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.
Quick Facts
📍 Location: Maryland’s Eastern Shore
🚗 Drive Time: About 2 hours from Washington, DC
⏰ Recommended Stay: Day trip or weekend getaway
🚶 Walkability: Excellent. Once you’re downtown, most attractions, shops, and restaurants are within walking distance.
💰 Budget: Moderate
✨ Perfect For: Couples, history lovers, waterfront enthusiasts, and anyone looking for a relaxing small-town escape.
Is St. Michaels Worth Visiting?
If you enjoy charming waterfront towns, fresh seafood, unique boutiques, maritime history, and a slower pace, I think you’ll love St. Michaels. It’s the kind of place where you can spend the day wandering without a strict itinerary and still discover something memorable around every corner.
If you’re looking for nonstop nightlife or major attractions, however, you may find St. Michaels a little too quiet. This is a destination best enjoyed by slowing down and soaking in the atmosphere.
Location
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:
- Check the Bay Bridge traffic report, and
- Have an EZ pass for the toll. Tolls are only collected one way: heading east on Route 50.
- If you don’t have an EZ pass, they’ll take a photo of your license plate and send you a bill in the mail later.
A car is the easiest way to reach St. Michaels, but once you’re downtown, you can comfortably explore most of the town on foot.
History
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 is open for tours. Friendly and knowledgeable docents are on site to answer questions and point out interesting features of this beautiful landmark.
One of the most fascinating stories in St. Michaels’ history dates back to 1813, when British ships sailed up the Miles River intending to attack the town. According to local legend, residents placed lanterns in nearby trees while darkening the town itself, tricking the British into firing too high. The clever deception gave St. Michaels its famous nickname: “The Town That Fooled the British.” Today, you can even visit the Cannonball House, one of the few buildings reportedly hit during the attack.
If you’re a history buff, be on the lookout for signs and placards posted throughout town sharing details about St. Michaels’ storied past.
Best Things to Do in St. Michaels
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.” 😉
Visit the Maritime Museum
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.
Take a Cruise Along the River
Me & my boyfriend 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 at an additional cost.
- 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.
Enjoy Some Outdoor Activities
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.
WHERE TO EAT IN ST. MICHAELS
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.
Despite its small size, St. Michaels has an impressive variety of dining options ranging from casual waterfront seafood spots to upscale restaurants perfect for a special occasion.
Breakfast
I really enjoyed my meal 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.
During one of our trips to St. Michaels, we celebrated my birthday. My boyfriend treated me to a delicious breakfast at Stars Restaurant at The Inn at Perry Cabin.
🎬 Fun Pop Culture Fact: Look famliar? Fans of the movie “Wedding Crashers” (starring Owen Wilson and Vince Vaughn) may recognize The Inn at Perry Cabin. Several of the wedding reception scenes were filmed at this beautiful waterfront property.
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 were able to hear live music playing in nearby Muskrat Park while I ate. What an unexpected treat – dinner and a show!
The Crab Claw Restaurant is another good spot with both waterfront views and covered seating so you can dine al fresco even if its raining.
Sweet Treats
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 enjoy sweets, stop in The Old Candy Shoppe. It offers a wide variety of candy and creamy, delicious ice cream.
Another favorite spot for ice cream lovers is Justine’s Ice Cream Parlour. This family-owned business has been serving their delicious homemade ice cream since 1987. I worked at Baskin-Robbins when I was young, but I have to say that Justine’s has some of the best ice cream I’ve had the pleasure of tasting.
Drink
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. I really enjoyed doing a wine tasting at St. Michael Winery (I also bought a few bottles to take home with me) and my boyfriend
Shop
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.
Where to Stay
Each time we visited, we stayed in a hotel just outside of downtown. It was a great way to save money while still being only a short drive from all of the attractions.
If you want to be able to walk everywhere, staying in the historic downtown is hard to beat. However, if you’re traveling on a budget or just want to save your money for food and experiences, don’t overlook nearby Easton, Oxford, or Tilghman Island, all of which are just a short drive away and can offer additional lodging options.
Future You Will Thank You
✔️ Wear comfortable walking shoes.
✔️ Book popular restaurants ahead of time during peak season.
✔️ Leave time to simply wander downtown—you’ll discover hidden courtyards, charming side streets, and waterfront views you won’t find on a map.
✔️ Don’t rush your visit. St. Michaels is best enjoyed slowly.
Unwind
One of my favorite things about St. Michaels is that it encourages you to slow down. Whether you’re watching sailboats drift across the harbor, enjoying an ice cream on a bench overlooking the water, or simply strolling through town, it’s the perfect place to escape the pace of everyday life.
Whether you’re planning a romantic weekend, a girlfriends’ getaway, or simply looking for a charming destination within easy driving distance, St. Michaels offers the perfect blend of history, waterfront beauty, great food, and small-town charm. It’s a place I find myself wanting to return to again and again—and I have a feeling you might, too.
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 ↓.
This was a very interesting post! Thanks so much.