There are a number of small, charming, historic towns along the Eastern Shore of Maryland - not to mention many great anchorages. Obviously, we couldn’t see them all, and because of the oppressive heat, Cindy declared that we would be staying in marinas where our air-conditioning could keep us cool during the day when we weren’t out touring (as well as at night). We selected a handful to visit, based upon things we had previously read and recommendations from others. Each had something unique to offer, and it was interesting to contrast their history and how they presented themselves today.

St. Michaels was at the top of everyone’s list of “must-see” places in the Chesapeake. The first 3 times we tried to get reservations we were told they were full up and to try back later. (Annapolis was the only other place we had as much trouble trying to get a reservation!) Not only does St Michaels have high demand for their marinas, but the same is true for their B&Bs. There are a number of restaurants and shops to fill your time walking up and down Talbot Street. We really enjoyed Ava’s Pizza - try the Chefs Favorite, it was recommended to us and we are passing along the recommendation, and JoJo’s ice cream shop open until 9:30 (one of Ruby’s favorites). There was a helpful map of historic homes that allowed us to take a self-guided tour of the area near the marina. We also found the dog-walking locals to be very friendly, including a help yourself dog biscuit stash on one street corner!

The stand-out highlight of St. Michaels was the Maritime Museum. Tickets were good for two days and for good reason - there are more than enough things to do and see to fill two days. The volunteers were all very knowledgeable and enjoyable to talk with. The Museum itself is a campus that includes one of the old screw-pile lighthouses, a boat building shed where a project is always in progress, multiple examples of watercraft that are in the water and operational, and multiple “museum” buildings highlighting different aspects of the area's history associated with the Bay. The Maritime Museum alone is worth the trip to St Michaels.

Oxford has a great Safe Harbor marina with floating docks, a full-service boat yard if you need any help, and good protection from storms. This was one of the first locations where I wished that we could have put the stand-up paddleboards in the water - it was clean and inviting. There is a bit of a walk into town, but the “strand” was very picturesque. We really enjoyed our lunch at the Robert Morris Inn and Tavern (the British chef does great fish and chips!), as well as the memorabilia. The Inn and Tavern is the oldest continuously operated in the US, as is the ferry (or so they say?). The DAR chapter was having lunch in a private room while we ate. There were historic buildings and a local museum that had a timeline of the towns history that highlighted its glory days and the subsequent decline - but not much more that was open while we were there.

Cambridge, though just around the corner from Oxford, could not have been more different. While there was a church (Christ Episcopal) and accompanying cemetery from revolutionary war times, the historic period on display in Cambridge was from a much later period. Like Oxford, Cambridge was once a center of commerce with a major port and large canning operation employing large numbers of low wage workers. When the canning operation shut down the area was thrown into a recession and became a focus of civil-rights activity including notables like H Rap Brown (“burn it to the ground”) and Spiro Agnew. That said, Cambridge has found another way to bring income to their city - each year they host what has become one of the three largest international Iron Man events. And we happened to show up on this year’s weekend, when over 3000 competitors, plus friends, family, support operations etc showed up in the town. It was actually quite fun, especially when we found out that the daughter of the family whose boat was docked behind us was competing and came in first place in the Pro-Women’s Division! We also enjoyed some great restaurants - they also have an Ava’s Pizza, as well as a great bakery - Blackwater, and a great (even by Texas standards) BBQ - Lil bit of Bull. The people from the town were out in force and were very friendly sharing the history of the town, etc. Don’t miss Simon Central Market - family owned and operated for over 100 years and the Harriet Tubman Museum and mural.

Rock Hall has a nice little marina that they have gone to great lengths to make comfortable for everyone. Their claim to fame was that George Washington would come by boat from Annapolis and get a horse in Rock Hall to ride to Pennsylvania. The walk into town was a bit of a hike and Ford’s Seafood even further, but worth the walk and much less expensive than Waterman’s Restaurant next to the marina. Walking back to the boat, with our milkshakes (Get the Scoop, local ice-cream shack), we came across the town’s Mayor and City Manager siting out on the porch talking, and we had a fun but short hello how are you!

Chestertown is a bit up the Chester River, but well worth the trip. The Maryland farmlands are stunning. The marina was welcoming, with convenient pump-out, and complementary trikes. Yep - trikes. Cindy and I used them on one of their rails to trails bike path to get to the Drug Store and had a great time. Ruby enjoyed some time off-leash, running in the park. Chestertown is home to George Washington College, and classes were just starting when we were there. We learned a bit about the school talking to the students (where else but the ice cream shop), and later learned that one of Cindy’s cousins went to school there. It is a neat town and easy to walk around. While we were trekking through one day, we saw a historical marker showing the spot where George Washington visited his favorite tavern while traveling to and from Pennsylvania - the tavern was no longer there. We ate lunch at the one place open on a Monday - The Kitchen at the Imperial, which had come highly recommended, and it did not disappoint. A bonus were the historical yachts that called Chestertown their home and were used for educational programs during the summer.