Long before it was known as Windsor, the area around the junction of the Avon and St. Croix rivers was known by the Mi’kmaq as Pisiguit, appropriately meaning “Junction of Waters”. The rivers empty into the nearby Minas Basin, which allowed ships to sail from the Atlantic Ocean, up the Bay of Fundy and down into the heart of the province. The fertile headlands around these rivers made for ideal farming and Acadian settlers to the area did just that, erecting mills along the rivers to harness their power.
With the French and English battling over North America, the Acadian settlers became caught in the middle of the conflict. Shortly after settling Halifax in 1749, the British moved into the Pisiguit area and built Fort Edward to watch over the Acadians and discourage further development. Fearing for the safety and resenting the fort’s ominous presence, most Acadians left the area for other parts of the province. It was in 1764 that the township of Windsor was settled by New England Planters, who laid claim to the former Acadian farms and built their own homes and businesses. A year later, the town held its first agricultural fair to celebrate the area’s bountiful harvest – an annual tradition that continues to this day, making it the oldest and longest-running agricultural fair in North America.
The town of Windsor also became an important stop for anyone travelling between Halifax and the Annapolis Valley. Crossing the Avon River with horses and wagons was only possible by fording the mud flats just above the town during low tide, while people could hire a ferry during high tide. By 1837, Windsor was the site of a wooden toll bridge; however, the structure wasn’t able to bear the weight of trains and passengers still needed to disembark, cross the bridge by stagecoach to transfer to another train on the other side.