Buy the book "6 Shanghai Walks" or its successor "6 more Shanghai Walks". I have the original and Walk 4 (French Concession) is my favorite, though I've done a mix of Walks 1-3 too.

Buy the book, read the walk before getting into SH, and then follow it step by step (with small camera in hand). Also be sure to stop by any coffee shops, stores, galleries, etc that are en route and interact with people. You will be surprised by how many people (usually younger) in the shops and galleries can speak some English and will engage you in some friendly chat even after its clear that you won't buy anything.

Shanghai (not Pudong) is very very walkable.