The Baraboo Chicago & North Western Depot and Division Offices (Baraboo Depot) is a “combination” depot, integrating both passenger and freight functions under one roof. Railroad transportation was key to the growth and economic prosperity of European-American settlements in Wisconsin from the late 1850s into the 1920s. The arrival of the Chicago & North Western Railway in 1871 stimulated Baraboo’s development as a regional center for shipping, and brought new businesses as well as visitors touring nearby Devil’s Lake and the Wisconsin Dells. The population doubled in the decade after the railroad arrived, and doubled again by 1910. The railroad was one of the leading employers in Baraboo into the 1920s. Nearly 400 Baraboo residents worked for the railroad in 1903, the year after the present depot was erected. The Baraboo Depot is the only surviving building representing railroad transportation in Baraboo.

The Baraboo Depot has importance beyond Baraboo because it housed the offices of the Madison Division of the Chicago & North Western Railway. This was a 219-mile stretch of the line that extended from Belvidere, Illinois to Medary, Wisconsin (just east of La Crosse). From its opening in 1902 until 1933, the Baraboo Depot was the center of railroad activities in southcentral Wisconsin. Personnel in the division offices monitored and facilitated train movements along the entire line, planned timetables, designed bridges, tunnels and rail improvements, maintained financial accounts and records, and repaired engines and rolling stock for all the stations in the division. A handful of division offices were built around the state. The Baraboo Depot is one of only five known surviving division offices, lending it statewide significance.

The Baraboo Depot was designed by Frost and Granger, a Chicago-based architectural firm that designed more than 200 stations for the Chicago & North Western Railway. Charles Sumner Frost and Alfred Hoyt Granger both studied architecture at the Massachusetts Institute of Technology. Each married a daughter of Marvin Hughitt, long-time president of the Chicago & North Western Railway, which may have influenced the formation of their firm and their selection as company architects of the line.