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A fire in November, 2005 destroyed the building located at 122 Main Street in historic downtown Annapolis. As we approached the task of designing a contemporary replacement for the historic site, our thoughts turned to the challenge of addressing the historic Annapolis context while balancing the programmatic advantages of an architecture that actively engages pedestrians and traffic. The front elevation of this unbuilt commission is predominantly glass allowing light to fill the second and third floor interiors. Our initial design proposes a historic masonry mask with a secondary layer of glass façade and employs a light, semi-transparent bris-soliel element to hold the face of the existing Main Street façades. This surface provides shading to the south facing interiors and its form and detailing suggests sail fabric while holding lines drawn from adjacent façades. The glass façade is pushed back to create an active transitional threshold space. Part out door vestibule, part terrace, this space intentionally blurs the division between public and private realms on all three floors.