In illustrative embodiments, a modular telescoping ladder system may include structural parts that can be assembled into a variety of structures. The components of the telescoping ladder system may include at least two telescoping ladders that can be connected in several ways by incorporating as joining features into the ladder assemblies. To accomplish a coupling of two ladders, joining features can be added to each ladder that enable their connection. These features may be holes through which pins may be inserted to connect two or more ladders. These joining features may be added to an accessory component that allows the joining capability to be added to or removed from a given ladder, such that the ladder can include or not include these additional features. The telescoping ladder system may be assembled into a wide variety of assemblies based upon modules selected, including, double length ladders, A-frame ladders, or scaffolds.