Its name derives from the rake-shaped gate that in medieval times, at night, separated the citadel built around the castle from the surrounding countryside.

The oldest part of the street is the upper one, where the houses seem to continue one inside the other, while the lower part developed during the 17th century, with buildings shaped like closed blocks around internal courtyards overlooked by overlapping balconies. For centuries, Via Rastello was the city's main commercial thoroughfare, home to numerous merchants' and artisans' shops.

It seems that even in the 19th century, during morning rush hour, traffic here was frenetic, due to the constant coming and going of people and carriages, which was joined, in the latter part of the century, by the tram. Shoppers flocked from the Isonzo and Vipava Valleys, territories then included in the province of Gorizia and later passed to Yugoslavia in 1947. Remnants of that bygone era remain in the many shops, taverns, and artisan workshops, which still retain their original windows, signs, and even furnishings.