Discovering The 23 Best Things to do in St. Michaels MD

Looking for the best things to do in St. Michaels MD? This charming waterfront town, located on the Eastern Shore of Maryland, is known for its rich history and quaint atmosphere. It’s a great destination for travelers looking to explore the area. St. Michaels is the beating heart of Maryland’s Eastern Shore, nestled on the Chesapeake Bay.

It has an individual spirit deeply rooted in maritime history, making it a fascinating place to visit. This town, just an hour and a half drive from Washington, D.C., is both a languid small town full of charm and a bustling vacation spot, especially in the summer. Rich in history, St.

Michaels was founded way back in 1677 and proudly earned its nickname as “the town that fooled the British” during the War of 1812. Of course, it’s also famous for its Maryland crabs, available from April through November.

During your time in St. Michaels, you can enjoy a variety of activities, including fishing, boating, sailing, historical or cocktail cruises, shopping, kayaking, biking, or simply relaxing around a pool with a good book. This town is hip, historic, and incredibly laid-back. It’s also known for being very pet-friendly, reflecting the community’s love for animals.

Filled with bustling marinas, fabulous restaurants, and one-of-a-kind boutiques, St. Michaels is a destination well worth a visit. With its beautiful waterfront views, delicious seafood restaurants, unique shops, and galleries, St. Michaels is teeming with activities sure to delight any visitor.

In this guide, we’ll delve into some of the top things to do in St. Michaels MD, ensuring you make the most of your visit to this idyllic town. Whether you’re interested in outdoor activities like kayaking and fishing or indoor options such as visiting museums and art galleries, there’s something for everyone in St. Michaels. 

If you’re looking for the best place to go crabbing in Maryland, you’ll be delighted to discover that the Chesapeake Bay offers an abundance of prime crabbing spots, making it a must-visit destination for seafood enthusiasts and outdoor enthusiasts alike.

Here are the 23 best things to do in St. Michaels MD:

1. Chesapeake Bay Maritime Museum

One of the best things to do in St. Michaels MD, is to explore the Chesapeake Bay Maritime Museum, which is dedicated to preserving the maritime heritage of the Chesapeake Bay region. This museum offers a plethora of exhibits and activities to enjoy. Inside, you’ll discover several galleries that delve into a wide range of captivating topics.

For families with children, the Touch Tank gallery is a must-visit, where kids can engage with interactive exhibits and learn about the fascinating creatures that call the Bay home. Additionally, the museum’s boat building workshop is a popular attraction, providing visitors with the opportunity to witness the craft of boat construction.

Families can also embark on an enriching journey aboard the Choptank, the museum’s very own steamboat. This charming vessel offers relaxing cruises around St. Michaels’ picturesque harbor, allowing passengers to delve into the history and ecology of Chesapeake Bay. 

2. Sail Selina II

Sail Selina presents an exceptional opportunity for those longing to experience the luxury of sailing on a yacht, making it a top choice among Chesapeake Bay boat tours for adventure-seeking sailing enthusiasts. Nestled in the picturesque St. Michaels Harbour Inn and Marina, guests can opt for a sailing adventure or simply savor the breathtaking views of the Eastern Shore.

The Selina II yacht, a magnificent vessel adorned with mahogany cabinetry and gleaming brass accents that exude opulence, can comfortably accommodate up to six guests. Led by Captain Iris and her dedicated team, the two-hour Chesapeake Bay boat tour sets sail from the Harbour Inn and Marina, passing by notable landmarks like the Chesapeake Bay Maritime Museum before heading towards the Miles River. 

During the Sail Selina tour, you’ll have the chance to spot remarkable wildlife, including Bald Eagles, Osprey, and playful porpoises. Captain Iris provides an engaging, personalized tour of St. Michaels’ waterfront, highlighting the storied history of the Selina II yacht and its adventurous past.

Furthermore, Sail Selina offers romantic two-hour Chesapeake Bay Champagne Sunset Sail cruises, perfect for marking special occasions such as marriage proposals and wedding anniversaries. Guests can indulge in a diverse array of sunset refreshments, including champagne, pinot grigio, Shiraz, un-oaked chardonnay, craft beer from renowned Maryland artisanal breweries, and delectable hors-d’oeuvres while basking in the breathtaking sunset view.

3. Visit Tilghman Island

Exploring the best things to do in St. Michaels MD, a visit to Tilghman Island is an unforgettable and distinctive experience. Situated along the Chesapeake Bay and just a short drive away from St. Michaels, this quaint island boasts breathtaking vistas of the bay and its abundant wildlife in their natural habitat. Tilghman Island offers a wealth of engaging activities, including fishing, kayaking, sailing, and birdwatching.

Furthermore, you have the opportunity to immerse yourself in local culture by exploring museums and galleries or venturing to neighboring towns for exceptional shopping and dining experiences. Renowned for its seafood, warm hospitality, and excellent boating prospects, this island is a hidden gem in the St. Michaels area.

4. Classic Motor Museum of St Michaels

For auto aficionados exploring the Eastern Shore, a visit to the Classic Motor Museum of St. Michaels is an essential stop. Housed within a historic downtown St. Michaels building, this museum showcases an impressive assortment of classic and antique cars spanning multiple decades, encompassing the early 1900s through the 1960s. 

This collection includes pre and post-WWII classics, muscle cars, European sports cars, and more. Enthusiasts can marvel at these meticulously restored vehicles, featuring iconic names like the Ford Model T, Mustang, Thunderbird, and a host of other rare and exceptional automobiles. Alongside the cars, the museum also exhibits a diverse array of automotive memorabilia, including vintage gas pumps, license plates, and signage.

Whether you’re a lifelong car enthusiast or simply appreciate the craftsmanship and innovation behind classic cars, a visit to the Classic Motor Museum of St. Michaels is an absolute must. A helpful tip: While it won’t consume your entire day, consider pairing it with a visit to the Lyons Distilling Company for a well-rounded experience.

5. Go biking, kayaking and paddle-boarding with Shore Pedal & Paddle

One of the best things to do in St. Michaels MD, is to immerse yourself in the beauty of the area through an exciting and active experience offered by Shore Pedal & Paddle. This renowned local attraction provides visitors with the opportunity to rent kayaks, paddleboards, and bicycles, making it the ideal choice for those seeking adventure. 

It allows you to explore the breathtaking natural landscapes of the Eastern Shore by biking and kayaking. Additionally, their convenient launch area is just a short walk away from the shop, ensuring a seamless start to your outdoor exploration.

When it comes to enjoying the bountiful delights of summer, few activities rival the joy of strawberry picking, and Maryland boasts some of the best strawberry picking farms in the entire region, offering a delightful and wholesome experience for families and fruit enthusiasts alike.

6. St. Michaels Winery

For those with a passion for wine exploring St. Michaels, a visit to the Saint Michaels Winery is an absolute must. This delightful winery provides a delightful opportunity to indulge in a diverse range of award-winning wine tastings, boasting a selection of over 20 wines that encompass reds, whites, and fruit wines crafted from locally sourced ingredients. 

The winery is staffed by experts ready to assist you in navigating the options and addressing any inquiries you might have. If you have a fondness for wine, you’ll also find additional wineries worth exploring in the Annapolis, MD, area.

7. Oxford-Bellevue Ferry

One of the best things to do in St. Michaels MD, is to experience the Oxford-Bellevue Ferry. Situated along the picturesque Miles River, this historic attraction has been enchanting visitors for centuries. Offering a 20-minute round trip voyage, it seamlessly connects the charming towns of Oxford and Bellevue, both steeped in Talbot County’s rich history. 

Remarkably, this state-owned ferry, in operation since 1683, proudly holds the title of the oldest privately owned ferry in the United States. Furthermore, it’s versatile, capable of accommodating vehicles, RVs, bicycles, and more, making it an essential part of any St. Michaels adventure.

8. Oystering on the Chesapeake

Exploring the timeless tradition of oystering on the Chesapeake Bay is an integral aspect of the Eastern Shore’s heritage and way of life, spanning centuries. When it comes to immersing yourself in this distinctive and thrilling endeavor, St. Michaels stands as an unparalleled destination. 

Numerous local enterprises provide oyster harvesting excursions, granting visitors the unique opportunity to witness the entire process of oyster collection and preparation up close. As an added treat, you’ll have the chance to savor some of the freshest and most delectable oysters imaginable, all enjoyed right by the water’s edge.

9. Patriot Cruises

Discover the best things to do in St. Michaels MD by embarking on an unforgettable adventure with Patriot Cruises. Experience the charm of this town as you set sail on the Miles River aboard one of their elegant vessels. Marvel at the Chesapeake Bay’s breathtaking vistas, historic residences, and iconic lighthouses like the Hooper Strait Lighthouse. 

Their friendly and knowledgeable crew members will regale you with tales of the area’s rich history, providing insights into why it’s a cherished destination for both locals and tourists. Opt for their 75-minute scenic tours, where you can explore historic landmarks such as Tilghman Island or pay a visit to nearby attractions like Oxford-Bellevue Ferry Park and Navy Point Park. 

Keep an eye out for playful dolphins that might grace you with their presence as you enter the harbor. Patriot Cruises offers reasonable prices, making it a perfect opportunity to create cherished memories with your kids. Plus, they have a comfortably air-conditioned downstairs cabin and a shaded upstairs deck, both offering stunning views of the surroundings.

10. Eastern Shore Brewing

Discover the best things to do in St. Michaels MD, including a visit to Eastern Shore Brewing, the oldest brewery on the Eastern Shore of Maryland. This craft brewery is committed to providing top-quality beer to both locals and tourists.

It’s renowned for its small batch beers, which boast distinctive flavors and ingredients not typically found at larger brewing establishments. Eastern Shore Brewing offers a constantly changing array of brews on tap, along with seasonal releases throughout the year.

Whether you’re a fan of IPAs, sours, or stouts, their diverse beer selection is bound to delight every taste preference. Their friendly and knowledgeable staff is always eager to assist you in exploring their beer offerings and sharing the fascinating stories behind each brew.

If you’re looking for a fun-filled day of indoor excitement for your little ones, you won’t want to miss out on discovering the best indoor playground in Maryland, a haven of adventure and entertainment that promises hours of joy for kids of all ages.

11. The Lyon Distilling Company

One of the best things to do in St. Michaels MD, is to visit the Lyon Distilling Company. Situated on Maryland’s Eastern Shore and established in 2013, this craft distillery excels in creating small batch spirits using locally sourced ingredients. 

Their exceptional lineup comprises whiskey, vodka, rum, and gin, each meticulously crafted to showcase its distinct flavor characteristics. Notably, Lyon Distilling Company places a strong focus on sustainability and environmental stewardship, making it a prominent player in the realm of craft spirits production in the United States.

12. Check out some St. Michaels foodie experiences

When it comes to dining options, St. Michaels offers a plethora of choices. Here are some highly-rated restaurants in St. Michaels, including waterfront dining options: For a truly unique dining experience, consider visiting the Crab Claw Restaurant. Nestled along the waterfront, it offers some of the freshest seafood in town, prepared using their exclusive secret recipes.

The deck overlooking the harbor provides a delightful setting to savor your meal with scenic views. Don’t miss their award-winning crab cakes, oysters, clams, and steamed crabs. It’s undoubtedly one of our favorite dining establishments in St. Michaels, MD. If you’re seeking a more relaxed atmosphere, don’t miss the Miles River Yacht Club.

This restaurant is ideal for casual lunches and dinners, boasting outdoor seating overlooking the harbor. Here, you can relish sandwiches, soups, salads, and seafood dishes crafted from locally sourced ingredients. Its cozy ambiance and breathtaking views make it a top dining destination in St. Michaels.

Craving authentic Italian cuisine? Limoncello Italian Restaurant and wine bar is the place to be. With a menu brimming with homemade pasta dishes and fresh seafood, it’s a haven for food enthusiasts. Its intimate setting and extensive wine selection make it perfect for romantic dinners or gatherings with friends. For pizza aficionados, Ava’s Pizzeria and Wine Bar serves some of the town’s finest pies.

Featuring creative toppings like fig jam, prosciutto, and arugula, their pizzas stand out. Complement your pizza with a glass of wine from their impressive selection. For a laid-back meal with a view, head to Foxy’s Harbor Grille, located on the harborfront. This relaxed spot offers a variety of burgers, sandwiches, and salads. However, the star of the show is their crab dip, a creamy and cheesy delight.

Seeking a fine dining experience? Secure a reservation at Stars Restaurant at the Inn at Perry Cabin. Situated at the luxurious Inn at Perry Cabin, this upscale restaurant showcases seasonal, locally sourced dishes with a focus on seafood. Its elegant ambiance and impeccable service make it an ideal choice for special occasions.

The Inn at Perry Cabin also ranks among our top recommendations for the best bed and breakfasts in St. Michaels, MD. If you’re in the mood for comforting classics, don’t miss the Harbour Inn Restaurant. This beloved local eatery serves up traditional dishes like burgers, sandwiches, and delectable homemade pies. Plus, their outdoor patio offers a delightful spot to unwind while enjoying your meal.

13. Go shopping 

When exploring the best things to do in St. Michaels MD, make sure to allocate some time for an enjoyable shopping experience. This picturesque town boasts a plethora of charming boutiques, galleries, and specialty shops. Here are a few noteworthy recommendations: If you have an affinity for handmade jewelry, Ophiuroidea is a must-visit.

This artisanal jewelry studio showcases exclusive pieces crafted from precious metals and gemstones. Danielle Joyner, the owner and designer, draws inspiration from the Chesapeake Bay’s natural beauty, resulting in jewelry that is both sophisticated and unique. For a delightful selection of home decor, knick-knacks, and other distinctive Eastern Shore items, explore the offerings at the Chesapeake Trading Company.

Silver Linings is another artistic boutique featuring sterling silver and gemstone jewelry. Additionally, you’ll find excellent shopping options at Guilford & Company, Antiques on Talbot, and Downtown Easton.

14. Foodie fest

Indulge in remarkable culinary experiences encompassing dining, beverages, and delectable snacks. Mark your calendar for the upcoming events: Don’t miss the annual St. Michaels ChocolateFest, where renowned restaurant chefs unite to present chocolate-inspired dishes and desserts that are sure to tantalize your taste buds.

For beer enthusiasts, the St. Michaels Brewfest  is a must-attend. Additionally, explore the annual Italian wine and food festival in St. Michaels or savor the flavors of the sea at OysterFest.

15. Enjoy some live music

When considering the best things to do in St. Michaels MD, immerse yourself in a vibrant live music scene that offers numerous enticing opportunities. Whether you’re seeking musical enjoyment at concerts, dining establishments, breweries, or various other venues, St. Michaels has you covered. 

Delight in live performances that range from local bands setting the ambiance at charming waterfront restaurants to dynamic concerts showcasing diverse musical genres. Explore the rich musical tapestry that adds a melodious touch to your St. Michaels experience, making it an unforgettable visit for music enthusiasts.

When exploring the diverse and vibrant state of Virginia, you’ll discover an array of enticing attractions and activities that showcase the best things to do in Virginia, from exploring historic landmarks in Williamsburg to savoring the natural beauty of Shenandoah National Park and indulging in the rich culinary scene of Richmond.

16. Enjoy some holiday celebrations

St. Michaels, MD, truly shines during the holiday season with its outstanding Christmas celebrations. The “Christmas in St. Michaels” event is a must-see spectacle, and it’s widely acclaimed as one of the best things to do in St. Michaels MD in December.

This festive occasion transforms the town into a winter wonderland, with beautifully decorated streets and a warm, welcoming atmosphere. In addition to the Christmas festivities, you can explore charming boutiques for unique holiday gifts, savor delicious seasonal treats at local eateries, and take a scenic stroll along the waterfront to admire the dazzling holiday lights.

Don’t forget to visit the Chesapeake Bay Maritime Museum, which often hosts special holiday exhibitions and activities. Whether you’re a local resident or a visitor, experiencing Christmas in St. Michaels is an enchanting way to celebrate the holiday season in this picturesque Maryland town.

17. Sleep in a bed and breakfast

Staying at a bed and breakfast in St. Michaels offers an unparalleled experience. Nestled on Maryland’s Eastern Shore, this quaint town provides guests with awe-inspiring vistas of the Chesapeake Bay, creating an idyllic setting for rest and rejuvenation. The town’s array of distinctive boutiques, restaurants, galleries, and inns beckons travelers seeking a memorable weekend escape.

While in St. Michaels, you can explore its rich maritime history at the Chesapeake Bay Maritime Museum, embark on scenic cruises along the bay, or indulge in delectable seafood dishes at waterfront restaurants.

For nature enthusiasts, the town’s picturesque parks and nature trails provide excellent opportunities for outdoor adventures. Whether you’re seeking relaxation, culture, or outdoor exploration, St. Michaels is the quintessential destination for a diverse and delightful getaway.

18. Kayaking tours

Exploring St. Michaels, Maryland, through kayaking is an extraordinary adventure, ranking among the best things to do in St. Michaels MD. This picturesque region boasts serene waters and stands out as a premier destination for kayaking excursions. Regardless of your skill level, whether you’re a novice or an experienced paddler seeking thrills, the options are abundant.

You can opt for guided tours, expertly led through the breathtaking creeks and rivers that host a diverse range of wildlife. Alternatively, if you prefer a more intimate experience, set out on your own to discover this remarkable landscape. For those interested in guided kayaking tours, Shore Pedal & Paddle is a reputable choice, ensuring you make the most of your aquatic adventure in this beautiful Maryland locale.

19. Biking tours

Engaging in biking tours in St. Michaels, Maryland, stands out as one of the best things to do in St. Michaels MD. It presents an exhilarating means to discover the captivating Eastern Shore scenery.

These tours cater to both thrill-seekers and nature enthusiasts, allowing you to immerse yourself in the area’s natural beauty and rich history. Shore Pedal & Paddle, a renowned local provider, not only offers exceptional kayaking tours but also extends its expertise to biking adventures.

Whether you’re exploring the town’s charming streets or venturing further into the pristine landscapes surrounding St. Michaels, these biking tours provide an active and immersive way to experience the area’s unique charm. So, gear up and pedal your way through the scenic wonders of St. Michaels, Maryland, for an unforgettable outdoor escapade.

20. Walking tours

When it comes to exploring St. Michaels, MD on foot, you’ll find an abundance of options to choose from. Consider embarking on self-guided walking tours within this charming town. As you venture on a historical self-guided walk through St. Michaels, Maryland, you’ll be transported back in time as you amble along Talbot Street, immersing yourself in the town’s rich heritage and culture.

While meandering through the streets, you’ll encounter centuries-old homes, churches, and museums that vividly depict the town’s captivating past. From the enlightening Chesapeake Bay Maritime Museum, shedding light on the town’s fishing and boat-building industries, to the historic Cannonball House, harkening back to the War of 1812, St. Michaels offers endless opportunities to delve into its distinctive history.

Additionally, these walking tours will lead you through lush gardens and idyllic waterfronts, allowing you to soak in the town’s natural beauty and tranquil atmosphere, making it a comprehensive and enriching way to explore St. Michaels’ unique history and scenery.

When exploring Salem, NH, you’ll find a myriad of exciting attractions and activities to make the most of your visit; from delving into the town’s rich history at the Salem Historical Society to savoring delectable local cuisine at the town’s finest restaurants, this charming New England destination offers a diverse range of the best things to do in Salem, NH.

21. Bird and wildlife watching

Engaging in bird and wildlife watching in St. Michaels, MD, is undoubtedly one of the best things to do in St. Michaels MD, especially for nature enthusiasts. Situated along the Chesapeake Bay Estuary, this area serves as a significant bird migration route, making St. Michaels a haven for avid birdwatchers. 

Throughout the year, birders can revel in the opportunity to observe a diverse array of species, which may include magnificent creatures like Bald Eagles, Red-tailed Hawks, Merlins, and Ospreys. Not only do permanent resident birds inhabit this region, but it also becomes a temporary home to various migrant species such as warblers, flycatchers, and shorebirds. 

St. Michaels’ natural charm extends beyond bird watching, as the area hosts a wide variety of wildlife. While exploring the lush forests surrounding the town, you might encounter larger mammals like deer and coyotes, while smaller creatures like squirrels and rabbits make their homes amid the trees, enhancing the allure of this destination for wildlife enthusiasts

22. Fishing

When it comes to the best things to do in St. Michaels MD, fishing enthusiasts will find their paradise. Nestled along the Chesapeake Bay’s scenic shores, this charming town offers an array of fantastic fishing experiences. Whether you prefer to cast your line from one of the town’s numerous piers, docks, or serene beaches, or embark on an adventure aboard a charter boat guided by seasoned experts, St. Michaels delivers. 

These waters are teeming with diverse fish species, including striped bass, bluefish, and flounder, catering to anglers of all skill levels. While exploring Maryland, be sure to explore other prime fishing spots as well.

23. St. Michaels museum

For those intrigued by the storied history of Maryland’s Eastern Shore, the St. Michaels Museum stands as an essential visit. Presently, guests have the chance to delve into a captivating assortment of displays and historical items, all illuminating the maritime legacy of the town. 

Additionally, the museum presents guided walking excursions, led by enthusiastic and well-informed docents, which grant visitors the opportunity to uncover the town’s rich heritage, while gaining insights into its history and culture. These immersive tours weave through the enchanting streets and alleyways of St. Michaels, shedding light on its colonial and maritime heritage.

When planning your trip to Lenox, MA, be sure to check out our comprehensive guide to discover the best things to do in Lenox, MA, from exploring the picturesque landscapes of Tanglewood and hiking in Kennedy Park to immersing yourself in the vibrant cultural scene at the Norman Rockwell Museum and savoring gourmet delights at the town’s top-notch restaurants.

Final Thoughts

If you’re searching for the best things to do in St. Michaels MD, you’ve uncovered a treasure trove of experiences waiting to be explored in this charming waterfront haven. From its storied history to the captivating maritime heritage, St. Michaels offers a blend of relaxation and adventure that few destinations can match.

Whether you’re savoring the delectable Maryland crabs, embarking on a nautical adventure, or strolling through its pet-friendly streets, this town encapsulates the essence of a perfect getaway. So, don’t miss the chance to soak in the beauty of St. Michaels, with its picturesque waterfront views, mouthwatering seafood, and a world of activities that promise unforgettable memories. Plan your visit today and discover why St. Michaels MD truly stands out as one of the best things to do in St. Michaels MD.