The town and the college were mutually advantageous to each other. The townspeople financially supported the college but at the same time benefited from living in a college town. The more affluent students were an important source of income for local merchants and businesses. Moreover, unsuccessful attempts to establish a college commons, forced the majority of students to board with local families until 1880⁴.

The college students proved to be a significant part of local businesses' customer base not only in Middlebury but also in other Addison County towns and even beyond. It is not surprising then, that many store owners published ads in Middlebury College's magazine, The Undergraduate. A number of merchants offered special rates for students.

According to Stameshkin, "[it] was carefully estimated in 1905 that students and faculty spent over fourty thousand dollars a year (a significant sum for that era) in the town."

The college's expansion in the 20^th century has radically increased its importance to local businesses, many of which cater specifically to the needs of the student body as can be seen by ads in The Campus and Middkid.com