I've been to Rock Hall dozens of times over the past couple years, but not because it was a great place to visit. Waterman's Restaurant was OK, but that's about as high as I would rate it. I purchased my boat from a guy who kept it at the Sailing Emporium, nice marina as far as marinas go, but nothing exceptional by a long shot. The guy that owns it is currently the mayor of Rock Hall.
Saint Michaels has a lot more to offer, more of pretty much everything, and most everything within walking distance. Pricey - yes, but so is Annapolis, Baltimore's Inner Harbor, and some other nearby places in the Chesapeake's upper reaches. One could only imagine if Aberdeen Proving Grounds were to shut down and the entire place were converted into a huge waterside resort.
WOW! Think about neat trips to Pools Island, posh restaurants, hotels, gambling casinos, maybe even another Disney-World. There are thousands of acres of waterfront property on the APG lands, most of which has been blasted to hell at one time or another while testing armament, but a lot of it is still pristine.
Havre de Grace is a neat town, some fairly good restaurants, some nice marinas, and other touristy stuff to see. Upriver, Port Deposit, which has undergone some face lifting over the past couple decades, has a few decent restaurants and a bit of history to explore.
I spent a night at Chesapeake Beach's Rod "N" Reel Dock Resort and Spa, great restaurant, nice marina, a bit shallow but constant dredging keeps the depth maintained to more than 6 feet in the center of the channel. The hotel is very nice, and there's a neat Railroad Museum there as well.
The last time I was near Tilghman Island I seriously thought about stopping in at Buddy Harrison's Chesapeake Inn and Restaurant - haven't been there in years. The last time I was there, though, the marina was getting a bit too skinny for sailboats. Might want to check that out with Captain Buddy, Jr.
Oxford was really nice, the restaurant I visited for dinner was way overpriced, but one adjacent to the Oxford Boat Yard where I had lunch served a great meal and the prices were not all that bad. The people at the boat yard were top notch and super nice to deal with. Can't say enough good things about them.
I was in Crisfield a couple years ago, and the place almost resembled a ghost town from what I remembered from two decades back. Keep in mind that Crisfield, along with many other Eastern Shore towns, was highly dependent upon the bounty of Chesapeake Bay. Not much of a bounty out there in comparison to what there was in the early 1970s, a time when that town was boomin'.
Allen Tyler's restaurant on Smith Island served up some pretty good crab cakes, steamed clams, oyster fritters, fried chicken, and other local dishes, but it was thumbs down for the clam fritter - Whoa that was nasty, at least for me. Sure did love those Hush Puppies, though.
Solomons has some pretty good restaurants, a very sheltered anchorage inside the creek, but that can get crowded on the weekends. Had a bad experience in there one night during a horrendous thunder storm.
Six miles up the Potomac River near the mouth of Smith Creek is where Scheible's Fishing Center and the Scheible's Crab Pot Restaurant is located. Captain Bruce and Ms Sally sold the complex a couple years ago, and the last I heard was the restaurant was still going strong, but I haven't had an opportunity to check it out. You can dock at the end of their pier where there's about 8 feet of water at high tide, and then it's about a 600-foot walk down the pier to the restaurant.
One of the place I hope to get to later this year is Cape Charles, Virginia, which has really changed over the past decade. When I first visited Kings Creek Marina, which was 40 years ago, you had to really watch your step walking down the pier or you had a 50/50 chance of falling through. The marina only held a couple dozen commercial fishing boats, and there was a couple rundown stilt houses there. The entire facility has been transformed into an incredible complex, complete resort and restaurant at the marina, and the town has undergone a significant facelift. You don't have to go far down the bay to get to the old Kiptopeke Ferry landing and Kiptopeke State Park. There's a fairly sheltered anchorage behind the seawall that was made by sinking a dozen concrete Liberty Ships in about 18 feet of water in front of the old landing. It's a neat place to explore.
If I didn't have to work so much, I could probably find some more locations around the bay that need exploring. Rock Hall, unfortunately, I believe will soon take the same direction as Crisfield - just another Eastern Shore waterman's town that is too difficult to access from across the bay. I just don't see it becoming another Saint Michaels or even another Havre de Grace.