I know that there are several of you who own older boats that are in between Baltimore and say, Herring Bay, so this may be of interest to you.
I attended my first Good Old Boat Regatta, which was hosted in Mill Creek, right near the old radio
towers by Greenbury Point. The event was well attended by around 60 boats, maybe more. The criteria is that your boat must be in a fleet where the first hull was built no later than 1975. So if your boat was built in 1979, but the first hull was built in 1975, you're ok to attend.
The event was well managed. The race committe did an excellent job of picking courses, scoring, etc. The real trick was explaining racing, and starting sequences to a bunch of cruisers and day-sailors who never race, and keeping things safe.
There were Alberg, Cal, Tartan, Pearson, PHRF divisions and a few others. A wide variety of classic boats. There was food, music and trophies. Anchorage was free and plentiful.
If I have anything negative to say about the event at all, it would be that many of the participants were clique-ish, and no one really even acknowledged my existence (except for the event staff) until Sunday afternoon.
This was only my second time racing my own boat, and I managed to correct over a Columbia 35 which was an accomplishment for me.
The event usually has almost 100 openings, and is very inexpensive and very low-intensity so I encourage any locals with older boats to consider attending next year. The Shearwater Sailing Club puts on the event, so you can check their website for information.