The ford across the River Forth near the town brought prosperity and influence, as did the port that was later built. In the 12th century, King David and his successors elevated the town, then called "Strivelyn", to a "burgh". The ford, which was later expanded into a bridge, was the site of the Battle of Stirling Bridge in 1297 during the constant conflicts between the Scots and the English. In 1314, the two armies met again near the bridge at the Battle of Bannockburn.

Even centuries later the port on the River Forth brought prosperity to the city - particularly through the tea trade with India and the timber trade with the Baltic states. However, with the invention and spread of the railway, the decline of river trade began. After a railway bridge was finally built over the river, which made it possible to load goods onto ships further downstream, the port finally disappeared completely in the middle of the 20th century.

The Victorian arcade was constructed 1879 - 1882. It was the idea of businessman William Crawford, a local china merchant. The unique development comprised 2 hotels, 39 shops, a 1200-seat theatre, and 6 dwellings and cost £30,000 to construct. The Stirling Arcade is one of just five 19th century shopping arcades in Scotland.