Louisville, Kentucky is an eclectic town of architectural styles from Greek revival to Renaissance Revival to Post modernism, not to mention an entire street dedicated to artsy mom and pop stores. Louisville is second only to the New York City Soho district in terms of the number of its cast-iron facades. Many of these building's fronts have remained exactly as they were in the early 1800s. With such exquisite subject matter available, the author decided to address the age-old study of perspective and put a new twist on the assignment. Students were required to explore their community (and its architectural history) and take digital images of intriguing buildings with a two-point perspective viewpoint. In this article, the author presents a high school studio lesson that requires students to: (1) compose a photo using local architecture with two-point perspective; (2) create a composition that emphasizes form, texture, and color from this photo; (3) understand historical architectural styles; (4) practice traditional painting technique; and (5) understand Impressionist and Post-Impressionist styles. (Contains 1 online resource.)