It would take three decades after the founding of the College before the first student newspaper was published. The Undergraduate (1830-1831 and 1876-1902), one of the first college newspapers in the United States, made its appearance in 1830. Primarily a literary magazine offering student-produced essays, poetry, short non-fiction prose, that reflected the cultural values of a small liberal arts college immersed in the classical curriculum, particularly its strong religious perspective. For the first three decades of the 19^th century, news of daily events at the college were reported in the local Middlebury newspapers. Despite a growing student body large enough to produce and read a student newspaper, The Undergraduate failed to generate enough income to survive beyond its first year. The journals of student societies, such as The Philomathesian (1833-1834), shared a similar fate.

A second attempt at a student-run newspaper, a reincarnation of The Undergraduate, appeared as a monthly in 1876. A reflection of the growing secularism of the student body in the post-Civil War years, the new journal offered a broader academic, religious, and social perspective and an increasingly independent world view.  Student literary efforts were still included, but the focus of the new Undergraduate focused on news of the College as well as commentary on local and national issues and events of interest to students, faculty, alumni, and townspeople. News of student activities in other colleges and universities, especially in New England, was a regular feature. This time, The Undergraduate survived for twenty-five years until 1902, when the journal folded once again owing to lack of funds.