Overview
St. Michaels is in Maryland, a state in the United States of America. St. Michaels is a collage of churches, manicured colonial, federal and Victorian homes, historic heritage, diverse artistic talents, and pleasant Southern culture. It is also the proud cradle and repository of the Chesapeake's maritime history.
It's a town in constant contrast, from horse-and-buggy, steamboats, watermen's deadrises, century-old log canoes and ancient buggies to ATM's, the Internet, luxury Town Cars and fancy cabin cruisers.
It's a shopping mecca with a wide array of fashionable clothing, antique and artisan shops aimed at ardent collectors. It's a galaxy of specialty food shops (including candy and ice cream) and superb nationally-renowned restaurants destined to delight even the most demanding gourmet. Of course, succulent Chesapeake seafood, fresh from the harbors, is the regional specialty.
2 sights · 1 things to do · 2 places to eat · 3 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about St. Michaels
Chesapeake Bay Maritime Museum
Brings to life the story of Chesapeake and its people with nine exhibit buildings and the world's largest collection of traditional Bay boats. Explore our 1879 Hooper Strait Lighthouse, working boatyard, and hands-on dis…
St. Mary's Square Museum
The museum offers a walking tour brochure (which you can also print out from their website), which is a great way to really get to know the town. Docent led tours are also available for $10/$5 during open hours, by appoi…
Skipjack H.M. Krentz
Public two hour boat tours cruises April-October departing from the Crab Claw Restaurant.
Plan your trip
Best time to visit & weather
Most comfortable: Apr–Jun, Sep–Oct. Summer highs reach about 90°F; winter lows dip to about 30°F. Very hot (Jul) — plan outdoor time for mornings. Wettest: Jul and Sep. (climate data from nearby Baltimore)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- BWI Baltimore/Washington International Thurgood Marshall Airport, Baltimore — 36 mi away (major hub). Directions
- DCA Ronald Reagan Washington National Airport, Washington — 44 mi away (major hub). Directions
US-50 is the main route to St. Michaels, which lies about 30 miles south of the Bay Bridge. Heading south from the bridge, take a right on MD-322, then another right on MD-33/St. Michaels Rd. From D.C., the ride is about two hours; from Annapolis, one hour; from Baltimore, one and a half hours.
Full “Get in” guide ↓Budget & where to stay
No prices are listed for this place yet. See the Sleep guide ↓ for options.
Sample 1-day itinerary
Day 1
- Morning Chesapeake Bay Maritime Museum, St. Mary's Square Museum
- Lunch The Crab Claw Restaurant
- Afternoon Skipjack H.M. Krentz
- Dinner Shore Restaurant and Lounge
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Map
Every listing with a location. Tap a pin for its Google Maps link.
Understand
St. Michaels is on the Eastern Shore of Maryland and is a historic waterfront town that has kept its small town character with lots of charm and Chesapeake Bay romanticism. It is a popular B&B spot or many come by boat for the good seafood and slow relaxed beauty of the place.
St. Michaels is an area rich in history. In the dark morning hours of August 10, 1813, a number of British barges had planned an attack on the town and a fort on the harbor side. The residents of tiny St. Michaels, forewarned, hoisted lanterns to the masts of ships and in the tops of the trees, tricking the British by causing the cannons to overshoot the town. This first "blackout" was effective and only one house was struck. Now known as "The Cannonball House" a cannon ball penetrated the roof and rolled down the staircase as Mrs. Merchant carried her infant daughter downstairs. The house still exists as a private residence.
St. Michaels derived its name from the Episcopal Parish established there in 1677. The church attracted settlers who engaged in tobacco growing and ship building.
In 1805, an area was set aside for a public market known as "St. Mary's Square". Here stands a bell cast in 1841 which rang at 7AM, noon, and 5PM to measure the workday for the ship's carpenters in the nearby harbor and the remains of a cannon used in the defense of the town during the War of 1812.
Movies
Moviegoers may recognize the look of St. Michaels, for the two blockbusters filmed here: The Wedding Crashers (2004) and Clara's Heart (1988).
Get in
By car
US-50 is the main route to St. Michaels, which lies about 30 miles south of the Bay Bridge. Heading south from the bridge, take a right on MD-322, then another right on MD-33/St. Michaels Rd. From D.C., the ride is about two hours; from Annapolis, one hour; from Baltimore, one and a half hours.
By boat
St. Michael's Marina +1-800-678-8980, offers dockage by reservation.
Get around
Because St. Michaels is so small, it is very easy to navigate by foot. There is even a 1.3-mile-long paved trail for walking and biking if you prefer to see a little bit of nature.
See
See Chesapeake Bay Maritime Museum
Brings to life the story of Chesapeake and its people with nine exhibit buildings and the world's largest collection of traditional Bay boats. Explore our 1879 Hooper Strait Lighthouse, working boatyard, and hands-on displays. Discover exhibitions detailing the Bay's roll throughout history, oystering, steamboats, waterfowling, and more.
Do
Concerts in the Park run throughout the summer, Thursday nights.
Eat
Eat The Crab Claw Restaurant
Has an extensively large amount of seafood on their menu, and they are known locally for their steamed crabs. The business evolved from a clam-shucking business established in the 1950s.
Eat Shore Restaurant and Lounge
Reservations. Indoor and outdoor seasonal dining throughout the day. This contemporary, casual restaurant focuses heavily on local and exotic seafood, incorporating only the freshest local vegetables and herbs.
Sleep
Stay Harbourtowne Golf Resort and Conferences Center (Harbourtowne County Club)
A 153 acre waterfront resort in a natural setting offering 111 guest rooms, meeting and conference facility, Pete Dye designed golf course, restaurants, swimming pool, free Wi-Fi access and tennis. A location for weddings and special events with a full time, on-site wedding coordinator.
Nearby
Easton
City / town · 6 listings · 8 mi away
Kent Island
City / town · 15 listings · 12 mi away
Cambridge
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Chesapeake Beach
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Denton
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Rock Hall
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Prince Frederick
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Severna Park
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My experience
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