St. Michaels, MD

As we turned off Route 50 onto Route 322, I smiled.  It wouldn’t be long before we would be in St. Michaels, Maryland.

I have always enjoyed being by the water, whether it be an ocean (my top pick), river, or lake.  There is something so beautiful, calming, and peaceful about it. 

If you feel this way, too, you’ll love St. Michaels.  It’s one of the Eastern Shore’s most popular seaside destinations…and a new favorite of mine as well.

This past summer, I visited 3 different times and each time, I discovered new things to do and see.  

Now, its time for YOU to get to know this charming Maryland town.


map from dc to st. michaels md
Map of the route from DC to St. Michaels, MD

St. Michaels is just 2 short hours from Washington, DC, making it an ideal destination whether you want to visit for a day, a weekend, or longer.  

If you’re coming from the DC metro area, you will have to cross the Chesapeake Bay Bridge.  Before you leave, be sure to:
(1) Check the Bay Bridge traffic report, and
(2) Have enough cash or an EZ pass for the toll. Tolls are only collected one way: heading east on Route 50.  


In 1677, Christ Episcopal Church of St. Michael Archangel Parish was founded; the town then developed and grew around it. During the 1700s and 1800s, it was a thriving shipbuilding and seafood processing town.  To this day, it is still thriving, with tourism as one of the major contributors.

Christ Church, St. Michaels Parish
Christ Church, St. Michaels Parish

Christ Church is open for tours.  Friendly and knowledgeable docents are on site to answer questions and point out interesting features of this beautiful landmark. 

St. Michaels is also known as “The Town that Fooled the British” as a result of an event that took place in the early 1800s.  Here’s what happened:

“Early on the morning of August 10, 1813, a number of British barges sailed up the Miles River intending to shell the town and its harbor fort. The citizens of St. Michaels, having been warned in advance of the planned attack, had evacuated most of the women, children, livestock and valuable possessions to an area outside of town known as “Onion Hill.” A British landing party came ashore, and the defenders of the small battery at the mouth of the harbor fled into town. The British returned to their boats and shelled the town, while two artillery batteries returned fire from the shore of the harbor.

According to local legend, Brigadier General Perry Benson, commanding officer of the Talbot County militia, ordered lanterns placed in treetops just outside of the town and all other lights in the town extinguished, causing the British to overshoot the town. Among the few dwellings hit was a brick house near the harbor now known as the “Cannonball House.” Whether true or not, the story inspired the town’s moniker as “The Town That Fooled The British.” The British suffered two wounded men during their brief invasion, and the Americans reported “no injury to any human being.”

If you’re a history buff, be on the lookout for signs and placards posted throughout town sharing details about St. Michaels’  storied past. 


Bringing kids to St. Michaels with you?  Great!  There are several activities they’re sure to enjoy.  Even if you don’t have kids, you may find yourself getting back in touch with your “inner child.” 😉  


Chesapeake Bay Maritime Museum Campus Map

CBMM Campus Map
(Click on the map image to view an enlarged version)

The Chesapeake Bay Maritime Museum (CBMM) offers more than meets the eye.  The self-guided tour of the CBMM campus allows visitors to tour its 14 areas of interest at your own pace.

Visitors can explore the 1879 Hooper Strait Lighthouse; watch the shipmasters at work in the boatyard; check out the vessels in the Small Boat Shed and learn about the Maryland Crab Meat Company; watch live demonstrations by a real blacksmith; and much more. 

Chesapeake Bay Maritime Museum
The lighthouse at the Chesapeake Bay Maritime Museum


A Traveling Broad & her Dude in front of the Patriot Cruise boat
Me & my Dude in front of the Patriot Cruise boat

If you want to learn more about the area around St. Michaels, consider taking a Patriot Cruise along the Miles River.

Cruise options include:
Narrated Historic Cruises: This cruise lasts 1-1/4 hours and leaves daily at 12:30pm and 2:30pm (additional times offered on weekends)
Island Music Cocktail Cruises: This cruise lasts 90 minutes and leaves daily at 5:30pm.  A variety of music is featured on this cruise, but leans towards Reggae, creating a fun island feel. The ticket price includes 1 drink (beer, wine, rail drink or soda/bottled water).  No narration is included. 

Other Important Details: 
♦ Seating: There are 2 levels of seating: on the main level, which is enclosed and air-conditioned and on the upper deck, which is covered but open on the sides.
♦ Refreshments: Snacks and drinks (alcoholic and non-alcoholic) are available at the snack bar. 
♦ Restrooms: Separate men’s and women’s bathrooms are available on the main level.
Wheelchair Access: Cruises are accessible to wheelchair-bound passengers (unless its high tide).

You can also book cruises with one of several other companies operating in and around St. Michaels.


Shore Pedal & Paddle
Shore Pedal & Paddle

If you’d like to enjoy the outdoors during your visit, no problem.  There are a few places you can rent bikes, paddleboards, and kayaks.  This is a great way to get some exercise while you’re exploring St. Michaels from land or sea.


Hungry? Don’t worry.  No matter what you’re craving,  you can satisfy it at one of the many restaurants in town.  There is something to suit just about anyone’s palate.   

I really enjoyed the breakfast at the Carpenter Street Saloon.  The omelets, coffee, and service were top-notch and the prices were very reasonable (they also serve lunch and dinner).  Marco’s Café also has really affordable breakfast options and offers outdoor seating.  

Waterfront Dining

If you prefer to enjoy a view of the river while you’re dining, check out one of the waterfront restaurants.

We dined outside at Foxy’s and was able to hear live music playing in nearby Muskrat Park while I ate.  What an unexpected treat!

View from Foxy's Harbor Grill
View from Foxy’s Harbor Grill outdoor patio
the Crab Claw Restaurant
The Crab Claw Restaurant

We celebrated my birthday while we were in St. Michaels and enjoyed a delicious breakfast at Stars Restaurant at the Inn at Perry Cabin. 

Delicious Eggs Benedict at Star Restaurant
Delicious Eggs Benedict at Star Restaurant

⭐Fun Fact: The wedding reception scenes in the movie “Wedding Crashers” were filmed here.

The Inn at Perry Cabin
The Inn at Perry Cabin 


Whether you have a crazy sweet tooth or just crave a little something different, check out one of St. Michaels’ amazing specialty shops serving delectable treats.  

If you want sweets, stop in The Old Candy Shoppe.  It offers a wide variety of candy and creamy, delicious ice cream. 


One of the charming salespeople at the candy shop
One of the charming salespeople at
The Olde Candy Shoppe

For ice cream lovers, Justine’s is a must.  They have been around for more than 30 years and serve some of the most delicious homemade ice cream I’ve had the pleasure of tasting.   

Justine's Ice Cream
Justine’s Ice Cream – yummy!


In addition to the adult beverages available at the bars and restaurants throughout town, St. Michaels has a brewery, a distillery, and 2 wine tasting rooms all located in or near the Old Mill District.  Go, try, and buy if you like.    

Eastern Shore Brewing
Eastern Shore Brewing


Shopaholics and window shoppers alike will enjoy perusing the eclectic mix of shops in town that offer everything from clothing to souvenirs to unique gifts.


Whether you are alone, on a romantic getaway with your love, or with your family, lodging options are available in St. Michaels. 

There are a lot of charming B&Bs (bed and breakfasts), many in historic homes.  They are a little pricier than a typical hotel stay, but if you’re looking for a unique experience in a romantic setting, a B&B is the way to go.

Hotels are available as well and are probably a better option if you are bringing children.  Rentals such as Airbnb, Homeaway, etc. are available. 

If you are planning to visit during a particularly busy time, consider looking in nearby Tilghman Island or Easton if you can’t find a place to stay.  Both locations are just a few miles from town.


And last but definitely not least, St. Michaels is a great place to relax and unwind from the hectic pace of everyday life.  These views are amazing.  What more could you ask for?!  

Sunrise in St. Michaels, MD

Have you been to St. Michaels?  What did you like the best?  Where was your favorite place to eat, drink, stay, etc.?  Share in the Comments below ↓.

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