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St. Michaels, Maryland

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Did You Know … ?

  • St. Michaels was one of the models for Patamoke village in James Michener’s “Chesapeake.”
  • Chesapeake Bay is the largest estuary in North America (4,500 square miles).
  • The abolitionist, Frederick Douglass, was a slave in St. Michaels during formative teen years.
  • The Third Haven Meeting House in Easton is America’s oldest religious building in continuous use (from 1684).
  • In 2003, then Defense Secretary Donald Rumsfeld bought a St. Michaels house called Mount Misery.

Of boats and boutiques

St. Michaels is a resort town with a history. It’s a remarkably small place, with a population of less than 1,200 on the eastern shore of Maryland’s Chesapeake Bay. It was founded as a trading post in the mid-1600s.

It is called the “town that fooled the British” because, during the War of 1812, residents — aware an attack was coming — placed lanterns in trees above St. Michaels. As a result, almost all British cannonballs overshot the town.

In the 19th century and well into the 20th, the town’s economy was predominantly based on shipbuilding and the seafood processing and packing industries, but, nowadays, the top business is tourism.

It’s an inherently attractive destination, given its location on the Chesapeake and given an authentic architectural heritage that includes clapboard cottages, Victorian homes and a few estates that attract the rich and famous as residents, at least part of the year.

The town offers a charming retreat from the hassles of modern living. Guests may choose from a number of inns and bed-and-breakfast establishments — no high-rises here. The main street and a maze of side streets provide numerous options for relaxation in boutiques, markets, museums, restaurants and spa facilities.

For the more active, the area is a natural for the cyclist, but the waters of the bay are the defining come-hither attraction. Visitors can cruise the bay on a historic skipjack, charter a boat and take the helm themselves or get a lot closer to the water in a kayak. Spending quality time at the Chesapeake Bay Maritime Museum is an obvious complement to time on the water.

St. Michaels hosts a number of festivals each year, ranging from seafood events to boat festivals and boating races. Autumn is busy, too, with Halloween-themed events.

The area around St. Michaels provides appealing diversions, including driving tours to neighboring villages or, even, a journey to nearby Tilghman Island for additional outdoor activities or the ultimate retreat from workaday cares. The island has its own annual seafood festival, as well.

Things to do for Venturers

  • Buy a used boat at the Chesapeake Bay Maritime Museum. Or donate one to the nonprofit.
  • Sightsee in St. Michaels and its environs on a bicycle.
  • Head directly to the Boat Building Shed at the Chesapeake Bay Maritime Museum to see what is under construction — and take away a few pointers, as well.
  • Join a crabbing cruise from Tilghman Island. For a change of pace, also take a ghost tour of the island.
  • Spend a few hours kayaking in tidal rivers (Choptank, Nanticoke or Pocomoke) or in salt marshes of Blackwater National Wildlife Refuge or Wye Island. In the marshes, spot wading birds and possibly bald eagles.
  • Charter a sailboat and take the helm for a day on the bay.

Things to do for Centrics

  • Get married on a yacht in Chesapeake Bay.
  • Join a sightseeing tour that highlights the area’s lighthouses. The Chesapeake Bay Maritime Museum bought and moved the Hooper Strait Lighthouse, saving it from destruction.
  • Get the flavor of the area by staying in a local bed-and-breakfast inn. Also, watch a log canoe race on a summer weekend.
  • Cruise on Chesapeake Bay aboard the historic skipjack H.M. Krentz, which is berthed at the Chesapeake Bay Maritime Museum.
    Or, go fishing at the Miles River.
  • Opt in for a tastings and tour at St. Michaels Winery.
  • Eat oysters, for which the bay is famous; eat them at the autumn OysterFest if the timing is right. If they are too slimy for your tastes, eat crab from the bay.

Things to do for Authentics

  • Depart St. Michaels for a few days at luxury accommodations on nearby Tilghman Island.
  • Devote a day (or more) to browsing the quaint shops, boutiques and galleries found in St. Michaels.
    Or, shop in the county’s larger town, Easton, and work in a glimpse of the Friends’ Third Haven Meeting House.
  • Plan a romantic getaway at the Two Swan Inn (built in 1790).
  • In the season (late May through October), join a guided Saturday walking tour of St. Michaels, departing from St Michaels Museum. Or, tour in a horse-drawn carriage.
  • Have a treatment at one of the town’s spas.
  • Spend a day following in the footsteps of James Michener (who sketched out “Chesapeake” in the tavern of the Robert Morris Inn in nearby Oxford, Md.). Also, follow the footsteps of his characters.

Additional Resources

For more information, consult the Talbot County Office of Tourism at