The River Foss was dammed in York, on the orders of William the Conqueror, to create a large fishpond, with a marsh extending to its east.

At this time, it was renamed, after Piccadilly in London, but due to its relative isolation from the rest of the city, it did not attract the hoped-for large residential properties.

[2][3] By the 2010s, the City of York Council noted that "although it contains offices, apartments and hotels, Piccadilly is not a popular destination since it has little to offer in the way of retail or visitor attractions".

[2] The Spark:York development of converted shipping containers is on the central part of the street, opposite the former Banana Warehouse.

[6] At the southern end of the street lies the Fishergate Postern Tower, part of the York City Walls.