The pride and joy of the Eastern Shore is the Chesapeake Bay village of St. Michaels, a colonial-era shipbuilding center turned yachting haven that’s home to the excellent Chesapeake Bay Maritime Museum (410/745-2916, daily, $15). Located right on the waterfront at the center of town, the museum has extensive displays of skipjacks and other historic sailing vessels, which you can watch being restored in the museum workshops. There are also diverse pieces of fishing and hunting gear, plus a working lighthouse, all displayed to conjure up traditional Eastern Shore maritime life.
Although it’s full of lovingly maintained old houses and commercial buildings as well as working wharves, chandlers, and sail lofts, St. Michaels is also a major tourist trap, with all the souvenir shops you could want. The lovely harbor is lined with restaurants like the St. Michaels Crab and Steakhouse (305 Mulberry St., 410/745-3737, Thurs.-Mon.).
After seeing the museum and wandering around the town, if you want to get a feel for the unspoiled Chesapeake, follow the signs southeast from St. Michaels to the historic ferry (daily 9am-sunset, $20 per car round-trip, $5 pedestrians round-trip) that shuttles across the Tred Avon River every half hour or so between Bellevue and Oxford (pop. 651). Oxford, a truly sleepy little Eastern Shore town, has hardly changed since the 1760s, when it was one of two authorized ports-of-entry into colonial-era Maryland. Wander along the waterfront or south along Morris Street to the village center, through what may be the best-preserved colonial townscape left in America. No less an authority than James Michener, who lived in St. Michaels for many years, went so far as to say that the crab cakes served inside the circa-1710 Robert Morris Inn (410/226-5111, $145 and up), opposite the ferry dock, were among the best he’d ever tasted.