、。
Hmm, judging by the face, from Shanghai perhaps.
Literal
Hmm, countenance [from-から] judging-by Shanghai [from-から] [question-か].
A detective-like musing. 相貌 (countenance/physiognomy) is a literary word for facial features. ~から判断するに is a formal construction: 'judging by.' The sentence is fragmentary — no verb for the conclusion, just 上海からか trailing off as speculation. う~む is an exaggerated, deliberative hmm.