23 Family Friendly Things to do in St Michaels, MD (2024)
I have lived in Maryland for over 10 years and so I consider myself an expert haha! I absolutely love St. Michaels, Maryland! It’s this incredibly charming town on the Eastern Shore of Maryland.
When you visit, you’ll immediately feel the rich history making it an ideal destination for you to explore. Trust me, the beautiful waterfront views, the seafood at local restaurants, and the one-of-a-kind shops and galleries make St. Michaels a place filled with so many delightful things to do.
It’s a spot that I’m sure you’ll thoroughly enjoy!
In this post, we’ll explore some of the top things to do in St. Michaels, so you can make the most of your visit.
Top 23 Family Attractions in St Michaels, MD
Whether you’re looking for outdoor activities such as kayaking and fishing or indoor options like visiting museums and art galleries, there’s lots of things to do in St. Michaels for everyone! Here are some great ideas!
1. Chesapeake Bay Maritime Museum
Chesapeake Bay Maritime Museum in St. Michaels, Maryland, is dedicated to preserving the maritime heritage of the Chesapeake Bay region and offers visitors a wealth of exhibits and activities to enjoy.
The museum has several galleries that cover a wide range of topics. Your kids will love the interactive exhibits in the Touch Tank gallery, where they can learn about the animals that live in the Bay. The boat building workshop is a popular attraction, allowing you to see how boats are made.
You can also enjoy riding on the museum’s steamboat, the Choptank. This boat offers cruises around the St. Michaels harbor and gives you a chance to learn more about the history and ecology of Chesapeake Bay.
The Chesapeake Bay Maritime Museum is a great day trip to St. Michaels, MD from Baltimore for kids of all ages and will provide a fun and educational experience.
Pro tip: Be sure to visit the building with all the maps of the Chesapeake Bay. Also, plan to spend several hours here in order to fully explore everything.
2. Sail Selina II
Sail Selina is an ideal option for you if you have always desired to experience sailing on a luxurious yacht and is among the top Chesapeake Bay boat tours for sailing aficionados seeking an adventure. Situated in the charming St. Michaels Harbour Inn and Marina, you have the option to either participate in sailing or enjoy the stunning Eastern Shore scenery.
The Selina II yacht is a stunning vessel with mahogany cabinetry and polished brass accessories that exude elegance and can accommodate up to six guests. The two-hour Chesapeake Bay boat tour, led by Captain Iris and her team, departs from the Harbour Inn and Marina, passing by the Chesapeake Bay Maritime Museum, and heading to the Miles River.
Sail Selina tour also provides you with a chance to spot incredible wildlife such as Bald Eagles, Osprey, and porpoises. Captain Iris provides a personalized tour of St. Michaels waterfront, highlighting the history of the Selina II yacht and its adventurous past.
Additionally, Sail Selina offers romantic 2-hour Chesapeake Bay Champagne Sunset Sail cruises that are perfect for special occasions like marriage proposals and wedding anniversary celebrations.
You get to be treated to a wide variety of sunset refreshments, including champagne, pinot grigio, Shiraz, un-oaked chardonnay, craft beer from leading Maryland artisanal breweries, and hors-d’oeuvres while watching the stunning sunset.
3. Visit Tilghman Island
Visiting Tilghman Island from St Michaels is a unique experience that you would always remember. Located on the Chesapeake Bay and a short drive from St Michaels, this small island offers stunning views of the water and wildlife in its natural habitat.
There are plenty of activities to enjoy here as well, such as fishing, kayaking, sailing and birdwatching. You can also take advantage of local attractions like museums and galleries or visit nearby towns for shopping and dining experiences. The island is known for its seafood, hospitality and boating opportunities.
4. Classic Motor Museum of St Michaels
The Classic Motor Museum of St. Michaels is a must-visit destination for automobile enthusiasts visiting the Eastern Shore. Located in a historic building in downtown St. Michaels, the museum features a stunning collection of classic and antique automobiles from various eras, including the early 1900s to the 1960s, pre and post WWII classic automobiles, muscle cars to European sports cars etc.
Visitors can admire these beautifully restored vehicles, which include iconic models such as the Ford Model T, Mustang, and Thunderbird, as well as other rare and unique automobiles. In addition to the cars on display, the museum also features various automotive memorabilia, including vintage gas pumps, license plates, and signs.
If you’re a lifelong car enthusiast or simply appreciate the artistry and engineering of classic automobiles, the Classic Motor Museum of St. Michaels is an absolute must-see.
Pro tip: It is not an all-day affair, but you could tie it with a visit to the Lyons distilling Company.
5. Go biking, kayaking and paddle-boarding with Shore Pedal & Paddle
If you’re looking to explore the beauty of St. Michaels in a fun and active way, Shore Pedal & Paddle is the perfect option for you.
This popular local attraction is the location to rent kayaks, paddleboards, bicycles and retail while in the area and thus allow visitors to bike and kayak through the stunning natural landscapes of the Eastern Shore.
Their launch area is also within walking distance from the shop so it’s easy to get your items and head out.
6. St. Michaels Winery
If you or your family members are Wine lovers visiting St. Michaels, you won’t want to miss a visit to the Saint Michaels Winery.
This charming winery offers visitors the chance to sample a variety of award-winning wine tastings, over 20 wines to choose from including reds, whites, and fruit wines made with locally sourced ingredients.
They have knowledgeable staff on hand to guide you through the selection and answer any questions you may have. If you are a wine lover, here are some more wineries you can check out in Annapolis, MD.
7. Oxford-Bellevue Ferry
The Oxford-Bellevue Ferry in St. Michaels Maryland is a charming and historical attraction that has captivated visitors for centuries.
A 20-minute round trip ferry located along the Miles River, it transports guests between Oxford and Bellevue, two of Talbot County’s oldest towns, across the scenic waters.
This state-owned ferry has been in operation since 1683 and is the oldest privately owned ferry in the United States. It can also accommodate vehicles, RVs, bicycles and more.
Pro tip: Avoid busy times or days because it only holds nine cars so you might be out of luck if you come and its full.
8. Oystering on the Chesapeake
Oystering on the Chesapeake Bay is a centuries-old tradition that has been a vital part of the Eastern Shore’s history and culture. And there’s no better place to experience this unique and exciting activity than in St. Michaels.
Several local companies offer oyster harvesting tours, giving visitors the chance to see firsthand how oysters are harvested and processed.
You’ll get to sample some of the freshest and most delicious oysters you’ve ever tasted, right there on the water.
9. Patriot Cruises
If you’re looking for a unique and memorable way to experience the charming town of St. Michaels, Maryland, look no further than Patriot Cruises. Set sail on the Miles River aboard one of their elegant vessels and take in the stunning views of the Chesapeake Bay, historic homes, and iconic lighthouses like the hooper strait lighthouse.
With knowledgeable and friendly crew members, you’ll also learn about the area’s rich history, the river and see why it’s a beloved destination for locals and visitors alike.
You can enjoy the 75-minute-long scenic tours and explore historic landmarks such as Tilghman Island or visit nearby attractions like Oxford-Bellevue Ferry Park or Navy Point Park. you might even catch a few dolphins come visit you while on your way into the harbor.
The prices are also quite reasonable for a great time making memories with your kids! They have a downstairs cabin which is air conditioned while the upstairs deck is shaded and both offer beautiful views.
10. Eastern Shore Brewing
Eastern Shore Brewing is the oldest brewery on the Eastern Shore of MD and is a craft brewery that is dedicated to bringing quality beer to locals and visitors alike. The brewery specializes in small batch beers, featuring unique flavors and ingredients not found at larger brewing companies.
They have ever-changing selection of brews on tap, as well as seasonal releases throughout the year. From IPAs to sours and stouts, their beers are sure to satisfy any palate! Their knowledgeable staff is always happy to guide you through their selection and share the stories behind each brew.
11. The Lyon Distilling Company
The Lyon Distilling Company is a craft distillery located on Maryland’s Eastern Shore. Founded in 2013, the company specializes in small batch spirits made from locally sourced ingredients. Their range of artisanal products includes whiskey, vodka, rum and gin – all of which are carefully crafted to bring out their unique flavor profiles.
With an emphasis on sustainability and environmental responsibility, the Lyon Distilling Company has become one of the leading producers of craft spirits in the United States.
12. Check out some St. Michaels foodie experiences
When it comes to dining options, there are no scarcity of choices in St. Michaels. Here are some top-reviewed St. Michaels restaurants and St. Michaels’ waterfront restaurants:
For a truly unique experience, head to Crab Claw Restaurant for an evening of waterfront dining. Here you’ll find some of the freshest seafood around, all prepared in their own secret recipes that you won’t find anywhere else.
The deck overlooking the harbor also makes it a great place to relax and enjoy your meal with a view. Some great choices are their award-winning crab cakes, oysters, clams and steamed crabs. This is one of our fave restaurants in St. Michaels, MD.
If you’d prefer something a bit more laid back, then be sure to stop by the Miles River Yacht Club. This restaurant is perfect for casual lunches and dinners with its outdoor seating area overlooking the harbor.
Here you can enjoy sandwiches, soups, salads and seafood dishes made from locally sourced ingredients. And with their cozy atmosphere and amazing view, it’s no wonder why this is one of the top places to eat in St. Michaels.
If you’re in the mood for authentic Italian cuisine, Limoncello Italian Restaurant and wine bar is the place to go. From homemade pasta dishes to fresh seafood, the menu is full of delicious options. The cozy atmosphere and extensive wine list make it the perfect spot for a romantic dinner or a night out with friends.
Craving pizza? Look no further than Ava’s Pizzeria and Wine bar, which serves up some of the best pies in town. With creative toppings like fig jam, prosciutto, and arugula, their pizzas are a cut above the rest. Pair your pie with a glass of wine from their impressive selection.
For a casual meal with a view, head to Foxy’s Harbor Grille. Located on the harbor, this laid-back spot offers a variety of burgers, sandwiches, and salads. The real star of the show, though, is the crab dip – a creamy, cheesy concoction that’s sure to be a hit.
For a fine dining experience, make a reservation at Stars Restaurant at the Inn at Perry Cabin. Located at the luxurious Inn at Perry Cabin, this upscale spot serves up seasonal, locally sourced dishes with an emphasis on seafood. The elegant atmosphere and impeccable service make it the perfect spot for a special occasion. The Inn at Perry cabin is also listed as one of our top recommendations of the best bed and breakfast in St. Michaels, MD.
Finally, if you’re looking for some delicious comfort food classics, be sure to check out the Harbour Inn Restaurant. This local favorite serves up classic dishes like burgers, sandwiches, and delicious homemade pies. Plus, their outdoor patio is a great place to relax while you enjoy your meal.
13. Go shopping
If you’re planning a visit, be sure to save some time for some shopping in St. Michaels, MD! This charming town is full of unique boutiques, galleries, and specialty shops. Here are a few places to check out:
If you’re a fan of handmade jewelry, don’t miss Ophiuroidea. This artisanal jewelry studio features one-of-a-kind pieces made with precious metals and gemstones. Owner and designer Danielle Joyner takes inspiration from the natural beauty of the Chesapeake Bay and creates pieces that are both elegant and unique.
The Chesapeake Trading Company, a quaint little shop sells home décor items, knick-knacks, and other unique items from the Eastern Shore.
Silver Linings is another artistic shop that sells sterling silver and gemstone jewelry.
Some other great options are:
- Guilford & Company
- Antiques on Talbot
- Downtown Easton
14. Foodie fest
Enjoy some amazing experiences eating, drinking and snacking.
There is the annual St. Michaels ChocolateFest on March 4th, 2023 which includes lots of restaurant chefs hooking up items to show dishes and desserts that are chocolate inspired.
Next, try out the St Michaels Brewfest on June 3rd, 2023, or the annual Italian wine and food festival at St Michaels or the OysterFest.
15. Enjoy some live music
There are lots of live music opportunities while in St. Michaels, MD especially through concerts, restaurants, breweries and more.
16. Enjoy some holiday celebrations
St. Michaels puts on some great holiday celebrations especially during the Christmas time. There is Christmas in St. Michaels event that is a sight to behold during the holiday season. It is also considered one of the best things to do in St. Michaels MD in December.
17. Sleep in a bed and breakfast
Sleeping in a bed and breakfast at St Michaels is an experience like no other. Located on Maryland’s Eastern Shore, this charming little town offers breathtaking views of the Chesapeake Bay, making it the perfect place to unwind and relax. With a variety of unique boutiques, restaurants, galleries and inns to choose from, St Michaels is the perfect destination for a weekend getaway.
18. Kayaking tours
Kayaking in St. Michaels, Maryland is an incredible experience! With its beautiful and serene waters, the area offers some of the best kayaking tours around. Whether you’re a beginner or an experienced paddler looking for adventure, there are plenty of options to choose from.
Take a guided tour through the scenic creeks and rivers teeming with wildlife, or head out on your own for a more intimate exploration of this amazing landscape. For guided tours, you can check out Shore Pedal & Paddle.
For Kayak lovers, there are lots of adventurous spots in Maryland to go kayaking!
19. Biking tours
Biking tours in St. Michaels, Maryland is another exciting way to explore the Eastern Shore’s landscape. They provide an ideal opportunity for adventure seekers and nature lovers alike. Shore Pedal & Paddle also offers biking tours and kayaking tours.
20. Walking tours
When it comes to walking tours, you can never run out of options here. Check out the self-guided walking tours in St. Michaels, MD. Embark on a self-guided historical walking tour in St. Michaels, Maryland, stroll up to Talbot Street, and journey back in time to experience the rich heritage and culture of this quaint town.
While walking around, you’ll come across centuries-old homes, churches, and museums that showcase the town’s fascinating past. From the Chesapeake Bay Maritime Museum, where you can learn about the town’s fishing and boat-building industries, to the Cannonball House, which dates back to the War of 1812, there are endless opportunities to discover St. Michaels’ unique history.
The walking tour will also lead you through lush gardens and picturesque waterfronts, where you can take in the town’s natural beauty and tranquil atmosphere.
21. Bird and wildlife watching
Bird and wildlife watching in St Michaels, MD is an activity that is sure to delight nature lovers.
The Chesapeake Bay Estuary is a major bird migration route, making St Michaels the perfect spot for avid birdwatchers. Birders can observe hundreds of species throughout the year, including Bald Eagles, Red-tailed Hawks, Merlins, and Ospreys. In addition to these permanent residents, many migrant species also pass through, including warblers, flycatchers, shorebirds, and more.
In addition to bird watching, St Michaels is also home to a variety of wildlife. Large mammals such as deer and coyotes can often be spotted in the surrounding forests, while smaller ones like squirrels and rabbits make their homes among the trees.
22. Fishing
If you’re a fan of fishing, St. Michaels, Maryland, is a dream come true. Located on the shores of the Chesapeake Bay, the town offers an abundance of opportunities to reel in a catch. You can cast your line off the town’s many piers, docks, and beaches or head out on a charter boat or private charter with an experienced guide.
The waters are home to a variety of fish species, including striped bass, bluefish, and flounder, providing a challenge for anglers of all levels.
You can also check out some more spots to go fishing while in Maryland.
23. St. Michaels Museum
St. Michaels Museum is a must-see attraction for anyone interested in the rich history of Maryland’s Eastern Shore. Today, visitors can explore a fascinating collection of exhibits and artifacts that showcase the town’s maritime heritage. The museum offers walking tours that provide visitors with an opportunity to explore its rich heritage, as well as learn about its history and culture.
Led by knowledgeable and engaging docents, these tours take visitors on a journey through St. Michaels’ charming streets and alleyways, highlighting its colonial and maritime past.
Final thoughts on things to explore in St Michaels, MD
In conclusion, St. Michaels, MD, is a charming and historic town that offers visitors a wide range of things to see and do. Whether you’re interested in exploring the town’s maritime heritage, discovering its industrial past, or simply strolling along its streets and waterfront, there is something for everyone in St. Michaels. Also, check out some great places to rent boats in Maryland.
From the fascinating exhibits and walking tours offered by the St. Michaels Museum, to the hands-on experiences at the Historic Mill Complex, to the quaint shops, restaurants, and galleries that line the town’s streets, St. Michaels has it all. So, whether you’re planning a day trip or a longer stay, be sure to put St. Michaels on your list of must-visit destinations. You won’t be disappointed!
