A century of South Boston roofs runs through Gupton’s family story

When Eugene Graham Gupton began roofing work in 1920, tin, metal and wood shingles were part of the trade. More than a century later, Gupton Sheet Metal & Roofing remains in South Boston, with a company history that follows changes in both roofing materials and family leadership.

The business began in the Riverdale area. Eugene's son, Prentice V. Gupton, took a leadership role in 1951, and the company incorporated in 1956, moving to Seymour Drive. That address remains part of the firm's local identity today.

The work changed as new systems entered the market. Under Gary Gupton's leadership beginning in 1981, the business expanded into membrane roofing, including EPDM and TPO. Those systems extended its capabilities beyond the materials associated with the company's earliest years.

Tim Upchurch took over in 2015, continuing the fourth-generation business. Gupton now combines commercial roofing with sheet-metal fabrication, repairs and maintenance, serving the buildings and employers that make up the area's working landscape.

The sheet-metal component is a particularly useful thread through the history. Roofing is not only the broad surface visible from a distance; it also involves the edges, transitions and details that connect a system to the building below. Fabrication and installation are related parts of that work.

Gupton's longevity does not mean the trade has stood still. Its history is instead a record of adapting—from older roof coverings to modern membranes—while maintaining a South Boston base. For a company founded before many of today's roofing products existed, that combination of continuity and change is the central story.