The earliest record of Orla available in the archives is from 1507: the King bestowed on Jaśko Iwanowicz, Clerk and Trocki Voivode, the areas where today’s Orla is located as well as adjacent areas in Bielski district. Together with the bestowal, the King granted Iwanowicz the permission to found a town, which took place later. The mention of Orla from 1529 concerns the Bohawitynowicz family, who lived in this locality. In 1585, Orla became the property of the Radziwiłł family as a dowry. In 1618, Krzysztof Piorun Radziwiłł granted Orla the privilege allowing both Christians and Jews to settle down freely in the town. He also built a town hall and established a town council, composed of a village-mayor, a clerk and six aldermen. In 1622, Krzysztof Radziwiłł built a castle and a Calvinistic church. In addition, he erected an impressive manorial complex with a palace, Italian garden, sacred objects and a huge farm. The Saint John the Evangelist Chapel, the castle church, was an integral part of the complex. Sadly, no remains of the castle have survived until today.

The town suffered heavy damage during Swedish invasions; it was when the population numbered dwindled sharply. All local Calvinists perished during military clashes. This may be the source of a tale (the authenticity of which lacks any validation and hence is doubted by historians) that the Orla synagogue is the old Calvinist church. As it goes, the building was bought by Jews from Radziwiłł’s wife for a fairly big amount of money. One of conditions for the deal to be clinched was deriving the whole amount in petty 1 grosz coins. The requirement was met. Today’s sources, however, refute this theory and treat is as a legend and nothing else.

Since the 18th century, Orla began to gradually lose its importance. The reasons for that included the issues of town ownership and territorial changes in Poland.

In 1938, a large fire ravaged the greater part of the town. As local stories suggest, it was caused by a negligent Jewish woman. During World War II, there were two ghettoes in the town; later Jews were transferred to the ghetto in Bielsko Podlaskie, and later to the extermination camp in Treblinka.