We’ve compiled a list of 20 great St. Michaels experiences not-to-miss.

1. Celebrate our Beautiful Harbor

While you’re in town, take your favorite person to brunch or cocktails on the water at one of St. Michaels’ waterfront restaurants, including Foxy’s Harbor Grille  or  The Crab Claw Restaurant. We have lots to do for a full weekend also, with fabulous found in so many places to eat and drink, along with all our unique shops, inns, and attractions.

2. Free the Foodie in You

Everything from great coffee shops and lunch spots, to local seafood and authentic Italian. St. Michaels has so many excellent restaurants, outdoor cafés, and bistros to free the foodie in you, we’ve gathered them up and listed them here. Don’t forget the St. Michaels Farmers Market, where you’ll find nothing but locally sourced foods and goodies. You can also check out top-reviewed St. Michaels restaurants on TripAdvisor to see what others are saying about their St. Michaels foodie experiences.

3. Maneuver the Miles River

See osprey, dolphin, and the area’s most magnificent historic estates with a narrated scenic river cruise aboard Patriot Cruises. You can also sail on Selina II, or rent a small craft, kayak or SUP board to explore the harbor and many of St. Michaels’ meandering creeks and waterways.

4. Art, Art, Baby!

The St. Michaels Art League is very active in the community, and St. Michaels also has wonderful artisan shops and art galleries, with events regularly scheduled.

5. Hot Crabs, Cold Beer

Need we say more? Hot steamed crabs, cold, locally crafted brew or your favorite ice-cold beer on draft. And if you like eating crab, but not picking them, our restaurants also feature crab cakes, fresh fish, and other foods too) Just add those waterfront views of St. Michaels harbor, and all that hip, historic St. Michaels charm, and you’ve got yourself an authentic, Chesapeake Bay experience right here.

6. Sensational Strolling & Shopping

When you mix our small town charm with wow-factor shops and more, you’ve got a day or weekend trip to make strolling St. Michaels sensational. Take a self-guided walking tour, taking in St. Michaels’ waterfront while the church bells are chiming, and the smell of steaming crabs wafts around you. Then, head up to Talbot Street and the surrounding areas for the most unique shops and friendly shop owners. You’ll be glad you’re here, because the whole town is happy to host you, with congenial spirits and friendly faces.

7. Take in a Foodie (or Drink) Fest

This is the BEST town for a party, and you can count on making memorable experiences at one of our foodie and drink festivals, including the March 2023 St. Michaels ChocolateFest; ; the early June St. Michaels Brewfest, and the late Octoaber OysterFest.

8. Exercise Your Body, Mind, Spirit

Take in the flattest, fastest 13.1 in the mid-Atlantic with the  St. Michaels Running Festival  and  Historic Drawbridge Half with other running events planned throughout the year. If running isn’t your thing, we have great bicycling on trails and along streets off of Talbot Street. And, now we have the new Perkins Family YMCA near the Bay Hundred Community Pool, along with spas, local yoga studios, and a new Pete Dye golf course. And for your spirit, be sure to take in the church bells each day from Christ Church St. Michaels, as you stroll our peaceful, walkable, friendly town.

9. Get Jolly, Mon!

With an Island Music Cocktail Cruise aboard Patriot Cruises. Enjoy the Miles River, for a fun, scenic cruise, with an onboard cash bar and a variety of music leaning towards Reggae played. This 90-minute cruise offered on most Saturdays from Memorial Day to Labor Day and also on the Sundays of Memorial Day, July 4th and Labor Day weekends.  And at 4pm before Memorial Day and after Labor Day on most Saturdays.

10. Yo, Ho, Ho, and a Bottle of Rum… or Beer, or Wine, or Olive Oil 🙂

Handcrafted right here in St. Michaels, you’ll find hand-crafted deliciousness in tasting rooms, with live music and more, and all within walking distance from one another at Windon Distilling Co. (Lyon Rum), Eastern Shore Brewing, St. Michaels Winery, and Great Shoals Cellars.

And don’t forget, Olivins Fine Olive Oil & Vinegars has wonderful tastings of olive oil, balsamics and other fine treats.

11. Tiptoe through the Tulips

Well… maybe more like through the daffodils n St. Michaels. St. Michaels is nationally recognized for its beautiful gardens and landscaping, and we can’t wait to share all the beauty with you.

12. Get Your Mermaid On

You’ll find coastal arts everywhere throughout the shops in St. Michaels, and we’re the location for the Eastern Shore Sea Glass and Coastal Arts Festival, and the Arts at Navy Point.

13. Watch Bailers and Boardsmen Sailing

The bailers keep the iconic Chesapeake Bay sailing log canoes above water, while the boardsmen do a balancing act tacking and jibing down the Miles River… You’ll only find these beautiful historic boats on four rivers in the entire world, and you can see them on display at CBMM, and watch the races and others sailing from aboard Patriot Cruises.

14. Sleep Like Royalty

Seriously. Whether staying overnight on your boat at a local marina or hotel, at a waterfront inn or B&B, or at one of St. Michaels’ beautiful vacation homes, you’ll wake up feeling refreshed and ready to experience St. Michaels in meaningful ways.

15. Experience History Unfolding

Experience history in the making as shipwrights transform wood and other raw materials to rebuild Maryland Dove, Maryland’s flagship and a replica of one of the ships that began the Maryland Colony in 1634. Construction is almost completed at the Chesapeake Bay Maritime Museum.  (And, there’s a great view of the ship from the decks of the Patriot.

16. Be Nostalgic

Our town has you taking in every bit of detail from the moment you arrive. And that’s especially true when it comes to exploring rich history. Take in our local history museums, antique shopping, the Antique & Classic Boat Festival, or the Classic Motor Museum, who host Cars & Coffee on Saturday mornings, and the Thanksgiving Parade of Classic Cars.

17. Slurp Some ‘Arsters

Oysters—or ‘arsters as the locals call them—are now available without the need for an “R” month, thanks to our booming, local aquaculture. Local restaurants serve oysters raw, steamed, Rockefeller, you name it. And don’t forget, OysterFest each October is a must to get your slurp on!

18.Tap Your Toes to Live Music

Enjoy waterfront concerts in Muskrat Park from June through September, with these free, Thursday night concerts sponsored by the St. Michaels Community Center. Plus, the area’s restaurants, breweries, wineries and bars regularly host live music performances, for an experience in St. Michaels that you’ll hold memories of for a lifetime. Favorite music spots include Carpenter Street Saloon, Foxy’s Harbor Grille, The Galley St. Michaels, Eastern Shore Brewing, and more.

19. Get Intimate

We’re talking getting to know St. Michaels better here… through beer and wine tastings, biking trails, and a great self-led walking tour. Plus, from historic inns and B&Bs, to marinas and vacation rentals, all the overnight accommodations in St. Michaels are exceptional.

20. Celebrate the Holidays

From celebrating with fireworks and Big Band Night for the Fourth of July, to a wonderful homes tour and parade as part of Christmas in St. Michaels, St. Michaels is the perfect backdrop for holiday celebrations throughout the year. St. Michaels is recognized as The Most Enchanting Christmastime Main Street In The Country. And don’t forget, Carpenter Street Saloon’s St. Patrick’s Day shopping cart races, a local tradition.