeans to the Grenville County area, it was inhabited by the St. Lawrence Iroquois. The French began occupation of the area in the late 17th century, starting with a supply depot and fortified outpost named La Galette en route to Fort Frontenac (Kingston), which was built in the 1670s. Some sources place La Galette at Prescott, while others place it at nearby Johnstown. Fort de La Présentation was later built in 1749 on the other side of the river, at Lighthouse Point near present-day Ogdensburg, New York. This was soon abandoned in favour of Fort Lévis, which was located on Isle Royale (Chimney Island) in the centre of the river.

Battle of the Thousand Islands

The area became a battleground during the 1754−1763 French and Indian War between Britain and France, as both parties wanted to control what was a strategic stretch of the Saint Lawrence River. This led to the 1760 Battle of the Thousand Islands, when a 10,000-strong British–Iroquois force besieged the French at Fort Lévis. Despite a spirited defense by the 300-strong French garrison, the British took the fort after an extensive artillery bombardment. Afterward, the British occupied the fort, renaming it Fort William Augustus, though they soon abandoned it in favour of the older Fort de La Présentation, which they renamed Fort Oswegatchie. The ruins of Fort Lévis, and the island the fort stood on, were later submerged during the creation of the Saint Lawrence Seaway.

Arrival of the Loyalists

In and around 1775 during the Revolutionary War, America was politically divided. Many Americans were dissatisfied with British rule and sought their independence. Those who sided with the British or who remained neutral were considered to be rebels or traitors known as Loyalists, and this opposition was met with violence.Goldie A. Connell (1985) Augusta: Royal Township Number Seven. St. Lawrence Printing Co. ltd. pp. 3–16 As tensions escalated, the Loyalists were forced from their homes, fleeing north to what would become Upper Canada. The Loyalists were in a terrible position, as they had fled their homes with few to no possessions, and were unable to return to their homes as the Americans had threatened the lives of many Loyalists attempting to return or collect any belongings. The British attempted to negotiate and failed. Eventually, the British needed to do something to accommodate the misplaced soldiers and their families; in 1783, the land was surveyed along the St. Lawrence River surrounding present-day Prescott to be divided amongst the Loyalists as land grants for their loyalty the Crown.

Edward Jessup, born in Stamford, Connecticut in 1735, forfeited of property near Albany, New York by taking up arms for the King during the Revolutionary War. During the war, he founded the Jessup's Loyal Rangers who served the British. It is this group of soldiers who first settled Prescott and the surrounding townships after disbanding at the end of the war around 1783. For his loyalty and service, Jessup was awarded extensive lands from the Crown. In 1810, Jessup surveyed a townsite on top of his land, the current location of Prescott, which he named after Robert Prescott, Governor-in-Chief of Canada from 1797 to 1807. The townsite was in size. Jessup is credited as the town's founder.

The first documented appearance of steam navigation in the Great Lakes area was at Prescott in 1809, when the steamship Dalhousie was launched for service on the St. Lawrence River.

In 1810, Edward Jessup and his son laid out a townsite within Augusta Township near Johnstown, which they named Prescott in honour of General Robert Prescott, who had been governor-in-chief in The Canadas. Prescott had also participated in British campaigns in the area during the French and Indian War, being the aide-de-camp tasked with delivering the news of the fall of Fort Lévis fifty years earlier. Jessup began to take the first steps toward building a concentrated settlement by constructing a log schoolhouse along with a teacher's residence, which was built from stone.

Fort Wellington

War of 1812

Following the peace secured by the Jay Treaty, civilian settlers had begun to occupy both sides of the Saint Lawrence in large numbers. Sixteen years after its founding, Ogdensburg had a population of over 1200. There were numerous ties "of blood and trade" on both sides of the border, especially since, for merchants in northern New York, Montreal was the nearest centre of trade. Nathan Ford, the land agent for Samuel Ogden who had overseen much of the settlement of the land around Ogdensburg, was a Federalist who opposed war with Britain. Primary sources from the period discuss cross-border trade, notwithstanding the 1807 United States embargo on Britain and even the start of the War of 1812 itself. Nevertheless, the narrow stretch of the Saint Lawrence between Prescott and Ogdensburg was a strategic corridor which became a regional focal point for military activity.

Military buildup and naval engagements

In the lead-up to the outbreak of the war, eighty American militiamen were sent to Ogdensburg. War was officially declared in June 1812 and by October, there were over 800 militiamen and United States Army regulars stationed in Ogdensburg along with General Jacob Brown. Brown ordered the reconstruction of "Fort Presentation", which would ultimately never be completed.

At the declaration of war, eight American schooners were docked at the Ogdensburg harbour. Unprotected, the schooners attempted to escape potential capture by sailing to Sackets Harbor, New York, but they were quickly observed and two of them were captured by British forces, who forced the crews and passengers to disembark on an island before burning the ships' cargoes; the remaining schooners retreated to Ogdensburg. In July, the armed schooner USS Julia, along with a Durham boat carrying a US rifle company, was sent downriver from Sackets Harbor to protect the merchant schooners. However, the Julia was intercepted at Morristown by the brig HMS Earl of Moira. The merchant schooners were ultimately able to escape later in the summer of 1812. Two American colonels, Solomon van Rensselaer and Thomas B. Benedict, formed a plan around this time to raid the harbour at Prescott and burn HMS Duke of Gloucester, but this plan never materialized.

Fortification efforts

These conflicts made authorities of Prescott believe it was necessary to build a fortification in the town. In July, residents were employed to build a stockade which would be the main point of defence between Montreal and Kingston during the war. This would become the first Fort Wellington, consisting of a square blockhouse built of wood and earth with barracks, officers' quarters, stables and storerooms being added shortly after. The first fort needed to be built quickly, and as a result, it was ill-constructed and primitive. The second fort, which still stands today, was built in 1838.

In late August 1812, Prescott received news that General Brock had captured Detroit; however, in September, a surprise raid took place at Gananoque, which was poorly defended. The American raiders seized arms and ammunition, as well as set fire to a storehouse. By the fall of 1812, Prescott and Ogdensburg were maintaining friendly relations; however, in September this changed when the Americans reinforced the town and fired at convoys of bateaux moving up the river with British supplies. The British failed to retaliate at this time. A few months later, in February 1813, the Americans attacked the area again, this time at Elizabethtown (now Brockville); American troops marched to the courthouse and freed the prisoners while taking prominent citizens of the city prisoner.

These attacks by the Americans angered the British troops of Fort Wellington, who decided to take revenge on the Ogdensburg troops for their raids of the area and other provocations. The garrison, led by Lieutenant-Colonel "Red George" MacDonell, set out across the frozen St. Lawrence River on foot so that the American troops would assume they were performing a drill. Instead, the plan was for the Glengarry Light Infantry to attack the fort and barracks, while the Fort Wellington garrison attacked the flank. Initially, the 500 men stationed at the Ogdensburg fort refused to surrender; however, when British troops entered the fort the Americans evacuated the fort and retreated .

According to MacDonell's account of the following events, the troops then burned the old and new barracks, as well as two schooners, the gunboats, guardhouses, scows, and a few houses. Overall, the attack was a success for the Fort Wellington soldiers. Prescott saw no further action, and the war ended soon after in 1814.

Battle of the Windmill

Fort Wellington became part of its second conflict in 1838, known as the Battle of the Windmill. This battle occurred when a small group of American soldiers called Patriots were convinced that the Canadians across the river in Prescott wanted to be freed from British "oppression" and essentially wanted to restart the rebellion by planning an invasion. Although no war ended up occurring, a battle took place when the Patriots attempted to cross into Prescott. The currents of the St. Lawrence caused problems, trapping their vessels on sandbars before forcing them to land east of Prescott in the new town of Newport, the site of a stone windmill. This gave troops from Fort Wellington plenty of time to prepare for what they assumed was an attack. The Americans eventually surrendered to the British troops, and were sent to Kingston for trial; eleven people, including their leader, were executed as punishment.

Transport industry

Freight forwarding

Due to Prescott's location at the head of the rapids and its excellent harbour, it became a vital transfer point for freight travelling up the river. In 1810, a wharf and warehouse were built and a forwarding business was established by a William Gilkinson; it was the first of many forwarding operations in the town. Prescott exported large amounts of lumber, potash, and other goods. The forwarding trade led to shipbuilding developments also taking place in Prescott, with many ships being launched from its harbour. Prescott forwarders, by 1833, had formed well-established connections with the steamboat lines running from Prescott to Montreal which allowed the forwarders here to prosper over others in the area.

Forwarding became obsolete in the area much later, with the establishment of the railroads. The original forwarding warehouse built by Gilkinson is still standing, currently used as a museum dedicated to Prescott's forwarding industry. The building is made of stone but has been covered in white stucco. It was used as an American consulate, a lawyer's office, and later a laundromat before being purchased by the historical society in 1970.

Railway development