Webb -
I don't know what you like to do before gigs, but if you or the guys you'll be travelling with are into historic stuff, there are a couple of things in Annapolis that I've always found interesting. Both of them are on the grounds of the Naval Academy ("the Yard" to Annapolis locals). You have to walk onto the campus (no private vehicles allowed except USNA employees), and even as well-known of a person as the Last of the Full-Grown Men will have to show ID.
One is the crypt of John Paul Jones, located in the lower level of the USNA Chapel, and the other is the USNA Museum, which houses one of the best collections of model ships.
Garrett Park Guitars is a very nice guitar shop, one of the first (maybe THE very first) dealer of Paul Reed Smith guitars. It's not within walking distance of the Ram's Head, but not very far of a drive.
The PRS factory is just across the Chesapeake Bay in Stevensville, and if you come through Delaware and Maryland's Eastern Shore on the way from Philadelphia to Annapolis, it's right on the way.
A point of minor interest would be the Annapolis Courthouse, located on Church Circle, about a block and a half from the Ram's Head. This is where Mrs. Glom and I tied the knot, two days before WebbFest IV, which we attended as part of our honeymoon.