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17 Exciting Things to Do in St. Michaels, MD That You’ll Never Forget



St. Michaels, Maryland is a beautiful haven away from the hustle and bustle of city life. It’s the perfect charming city for day trips and week-long vacations alike. The small-town colonial feel will bring you back into a simpler, more peaceful time. There are many exciting and wonderful things to do in St. Michaels, MD while you visit. These include visiting historic sites, staying in charming inns, touring exquisite museums, as well as enjoying some delicious local cuisine. The next time you’re looking for a peaceful getaway, you should definitely consider St. Michaels as your destination. Here is a list of 15 sublime things to do in St. Michaels, MD once you arrive.

Photo credit: Mike Druckenbrod via Flickr

Shopping the Exquisite Boutiques and Fine Art Galleries

St. Michaels offers a lot of unique stores for the adventurous shopper. From antique stores to art galleries to upscale clothing boutiques and a variety of other treasures, you won’t be disappointed in the shopping possibilities.

St. Michaels Candy Co | Photo credit: Karen Mallonee


This antique store focuses a lot on nautical themed antiques, but also includes a variety of furniture, oyster plates, sterling silver, and so much more. This is definitely a quaint place for the traveler who loves to go antiquing.

2. Olivins

Olivins is a healthy food boutique featuring balsamic reductions, olive oils, and coffee among other items. Bill Acosta opened Olivins to provide the area of St. Michaels to have the best products for those with a picky palette. There is a variety of olive oils to choose from as well as syrups, honey, and so much more.

3. Ophiuroidea “The O”

This boutique markets to the unique East Coast culture and fashion. They feature women’s clothing, children’s clothing, sea glass, artisan jewelry, coastal decor and a variety of other unique gifts.

Enjoy Local Cuisine at These Restaurants

St. Michaels offers some of the best local East Coast cuisines with local Maryland flavors. Taking in these restaurants among the Victorian decor, you’ll be embarking on of the best things to do in St. Michaels, MD.

Bistro St. Michaels|Photo credit: Richard Quinn via Flickr

4. Awful Arthur’s Seafood Company

Awful Arthur’s Seafood Company has the only authentic oyster bar in all of St. Michaels. Here you’ll find fresh seafood, burgers, steaks, and chicken. This restaurant has a unique East Coast vibe that offers inside and outside dining.

5. Bistro St. Michaels

This restaurant has an upscale setting inside of a beautiful and quaint building. The cuisine offered is a mixture of American and French but blended in with a local East Coast influence.

6. Carpenter St. Saloon

This saloon is a St. Michaels staple. Actually, it’s become a tradition. Here you can get the coldest draft brews in the area and enjoy local live music.

7. Crab N Que

Now, this is the place where you can get local Maryland crab. You can also get some of the best local barbecue. From craft brews to top-shelf spirits, there is also plenty to drink and enjoy. It also serves family meals and unique rubs.

8. Foxy’s Harbor Grille

Foxy’s Harbor Grille is located in the middle of St. Michaels Harbor. Foxy’s serves tropical-infused mixed drinks, frozen drinks, craft beer, as well as grilled and steamed dishes. This is definitely a fun place to eat and take in the St. Michaels culture.

Explore the Magnificent Museums

There are a variety of museums in St. Michaels that offer an authentic maritime experience. The exhibits are featured indoors as well as outdoors in unique settings.

Hooper Strait Lighthouse, now a part of the Chesapeake Bay Maritime Museum in St. Michaels.
Hooper Strait Lighthouse

9. Chesapeake Bay Maritime Museum

On the waterfront, this is a unique museum that is completely authentic as well. It features the photogenic Hooper Strait Lighthouse. There are a plethora of exhibits featured indoors as well as outdoors.

10. Classic Motor Museum of St. Michaels

Classic cars abound at this amazing museum. Take a trip back in time and explore historical automobiles completely restored and on display for your pleasure. This museum is the perfect place to bring a car enthusiast.

11. Tilghman Watermen’s Museum

The Tilghman Watermen’s Museum is a very unique place to experience the history and culture of Tilghman Island. They include exhibits of tools of the trades, oral histories, as well as a variety of works by regional artists.

Enjoy the Beautiful Atlantic Coast

The Eastern coastline is full of charming Colonial and Victorian homes and gorgeous marinas. There are multiple ways to get around St. Michaels, and the best is by water. Take a tour, taxi, or admire the sunsets, if you’re looking for the absolute best things to do in St. Michaels, MD.

Patriot Cruises Narrated Historical Cruises. Escape to St. Michaels on the Eastern Shore of Maryland.
Photo credit: Dick McLeish via Flickr

12. Chesapeake Skipjack Sailing Tours

Aboard the historic Skipjack H.M. Krentz, you’ll be taken on tours of St. Michaels and it’s points of charm along the coast. Skipjack has a maximum capacity of 32 passengers. So, there is plenty of space to explore the boat and enjoy the serene experience. You can catch oysters, take in the gorgeous sunset, as well as learn history all during one cruise.

13. Lady Patty Classic Yacht Charters

Come aboard a 1935 racing yacht for a two-hour cruise around the Chesapeake Bay. This is another excellent cruise to take in the beautiful St. Michaels sunsets. You can reserve the yacht for private parties, group events, or even bachelor/bachelorette parties.

14. Oxford Bellevue Ferry

Established in 1683, the ferry holds nine vehicles, numerous bicycles, motorcycles, as well as passengers. The ferry provides shuttle service across the Tred Avon River every day from 9 a.m. until sunset. This is one of the coolest and most historical things to do in St. Michaels, MD.

15. Patriot Cruises

This is a 149 passenger boat that provides perhaps the most authentic tours around St. Michaels and the coastline. They provide a historical narration as they tour the area and explore the sights.

16. Sail Selena II

If you’re looking for something a bit more intimate. With a maximum capacity of 6 people, the upscale Selina II offers 2-hour sailings daily plus romantic champagne sunset cruises, sailing lessons, private charters as well as unique wedding experiences.

17. St. Michaels Harbor Shuttle/Water Taxi & Tours

This is an on-demand taxi service to take you all over the bay to different locations in St. Michaels. They also offer private and personalized tours of the harbor. The tour lasts approximately 30 minutes as it takes passengers around the maritime museums, charming real estate, and exquisite restaurants.

Photo credit: Mike Keller via Flickr

St. Michaels definitely should be on your radar the next time you plan on getting away. It’s close enough to many large East Coast cities for weekend getaways or fun day trips. But, it’s also worth visiting for longer if you’re coming from farther away because there are many wonderful things to do in St. Michaels, MD.

John Ghost is a professional writer and SEO director. He graduated from Arizona State University with a BA in English (Writing, Rhetorics, and Literacies). As he prepares for graduate school to become an English professor, he writes weird fiction, plays his guitars, and enjoys spending time with his wife and daughters. He lives in the Valley of the Sun.