Abstract: The article studies the history of the development and functioning of the main road from Pskov through Gdov to Ivangorod and Narva, which was actively used in the pre-Petrine era. This route can be considered as one of the typical examples of the Pskov borderland road. Written and pictorial sources of the XVII century allow us to reconstruct individual sections of the road, assess the quality of the road surface and infrastructure, and characterize the peculiarities of travelers' everyday life. The main sources were the texts of the 1616 report of the Dutch envoy Albert Joachimi, the painting of road routes from Pskov in 1656, the "Notes on Russia" of 1674 by Eric Palmquist, the entries of the "Diary" of General von Allart for 1700. Trips from Pskov to Narva were made along the traditional (long) route and two short roads. Travelers encountered many troubles characteristic of the border roads – poor condition of the road surface, lack of inns, lack of road signs, bad weather, threat to health and property. The maximum average speed of a trip along the studied road is 61 versts per day. The typical average speed of a summer trip is 30 versts per day. Most of the goods between the cities were transported by sleigh from December to March, the road network of the Pskov border region was more adapted for winter trips.