A popular Eastern Shore destination, St. Michaels nestles along the Miles River on a peninsula that affords multiple water views. Located between Tilghman Island, Easton, and Oxford, it’s a leisurely drive from Baltimore or Washington—or an even more leisurely sail up the Miles River.
Whether you’re sailing into the harbor, attending one of the town’s many festivals and special events or simply looking for a relaxing getaway, St. Michaels offers something for everyone. The streets of this compact, highly walkable town are lined with distinctive cottages, shops, and restaurants, and there are plenty of maritime and historic sites that harken back to its early days.
A PIECE OF HISTORY
Once called Shipping Creek, St. Michaels dates back to 1632. It was a noted shipbuilding center by the time of the American Revolution, and during the War of 1812, earned the affectionate moniker “the town that fooled the British” when residents learned that British barges planned an attack and hoisted lanterns to the masts of ships and treetops to trick their enemy into overshooting the town. Only one house was struck by cannon fire; known as the Cannon Ball House, it’s still a private residence. The shipbuilding industry ended here more than 150 years ago, but today St. Michaels is one of the best-known yachting centers on the East Coast and draws thousands of sailing enthusiasts annually.
Among the historic sites in St. Michaels, the Chesapeake Bay Maritime Museum boasts an 18-acre waterfront campus, which includes Navy Point and the historic Hooper Strait Lighthouse, offering the best view in town. The museum houses the nation’s most complete collection of Chesapeake Bay artifacts, visual arts, and indigenous watercraft. Exhibitions, public programs, and a working boatyard illustrate the bay’s maritime history and culture, focusing on unique regional watercraft and boat-building traditions; boating and navigation; waterfowl; seafood harvesting; and recreation.
Also worth a visit is the St. Michaels Museum, located on the former site of the high school. This three-building complex includes the home of 19th-century white waterman Jeremiah Sewell; the Chaney House (ca. 1850), owned by free African-American brothers; and the Teetotum Building (ca. the 1860s), once a commercial structure. The buildings were moved here from other St. Michaels locations and house historical artifacts that reflect the history of life, commerce, and culture in the region.
A docent-led or self-guided walking tour of historic St. Michaels will take visitors past the Cannon Ball House; the Amelia Welby House (ca. 1775); and St. Mary’s Square, home of the Mechanics Bell (installed in 1841 to measure the workday for the ships’ carpenters) as well as the remains of a cannon used during the War of 1812.
EVENTS AND ACTIVITIES
Life revolves around the water in St. Michaels. If you don’t have a boat of your own, sailing, motor and fishing charters are widely available from May to October. Festivals also abound beginning in the spring. Enjoy the Eastern Shore Sea Glass and Coastal Arts Festival in April; WineFest at St. Michaels, also in April; and St. Michaels Running Festival in May. And coming up shortly: Fall Into St. Michaels celebrates the Eastern Shore’s fall foliage on October 24 and 25 with autumnal activities like pumpkin-carving and pie-baking contests. In addition, Oysterfest—featuring live music, boat rides, documentary films and an oyster-stew cooking contest—takes place October 31. From December 11 to 13, Christmas in St. Michaels transforms the town into a Currier & Ives Christmas card with ticketed and free events including the Tour of Homes, Holiday Gala, Breakfast with Santa and the largest holiday parade on the Eastern Shore. Visitors can get an early start on their shopping with Midnight Madness on the first Saturday in December, when shops stay open until midnight, with sales, refreshments and prize drawings.
Not surprisingly, seafood is on virtually every menu in town. The Crab Claw Restaurant, open from March through November, specializes in seafood and—you guessed it—crabs, with a spectacular harbor view. A “distinguished restaurant of North America,” 208 Talbot boasts a casual atmosphere with innovative cuisine, while Bistro St. Michaels recreates a classic Parisian bistro. Stars, at the Inn at Perry Cabin by Belmond, offers an eclectic menu with a stunning view of the Miles River and a delightful afternoon tea.
Chain stores haven’t hit St. Michaels yet, so it’s a perfect spot to look for unique gifts. A Wish Called Wanda sells American handcrafted designs in jewelry, art glass, pottery and home and garden décor; Ophiuroidea features coastal-inspired art, home furnishings and gifts by local artisans; Come by Chance offers gifts and items for the home, and the Chesapeake Bay Maritime Museum Store has everything bay- and boat-related.
St. Michaels makes an ideal day trip, but if possible, spend a few days and get to know this corner of the Eastern Shore. There are a number of lodging options, from vacation-home rentals through Eastern Shore Vacation Rentals (easternshorevacations.com) to resorts such as the Inn at Perry Cabin by Belmond (belmond.com), Harbourtowne Golf Resort & Conference Center (harbourtowne.com), St. Michaels Harbour Inn, Marina & Spa (harbourinn.com) and Five Gables Inn & Spa (fivegables.com). For more information, visit stmichaelsmd.org.
Writer Carol Sorgen is based in Baltimore.