By the 15th century, a fortified settlement was located near the Kremlin, where poorer layers of the population and craftsmen lived. The Kremlin and the settlement were connected by the only drawbridge, Glebovsky Bridge, which was raised to the walls during sieges. The modern stone Glebovsky Bridge was built in the 19th century simultaneously with the Cathedral Bell Tower and now connects Cathedral Park with the Kremlin.

From the 13th to the 18th century, when the Kremlin reached its maximum development, there were four gates on its territory, built into towers and leading in different directions from the city:

Glebovsky Gate and tower led to the settlement and the Great Moscow Road;

Secret Gate and tower led to the city pier;

Ipatsky Gate and tower led to the Vladimir Road;

Ryazan Gate and tower led to the Great Ryazan Road.

In addition to Glebovsky Bridge, there were two more bridges under the Kremlin walls, crossing the Lybed River near the Ipatsky and Ryazan Gates. All bridges were wide, made of seasoned oak, and had railings.