Ted William's longest home run in Fenway Park was 502 feet, but I don't know if that was his longest home run ever.
It's about 90 minutes to drive.
461 km
Its not far, probably about a 20-25 minute drive. Could take longer if traffic is bad though.
In the 1950's the players would average around 250 - 270 but a 300 yard drive was not uncommon.