Visit St. Michaels on Maryland's Eastern Shore

Updated on June 15, 2020
Dolores Monet profile image

From popular tourist attractions to lesser-known areas, Dolores shares destinations in Maryland as well as regional day trips.

The Main Street of St. Michaels, Maryland (Talbot Street)
The Main Street of St. Michaels, Maryland (Talbot Street) | Source

St. Michaels is a small town on Maryland's Eastern Shore that just oozes charm. At just 1.5 hours from Washington, D.C., and a relatively short drive from Baltimore, Philadelphia, and Wilmington, St. Michaels has become a weekend tourist destination for the mature age group.

Located on a peninsula jutting into the Chesapeake Bay, St. Michaels is known for its quaint main street, cute shops, boating, fishing, and seafood. The flat terrain of the Eastern Shore also makes St. Michaels a great place to cycle, especially west of town where the roads are less traveled, and bordered by trees and beautiful farms.

St. Michaels is located off Route 50. Turn west onto Rt. 322 (Easton Bypass). At the fourth traffic light, bear right onto Rt 33 (St. Michael's Road) and drive about 9 miles.

A lovely old house in St. Michaels
A lovely old house in St. Michaels | Source

History of St. Michaels

St. Michaels was laid out in the 1770s by James Braddock and became a shipbuilding town due to its proximity to the Chesapeake Bay. By 1812, six shipbuilding operations were located there, drawing the interest of the British during the War of 1812.

On August 10, 1813, the townspeople got wind of a planned British attack. In order to protect the shipbuilders, main street, and homes, the people set lanterns high in the trees and on the tops of ships' masts. The British were fooled into believing the lights were the lights of the town and the cannon fire missed their intended targets.

One of the more well-known types of ships built at St. Michaels was the Baltimore Clipper, a fast-moving schooner that came in handy for outrunning blockades and pirates.

As the shipbuilding business declined, the watermen took over with crabbing and oystering. Delicious seafood is available there today with steamed crabs, soft shell crabs, crab cakes, and oysters being popular menu items in area restaurants.

In the late 1880s, steamboats filled with tourists from Baltimore began to visit towns on the Eastern Shore of the Chesapeake Bay. St. Michaels offered a few guest cottages and a lovely get-a-way from the busy urban area. It was not until the 1970s that St. Michaels popularity as a tourist destination began in earnest with the opening of the Chesapeake Maritime Museum in 1965.

The Chesapeake Maritime Museum offers indoor and outdoor displays, featuring insight into local history, local culture, fishing, and commerce in the Chesapeake Bay region. Artwork by maritime artists is often featured as well as several historic vessels.

The Hooper Strait Lighthouse, built in 1880, was slated for demolition in the mid-20th century. But the Chesapeake Maritime Museum acquired it and saved it for posterity.

Old house in St. Michaels
Old house in St. Michaels | Source

A Visit to St. Michaels

A visit to St. Michaels always includes a long stroll down its picturesque main street. Talbot Street is lined with beautiful old buildings, and cute shops offering whimsical décor, ice cream, art, and crafts.

You can find a place to go birdwatching, bring your own boat, or charter a sailboat. You can stay at an old hotel, or in one of the many Bed and Breakfast establishments.

Fun festivals and events are held throughout the year, including a folk festival, Waterman's Appreciation Day, art shows, and antique car shows.

In spring, St. Michaels hosts a wine and food festival. In fall, there is the annual Halloween Parade. And in September, the Chesapeake Maritime Museum holds its annual boat auction. Donating a used boat to the museum is tax deductible. The boats are later sold or auctioned off. In October, visit the Mid-Atlantic Small Craft Festival where hundreds of boat enthusiasts gather to show off their skiffs, canoes, kayaks, and rowboats and you can attend workshops and demonstrations relating to small crafts.

St. Michaels has been the home of several important people. Frederick Douglas lived a portion of his life enslaved at nearby Mount Misery Farm. Former Vice President Dick Cheney has a bayfront home near St. Michaels. And James Michener stayed at St. Michaels while writing his novel, Chesapeake.

In 1988, the movie Clara's Heart, starring Whoopi Goldberg and Neil Patrick Harris was filmed there. In 2004, the movie The Wedding Crashers, starring Owen Wilson, was filmed there as well.

Two of My Favorite Shops in St. Michaels

The Gregorio Gallery at 104 North Talbot Street (410-745-0927) offers an exquisite collection of fine photographs, many with a local theme. For 35 years, Pete Gregorio's first love was black and white photography. Thanks to Digital Image Rendering Technology, Pete made the switch to color as the technology allows him to recreate the scene as he saw it, although black and white 'will always be closest to (his) heart.'

The pictures displayed at Gregorio Gallery depict the area's hidden corners, back roads, and waterways with a dreamlike and mysterious quality. Rural scenes, old barns, boats, and country road present a different world, beautiful and serene. It can be hard to believe that such pastoral charm exists almost just around the corner.

Gatsby's Collection 1007 South Talbot Street (410-745-3700) Located just east of St. Michaels historic district, Gatsby's offers a unique collection of imported goods, European and American antiques, statuary (and tons of it), fountains, urns, furniture, decorating accessories, and interesting items from 22 countries. You can lose yourself in the fascinating 40,000 square foot warehouse of really cool stuff.

Old House in St. Michaels
Old House in St. Michaels | Source

Location of St. Michaels, Maryland

St. Michaels, Maryland:
St. Michaels, MD 21663, USA

get directions

St. Michaels: The Town That Fooled the British

© 2010 Dolores Monet


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    • profile image

      Patti Golden 

      5 months ago

      I’ve been to St Michaels, MD. I have two sisters who live there. It’s soo beautiful. There is a lot to do. Food is fresh & local. They have a local winery. They have two wonderful resorts with golf courses, pools right on the beach. It’s claim to fame other than the Maritime museum is the fact that there is nothing from chain companies. They have a local supermarket on Talbots Street, shops, taverns, restaurants. It is very laid back.


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