A historic waterfront town on the eastern shore of Maryland, St. Michaels is one of the favorite stops for people cruising on the Chesapeake. With several marinas and a lot of waterfront activities, it can seem like boating central during the season; on the other hand, it’s small enough (only one square mile with about 1,200 people) so you can get away from it all, if that’s what you have in mind.
St. Michaels’ appeal is not a secret. Indeed, USA Today once named it one of the Top 10 Best Small Coastal Towns, and Coastal Living said it was one of the Ten Most Romantic Escapes in the U.S.
I have to admit that St. Michaels has been one of my favorite destinations since Dan Fales, my late colleague at Motor Boating & Sailing, took us there for an overnight while we were delivering a Bertram 46 from Norfolk up to Norwalk, Connecticut, probably 35 years ago. We had dinner at the Crab Claw, St. Michaels’ iconic waterfront restaurant, and I’ve been back many, many times ever since.
St. Michaels has a rich history, dating to the 1770s. It quickly became a ship-building center that attracted British attention in the War of 1812. On the night of Aug. 10, 1813, a British landing party destroyed the town’s battery, and British ships bombarded the shore, but they failed to destroy the shipyards. The town turned to the oyster industry throughout the 1800s, and in the past few decades it has developed into a picturesque boating community and summer weekend destination.
St. Michaels is certainly easy to get to. It’s only 25 nm across the bay from Annapolis with a protected harbor on the Miles River. The first thing you’ll see coming in from the bay is the landmark Hooper Strait Lighthouse on the grounds of the St. Michaels Chesapeake Bay Maritime Museum at the entrance to the harbor.
Set on 18 acres on the grounds of what was once a crab and oyster packing factory, the museum now has more than 100 boats and boat models, art work, guns and all kinds of Chesapeake artifacts, plus lots of interactive exhibits. You can help build a wooden skiff on the Apprentice for a Day program, for example, or practice harvesting seafood by hauling in an eel or crab pot. The museum’s boat collection includes the last sailing log-bottom bugeye, and a dredgeboat built in 1909.
For marinas, the Higgins Yacht Yard is a full-service spot with 30 slips in a great location. Once past the lighthouse, leave the Crab Claw to starboard and the marina will be dead ahead. It’s a first-rate marina; I’ve stayed there many times. It’s a short walk to town, and you also can stay at the Log Canoe Inn next to the marina with six waterfront suites overlooking the harbor.
St. Michaels Marina is much larger, with 55 transient slips, and it’s also a short walk to town. The marina can hold boats up to 220 feet, and it will deliver diesel fuel to your slip. A marine store there has charts and the usual nautical accessories.
Once on shore, you can wander down Talbot Street for shopping at boutiques, coffee houses and antiques stores. If you want exercise, there are lots of bike trails in the area. There are also lots of B&Bs and small inns. For an upscale experience, The Inn at Perry Cabin will send a Hinckley Talaria 55 to pick you up in Annapolis, if you’ve left your own boat at home. Read more: