WC, I've never fished Virginia, but I believe the Spottail(Red Drum) will be runnin' pretty hard in Oct. Try some cut mullet or some blue crab for these monsters.
I know down here in Oct the bonnitheads (type of hammerhead shark) are coming into the shallows and rivers to give birth. They are so plentiful that they almost become a pain in the butt. You are only allowed to keep 1, but you'll catch enough to fill a truck! Use squid for the shark and everything else.