Anyone interested in going to this here is some more information:
The St. Mary's River is off of the Potomac River near the mouth of the bay. One slight hop over is Smith Creek where you can find Point Lookout Marina. A few miles from there is the Point Lookout State Park, which has a nice ramp.
Anchoring in St. Mary's River is done near the college of Saint Marys. The sailing team has docks there where you can fill your water tanks us and go in for a short time. The holding there is excellent.
Anyone trailering in their boat will find plenty of places to launch that aren't too far away. You can dingy in to St. Mary College sailing dock to land and go to historic St. Mary's City.
Virginia Compac sailors could come up from the Virginia Side of the river if they launch out of the Coan River or the Yeocomico River. In the Yeocomico River there is Port Kinsale Marina that has a VERY deep ramp (it is steep). I have retrieved a boat out of there (hunter 22). http://www.portkinsale.com/Marina.htm
The northern Compac Sailors, if coming by land, could come in through several routes. Smith Point Marina would be a good place to go out of and you would remain in protected water, for the most part. In a strong North West Wind you are mostly sheltered by the MD shore of the Potomac. You would see swells out of a strong South East Wind but, most of the time, strong winds come out of the North in late September. http://smithpointmarina.com/
In my video at 1:16 you will see St. George's Point in the distance. I was sailing in a very strong North East Wind with just my 110 in the video and you see the chop is quite minimal. The St. Mary's river is off to the right. https://www.youtube.com/watch?v=QvLyijNrYFY
There is also a Coast Guard Station in the St. Mary's River.
If anyone has any questions or is interested in coming down let me know. A few years ago I went to an event similar to this one, a bit bigger, and I had a tall ship sailing into the St. Mary's River right behind me (I arrived the day before). I will probably end up in the St. Mary's River the day before the event.
Also, if you decide to do an extended stay in the area there are TONS of VERY GOOD if not Awesome anchorages near by. This is a great area.
Anyone who was at the CB get together, Colonial Beach to St. Mary's City is probably 26 miles. I routinely sail past here on the first day of a cruise when I go into the Bay. Often I sail into Smith Creek because there is an excellent anchorage there.