The earliest chronicle record in «The Tale of Bygone Years» about Orsha — about the capture «at Rshi near Smolinsk» of the Polotsk prince Vseslav Bryachislavovich and his two sons.

Orsha became part of the Vitebsk Principality and was attached to the Grand Duchy of Lithuania, becoming a border town.

By order of Prince Vytautas, the construction of Orsha Castle was started. It lasted about two hundred years.

On July 15, the Orsha banner, as part of the Grand Duchy of Lithuania's army, participated in the Battle of Grunwald.

Orsha — a state-owned estate, the district centre. The five‑tower stone two‑storey castle was almost completed.

On December 13, the city was granted Magdeburg rights and its coat of arms: on a blue field of a Baroque shield a silver cross, below which a golden crescent with its horns pointing upward.

After the first partition of the Polish–Lithuanian Commonwealth, Orsha became part of the Russian Empire and became the centre of the Orsha province of the Mogilev Governorate.

On 6 (18) July the city was captured by French troops. Henri Bail was appointed the intendant of Orsha (later known as the writer Stendhal).

The railway Smolensk — Brest has been built. Orsha becomes an important transport hub.

The Great Patriotic War. In the battles near Orsha, the BM-13 rocket launchers — the legendary "Katyushas" — were used for the first time. On June 27, 1944, the city was liberated.

Orsha was awarded the Order of the Patriotic War 1st class for the bravery and resilience shown by its residents during the years of the Great Patriotic War.

Since April 1, the city of Orsha and Orshansky district form a single administrative unit.