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Subseries 2.1: City Planning, 1960-2012, contains materials that Sullivan created in his role as City Planner, or that relate to city planning functions. Types of materials include photos and other documents related to the Northeast Urban Redevelopment Project, newspaper articles about city planning and the growth and development of Harrisonburg, and documents relating to zoning and historic district status. The folders titled "What do you think of Federal Aid? Photos and description," contain a document written in 2012 by Sullivan explaining the history of urban redevelopment in Harrisonburg, and his role in the "slum clearance" projects of the 1950s and 1960s.

Subseries 2.2: Harrisonburg History, 1958-2008, contains materials collected by Sullivan that relate to the history of Harrisonburg, as well as materials he created related to the history and development of the city. Sullivan was known as the "unofficial historian of Harrisonburg" and materials in this subseries document the history and development of Harrisonburg. Items of note include original drawings of downtown Harrisonburg from the 1950s and 1960s as well as posters and brochures that contain Sullivan's sketches for the 1980 Bicentennial celebration. Other materials include the text of various talks Sullivan gave on the history of Harrisonburg to various groups in town.