Constructed in 1892, the Rupp Building, also known as the Rupp-Schmidt Building, is a testament to Victorian Romanesque architecture. What sets this building apart is its incorporation of golden brick in the façade, a distinctive feature not commonly found in other Romanesque structures in the area. The building is crowned with a mansard roof, adding to its unique aesthetic appeal. 

One striking feature of the Rupp Building is the bear's head positioned above a shield on the northeast corner. This shield not only adds to the building's character but also bears the construction date, marking the historical significance of the structure.

The location of the Rupp Building is as significant as the structure itself. The southwest quadrant of Continental Square, historically known as Tyler's Corner, has been a hub of activity and historical events. It was near this area that James Smith, a signer of the Declaration of Independence, had his office. This office played a crucial role during the Continental Congress's stay in York, housing the Committee on Foreign Affairs. Additionally, a tailor shop in this quadrant was the workplace of a young Isaac Singer, who would go on to invent the Singer sewing machine.

The Rupp Building, with its unique architectural features and historical location, is more than just a structure. It's a piece of York's history, symbolizing the city's evolution and its rich architectural heritage. In preserving these structures, York not only maintains its physical history but also honors the legacy of those who have walked its streets.