Many scholars have touched the issue of international trade on the territory of Moldavian principality in XIVth-XVIth centuries. The majority of works have depictive historical character and are based on a wide range of sources. These sources include Polish Akty grodskie i zemskie, Russian chronicles, memoirs and notes of medieval travelers. The article is based on the complex approach and multiple factor analysis of economic and political processes in historical perspective. The author focuses on different aspects of multilateral trade on the territory of Moldavia in XIVth-XVIth centuries: location of trade routes; key cities and towns on these routes and their role in international trade; merchant diasporas and their trade and political interests; goods and products that played top-priority role in Moldavian international trade. Special attention is given to the roots of growth and decline of the Moldavian trade route. The conducted research leads to the conclusion that the economic prosperity of Moldavia in the period under investigation was the direct result of the project of maintaining and developing the Moldavian trade route realized by Moldavian hospodar Alexander the Good. It is owing to this project that Moldavia became an important center of international transit trade. This status had been preserved for more than two centuries and was lost with decline of the Moldavian trade route that occurred due to a variety of objective geopolitical factors.