Destination: St. Michaels Maryland

By July 13, 2022July 20th, 2022Dock, Explore

Boaters have fallen in love with St. Michaels, Maryland and its lively nautical personality. Nestled on Maryland’s Eastern Shore, the 300-year-old town is rich in historic charm, but with a refreshingly modern vibe. It’s also close to other popular destinations such as Easton and Oxford, and just a day trip to Washington, DC. St. Michaels is not simply a stop on the way, it’s a destination unto itself! It’s actually one of the best boating vacation spots on the Chesapeake.

Ready to chart your course to St. Michaels for a fun-filled vacation adventure for the whole crew? Here’s all you need to know.

Don’t let St. Michaels fool you!


To really appreciate this seaport town, you should know a bit of its inimitable history and cleaver early settlers. First, it’s known as “the town that fooled the British.” And there’s a good reason for it. Just before dawn on August 10th, 1813, British barges off the coast of St. Michaels planned to attack the town and its harbor fort.  But the people of St. Michaels caught wind of the impending attack and did something quite clever.  They hoisted lanterns high on the masts of their sailboats and in the tree tops. The lights so high above the actual town, caused the attacking British to overshoot the town completely. Well, almost. One house was hit by cannon fire. That sturdy house still stands today and is known as the “Cannonball House.”  Apparently, the cannon ball came through the roof and rolled down the stairs. You can check out the house when you go there. It’s on Mulberry Street, adjacent to St. Mary’s Square. Unfortunately, you can’t go in, it’s a private residence.

Things to do in St. Michaels


The list of things to do and enjoy in St. Michaels is a long one. But first, give yourself plenty of time to explore and meander through its unique artisan shops and enjoy the fresh local fare in its many restaurants along Talbot Street. If you get tired of exploring on foot, you can even rent a bike to ride around town, or rent a kayak and explore the scenic Miles River.

One of the main attractions in St. Michaels is the Chesapeake Bay Maritime Museum. You’ll not only find 18 acres of waterfront displays and interactive exhibits, but you’ll also find a packed calendar of events. Because there is more history than can be packed into only one museum, you should also stop by the St. Michaels Museum. It’s packed with exhibits telling the colorful history of the town and surrounding area.

You’ll have a well-stocked galley if you make your way to the St. Michaels Farmers Market in the municipal parking lot at 204 South Talbot Street. You will be inspired as you stroll past tables heaped with fresh produce, just-baked pies, hand-made soaps and crafts, and delicious treats to eat and drink.

St. Michaels is also recognized for its first-class wineries, breweries and distilleries. The St. Michaels Winery is a charming winery housed in an historic old mill. Conveniently located right next door is Eastern Shore Brewing – for those who prefer an expertly crafted tall cold one. And for those who also enjoy a hearty rum and whiskey, just around the corner is the Lyon Distilling Company.

For even more things to see and do, visit the St. Michaels website.

Where to dock near St. Michaels


Lowes Wharf Marina

Located on Maryland’s Eastern Shore of the Chesapeake Bay, between St. Michaels and Tilghman Island, is the Lowes Wharf Marina in Sherwood. Boaters love the island-like setting that makes this marina feel like a true oasis. Lowes Wharf offers a ton of amenities and activities, including charter fishing, crabbing, kayaking and bicycling excursions. Guests also enjoy the on-site beach volleyball set ups, cornhole, ring tosses, billiards and swimming on their private beach. Right on-site is “The Wharf,” a tiki bar and restaurant with live music, Keno, a full bar inside, an outside patio bar and fire pits. Last, but not least, Lowes Wharf has an adjoining inn for boaters and their guests looking to spend a night on land.

Queen Anne Marina

Off the beaten path, on Kent Island, is the Queen Anne Marina in Stevensville. This quiet and peaceful marina overlooks the beautiful Chesapeake Bay. Queen Anne’s boat slips are nestled back in the protective waters of Price’s Creek, making it an ideal spot for boaters seeking calm waters and an idyllic serenity. A full-service marina , Queen Anne offers a gas and diesel fuel dock, new state-of-the-art floating docks, a well-stocked Ship Store, electric and water hook ups, and a 20-ton travel lift.  Since the marina has direct and easy access to the Chesapeake Bay, boaters enjoy how convenient it is for a day out on the water. Plus, it’s Kent Island’s best kept secret for those who love to fish and want easy access to the best spots on the bay.

Kentmorr Marina

The Kentmorr Marina in Stevensville, is more than a marina, it’s a sportfisherman’s paradise right on the Chesapeake Bay. Visitors have easy access to prime fishing spots directly outside the channel, saving precious time and fuel. Kentmorr is a full-service marina providing year-round solutions for all of a boater’s maritime needs including gas, diesel, pump-out service and ice. It’s also known for its friendly, knowledgeable management personnel and service technicians. The marina provides guests with heated bathrooms, shower facilities, and complimentary WiFi, making it easy to stay connected while on the water. Guests also enjoy the other amenities at Kentmorr, like the restaurant, Caribbean style tiki bar, and beach access. And, of course, the beautiful sunsets in the Western sky.

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Jo Montgomery

Author Jo Montgomery

Jo is a lifelong boat lover and writer. She learned the ropes of boating on her family’s 36’ Carver at the Jersey (joy-see) shore. With over 30 years of writing under her belt, she delights in seeking out, and sharing, the things most important to fellow boating enthusiasts. Jo now lives in Connecticut, near the water she adores, with her husband, two children and large, hairy dog. She is over the moon to be part of the Snag-A-Slip crew!

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