
As you know, that's a big chunk of territory you have circled. Lots of small towns, and small towns are often located on rivers... and even small rivers can swell and make a huge mess out of things. Plenty of high ground around there... but driving sure won't be fun if it's possible.
I've done plenty of driving through Maryland in hurricane/tropical storm weather, and it sucks. I'm glad to trade -20 degree weather in Minnesota for hurricanes out there.