I can bring 1 car and I'll even bring the Guinness!
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Pssst.... if we do this in Maryland, there's a brand new Guinness Brewery that opened about 4 months ago about 15 minutes West of Baltimore City on the way to D.C.
It is the only in North America and I think the only one outside of Ireland. They offers tours and events.
Baltimore Harbor with both Camden Yards and Ravens Stadium complex, where they hold car events, and even stage the Baltimore GP, is ~15 minutes back in the other direction.
Just a thought.
Best months for this region are May - mid-July. It gets uncomfortably hot and humid after this. September is hurricane and rain season. No bueno.
Early thru mid-October can be dicey, but late October through Mid-November are generally tepid to cool but stable weather with the added bonus of trees hitting peak color in the 3rd week of October (generally).