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 Church of the Holy Rude is the medieval parish church. It is named after the Holy Rood, a relic of the True Cross on which Jesus was crucified. The church was founded in 1129, but nothing of this early structure now remains due to a fire in 1405.

Rebuilding was completed in 1414. The fall of the House of Douglas caused devastation in Stirling, possibly also damaging the church. King James II ordered a new church to be built on the same site in 1456. Construction was initially completed in the 1470s.

The second construction phase began in 1507 with plans to build a transept, a choir and a crossing tower, which would result in a cruciform basilica. The work progressed slowly. With the Reformation, they were finally abandoned unfinished in 1546. After a dispute in the course of the 17th century, the parish split and the Church of the Holy Rude became home to two congregations. Around 1818, the building was extensively remodelled and partly extended, which greatly diminished its original character.