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Over a five-year period, photographic and experiential data was collected about signage design, placement and context along America’s iconic legacy US highways. Over 10,000 miles were traveled and more than 15,000 photographs were taken to represent the broad range of signs, placements, and contexts representing current tastes, norms and trends, but also the nearly 100-year history of highway signage as an essential form of American visual communication. This work captures the use and evolution of road signage to communicate public safety, wayfinding, and commercial messages along historic highways routes, and establishes the special importance of the specific environmental context in which the signs are situated for determining how effectively they communicate their messages. Analyses of the signage using visual attention software tools show that identical signs with identical placement will capture visual attention differently depending on the specific characteristics of the visual context.