One of our favorite small towns, this coastal town is a bit of staid Britain on the laid-back Eastern shore.
Why We Love It: It’s a bit of staid Britain on the laid-back Eastern Shore. Founded by the English in 1778, the city of St. Michaels took that stiff-upper-lip attitude and tempered it with two centuries of rough-and-tumble shipyard workers, skipjack fishermen, and Navy sailors. Once one of the most vibrant ship building and fishing centers on the Chesapeake Bay, today the town about 50 miles southeast of Annapolis contains one of the largest collections of restored 18th-century buildings in Maryland. Elegant and earthy, St. Michaels knows how to party like a gentleman and a sailor—all at the same time.
Our Favorite Inn: The Inn at Perry Cabin
Just north of downtown on the Miles River, this 78-room English country-style inn is stylish without being stuffy. Rooms start at around $390, but crisp Frette linens on the beds, super-soft cotton robes in the baths, and some of the most scenic views in Maryland outside the windows make it worth the extra cash. Some rooms come with gas fireplaces, but on cool evenings many guests gather around the large wood-burning one just outside The Inn’s Linden Spa.
Best Place for Dinner: 208 Talbot and 208 Burger
Brendan Keegan and his brother-in-law Brian Fox create memorable meals at their eateries inside a restored 18th-century home. Diners with time for a leisurely meal make reservations for the restaurant’s prix fixe specials ($49 for four courses such as a grilled octopus appetizer and a broiled Maryland crab cakes entrée). Those wanting something quicker drop into Brendan and Brian’s burger bar for a B&B, a blackened all-beef patty covered in blue cheese.
City Center: Talbot Street
Running parallel to the Miles River for a couple of miles through the heart of St. Michaels, Talbot Street boasts a variety of art galleries and specialty stores. Near St. Mary’s Square, Guyette & Schmidt, Inc. offers one of the world’s largest collections of antique duck, shorebird, and fish decoys. Prices can soar into the hundreds of thousands, but it’s worth a trip just to see the craftsmanship. A few blocks up, Maryland artists Shella Kirchner and Kim Hannon offer locally made, beach-themed pieces at their Ophiuroidea (the scientific name for a sea star commonly known as the “Brittle Star”).
Scenic Spot: Chesapeake Bay Maritime Museum
Spread on 18 acres known as Navy Point (a bustling port filled with fishing boats and seafood packing houses), the Maritime Museum is a great place to lay down a picnic and pick up some history. The Point’s centerpiece, the 1879 Hooper Strait Lighthouse, is the most photographed structure in town, and the museum’s collection of Chesapeake Bay artifacts and indigenous watercraft is the largest in the world.