Sightseeing... What do you want to see? Cities? Nature? History? Beaches? Have you been out to the Washington DC area before?

You're not going to be very far from Washington DC or Baltimore... Washington DC has all the monuments and the museums. The museums are free, you can go on national park bike tours of the monuments on some weekends. Baltimore's also got a nice harbor/downtown area.

The little town near Blackwater is cute, I'm not sure I'd stay around it to specifically sight see for more than a day, I think you can wander through that town within that period... If you like kayaking, there's lots of great kayaking around blackwater... You can rent or join in some of the tours.

If you want to do nature... there's plenty of that at blackwater, but you could also head over to Assateague Island... The cutest seashore experiences are either going to be Assateague/Chincoteague... or maybe some of the Delaware beaches - rehobeth or fenwick island... Ocean city, MD is not cute.

I'm not sure how many of us are actually going this year, but in past years, people from here got together the day before to go kayaking & have dinner together, and then possibly rode together depending on ability levels the next day... But they moved the event from spring to fall this year and increased hte price, so a lot of people haven't quite registered or decided whether they will. October's a busy month with lots of other events.