I'd love to do Chincoteague Island -- that's almost 2.5 hrs one-way for me and would entail me not having to cross the Bay Bridge to the Dark Side which I try to avoid. But it's a haul for y'all, probably more than a day ride. But hell, if you want to go to Chincoteague for whatever reason, now's the time before the summer heat and crowds.
But if that won't work, I guess I could do Cobb Island or Indian Head but the 301 route brings me through the frontier territory of the DC Wasteland -- not much fun at all. If it were up to me, we'd stay away from the Potomac and head East to the Patuxent or maybe as far as the bay. natalena, you're from that area, do you know anything that is straight due east of Dahlgren VA? Dahlgren is only 2 hrs from Yorktown. Solomon Island would be a good destination geographically but I've never been there and it's possible all the places there cater to the yachting set -- not exactly the desired ambience for moto people. There's Trader's Steak House in Chesapeake Beach that has a big deck and is frequented by two-wheelers of the 'biker' persuasion. I was there once and had the feeling everyone was afraid they were going to get beemer juice on them.
Anything on the Eastern Shore is going to be a haul across the CBBT for stokester and the Bay Bridge for natalena and myltle. I love riding over here because you can ride for miles without seeing a car. . On the other hand, it's flat as a pancake so if you're into hills and twisties, best to stay west of the bay.
Johnny gets anywhere a half hour from wherever his so he doesn't care where we go.