Is it possible and feasible to take a day trip by train from Milano to Pesaro in early October?
Look at Trenitalia (using Milano Centrale for Milan) or Loco2 for train times on your date. It is a 2.5 hour trip each way, or 3.5 if you insist on a direct train, so looks feasible at a stretch if you need to go to Pesaro - a place I don't know anything about, in full transparency.
For a day trip, you double the train time and then add a couple more hours for the 4 trips going to and from stations. The fastest train takes 3:22, so that amounts to over 8.5 hours in transit.
Day trips I avoid any taking more than 1.5 hours.
they have a nicely preserved Castle built in the 15th Century, the usual cathedral from the middle ages on the good old usual square with porticoes and the trivial aqueduct ... I suspect either family roots or a Rossini fan here. Pesaro is a classic day-trip from Urbino or from the seaside resorts, not from Milan.
Thanks for the input. Family roots is the answer.
I did not get into Pesaro proper, but it is in a lovely area--do take a few days to get there when you can!