The Caledonia Street Commercial Historic District represents the development of a prominent commercial area on the north side of the city of La Crosse. The historic district consists of a single contiguous block of masonry buildings fronting the street and a recognizable and dense historic streetscape that marks the area as a commercial satellite district, which specifically served the immediate shopping needs of people on the north side of the city in contrast to the larger commercial downtown district further south. The district has a large concentration of architecturally significant commercial buildings reflecting the continuity of architectural design trends through the mid-1960s. The district is significant for its collection of commercial buildings and represents a wide range of design influences though many of buildings possess a similar basic form.

Once part of the village of North La Crosse, annexed into the city of La Crosse, the commercial district along Caledonia Street is located along a major path north out of the city that has served as a major streetcar route and state highway. Thriving businesses along the blocks of Caledonia included dry goods stores, groceries, theaters, restaurants, taverns, pharmacies, clothing stores and various services with offices and apartment spaces above that have served the surrounding neighborhoods of north La Crosse.