The area to the east of the University Green bordered by Colchester Avenue on the north, the Fletcher Allen Hospital Complex, Medical College, and Stafford Hall on the east; and Main Street to the southeast, is topographically more complex than the University Green. The area is a sloping tiered plateau falling behind the University Green bounded on the east by a ridge whose highest point is designated by the water tower. The southeast part of the campus originally housed the University Farm. Converse Hall (1895) - the first to be erected on the ridge of the eastern perimeter of the Main Campus- served as the first women's dormitory. Three additional dormitories--Chittenden, Buckham, and Wills-- were constructed in 1947 below Converse to accommodate the influx of students after World War Two. These three dormitories are aligned on a north-south axis further defining the Main Campus in the shape of a quadrangle whose northern boundary is the Robert Hull Fleming Museum (1931). In the 1950's and 1960's, Main Campus became subdivided into two quadrangles whose center became the new Bailey Library (1960).

With the increasing interest in the arts on campus in the mid-1960's, a proposal to create a Fine Arts Complex on the northern half of the quadrangle was developed by the Chicago architectural firm of Weese and Abramowitz. The proposed Complex featuring the Fleming Museum as its core, was to have included new facilities for Art, Theater, and Music, all to be visually contained by a grove of black locust trees, the landscape design of Dan Kiley and Associates. A reflecting pool and an identical version of the Bailey Library was to have been eventually built at the southern end of the Fine Arts Quadrangle To the north, the Fleming Museum would reverse its principal entrance from Colchester Avenue to the rear of the building.

The Locust trees and the altered entrance to the Museum are in fact in place although, the Complex was never built, as the Vermont State Legislature appropriated monies instead for the renovation and additions to the State Colleges (Lyndon, Johnson and Castleton). Instead, part of the space allocated for the Complex was dedicated to The Kalkin School of Business (1987), and the area designated for the reflecting pool and library addition remained a campus green. As a result, today, the Department of Art (studio art, art history and art education) is housed in Williams Hall, and the Theater Department, formerly located in the basement of the Fleming Museum, now occupies the University's first gymnasium (Royall Tyler Theater). The Music Department is now part of the Southwick Complex on Redstone Campus.

The southern part of the Main Campus --The Library Quadrangle-- is a geometrically complex configuration with a building perimeter and pedestrian pathway making it one of the most highly traveled and identifiable spaces on campus. The Quadrangle's eastern boundary is defined by the Marsh Life Science Building (1965) and the Aiken School of Natural Resources (1982), both of which are sited on the eastern slope of the Quad leading to the water tower. Bailey-Howe Library as a complex defines the northern perimeter, the Howe addition of 1980 creating a connecting elbow, inflecting the space to the west and the south.

There is a plateau and bowl-like area in front of the Library's portico, which with its stepped seating provides one of the most populous gathering places for students. When the weather is temperate, this area is referred to as the Bailey Beach! Throughout the year it is also the site of many student events including the annual rite of spring Maple Sugar on Snow Festival. The walkway from the Library to the University Store passes a University Bulletin Board, further defining the boundary of the Library Quadrangle to the west. The Carrigan Dairy Science Building (1949), former home to the popular university dairy bar for decades, defines the boundary to the southwest. The Terrill Home Economics Building (1951) and the library parking lot complete the southern boundary of the Library Quad. In the south east corner of the parking lot is a pedestrian walkway which leads to the tunnel taking students under Main Street to Redstone Campus, the Living Learning Complex and Dormitories, and the Athletic Complex.