August 23, 2021

Plenty to See and Do in St. Michaels MD           

Katie and Gene Hamilton

Bring Binocular News

Savor the seafood, shops and maritime history on the Chesapeake 

Get a taste of Maryland’s eastern shore in Talbot County with a visit to St. Michaels, a former waterman’s town which has evolved into a popular retirement community.  We’ve lived in St. Michaels for many years and watched the town change slowly and thoughtfully hoping to balance the needs of locals and come-heres. The small town’s attention to boatings – sail and power – has long made it a popular cruising mid-Atlantic destination for boaters from Annapolis, the western shore, Baltimore and Philadelphia, all of them not far by water or land.

St Michaels MD is an eastern shore getaway with Chesapeake Bay Maritime Museum and lots of crabs.
St Michaels MD is an eastern shore getaway with the Chesapeake Bay Maritime Museum.

We’re like many cruisers who first visited St Michaels by boat and returned to settle there to eat crab, enjoy specialty shops and learn maritime history.

St Michaels
Great Shopping in St Michaels

As you enter town on Route 33, known as Talbot Street, you’re coming from the north and the heart of town is only 9 blocks long. In your drive through town you’ll pass specialty shops and restaurants and see a sign for the Classic Motor Museum with examples of pre and post WWII classic automobiles, vintage trucks and motorcycles in the Exhibit Barn. A large colorful map of town is displayed at the post office and further on at the Visitor Center to give you a sense of what you’ll find. Just follow the Parking signs, leave your car and walk or ride your bike around town.

Shoppers appreciate the eclectic collection of art galleries, antiques, clothing, furnishing and specialty stores. Jewelry lovers find an enduring collection at two fine jewelers in town.

The restaurants in the town of Saint Michaels cater to all budgets and palettes, many offering takeouts as well as indoor and outdoor seating. For breakfast try Carpenter’s Street Saloon, Crepes by the Bay and The Galley. Early risers and locals pick up their coffee at Blue Heron and Blue Crab in town or the Rise Up kiosh just outside of town. For lunch and dinner foodies find many eateries in town, and on the waterfront, the iconic Crab Claw still a favorite of visitors. In the center of town visit the St. Michaels Museum at  St. Mary’s Square, a charming old building that houses local history lore and artifacts.

Chesapeake Bay Maritime Museum

At the other end of town you’ll see the Chesapeake Bay Maritime Museum on Navy Point, known for its extensive collection of the Bay’s unique watercraft, shipbuilding and waterfowl. As you drive through town you’ll see its impressive entrance – the raised Tilghman Island draw bridge – leading to a large parking lot and numerous indoor and outdoor exhibits. The historic Hooper Strait Lighthouse sits proudly on the grounds overlooking the Miles River. The 44-foot wide hexagonal lighthouse had to be cut in half to move it on a barge to the museum; it is one of three remaining screw-pile lighthouses in the Chesapeake Bay. Walk up to the top and get a view of the harbor with binoculars. It’s a wonderful place to see the surrounding area and get a closer look at the boaters coming in and going out of the harbor. Here’s a few tips about Traveling with Binoculars.

CBMM is a popular weekend getaway and day trip destination known for its festivals celebrating seafood, wooden boat building, antique and classic boats, the July 4th fireworks, the Watermen’s rodeo boat docking contest and charity boat auction, just to name a few. The museum has the skipjack Rosie Parks and other visiting skipjacks throughout the summer.  

Today the town has visitors who arrive on the American Cruise Line, but for day visitors there are enjoyable Miles River cruises.  Step aboard Selina II, an elegantly restored gaff-rigged 42-foot long,16-foot beam cat boat built in 1926. Or take the Patriot cruise on a 65-foot passenger vessel with an enclosed and open air upper deck. Go aboard the historic 1920 buyboat Winnie Estelle at the museum. And there’s a Habor Shuttle and Love and Dreams, a pontoon tour boat. The town harbor is always busy with visiting boats along with kayaks and paddleboards.  Being on the water don’t forget binoculars to see the waterfowl along the shore and take a peak at the grounds of waterfront homes.

Free concerts in the park, log canoe races and festivals

In the summer months enjoy free concerts at the waterfront Muscrat Park on Thursday evenings. Later rest on the benches by the cannon and watch harbor activity or stargaze with binoculars. 

Or catch a race on the river of log canoes which are unique to the Chesapeake Bay. A log canoe is a work boat converted to a racing sailboat with hiking planks that allows the crew to use their body weight to keep the canoe upright.They are quite a site to see each with their own chase boats in case they tip over (which happens often.)

Wine and spirits lovers are drawn to establishments like St .Michaels Winery, the local maker of 18 wine styles with a quaint, year-round tasting room and Simpatico with Italian wine and food tasting.  Lyon Distillings is for rum lovers, a micro distillery dedicated to producing American rum from 100% Louisiana sugarcane and traditional pot stills. Did we mention craft beer? Eastern Shore Brewing, the oldest brewery on Maryland’s eastern shore celebrates 10 years in St. Michaels where you’ll find a nice selection of craft beer and a welcoming place to enjoy it in or outside. 

Weekend festivals including the annual Waterfowl Festival in Easton, bringing many visitors who spend the day to enjoy the activities, shopping and eating their way through town.  By night the dark skies offer free live night time entertainment – stars in all their splendor to gaze at. There’s plenty of traditional night life in the bars and restaurants in town but for those who enjoy a more quiet time, stargazing is entertaining and intriguing for everyone, especially kids.  One of the best viewing areas is at the end of Seymour Street where there’s a small park overlooking the open waters across the river. On a clear summer night you can sit on the park bench, raise your binoculars and witness a spectacular night sky. 

Take a daytime stroll or bike ride through the neighborhoods on both sides of Talbot Street to see the restored houses, many with little libraries to enjoy.  Go in either direction and see the intricate trim and lush gardens surrounded by picket fences.  Take a stroll or bike ride on the Covered Bridge Trail which you’ll find on Railroad Avenue at Bradley Park where you can enter the trail that parallels Route 33. The park is an open area with a gazebo and play equipment for little kids just a few blocks from Talbot Street. You’ll find two swing sets, a sandy play area, even porch style swings for adults with plenty of shady areas and bench seating. The trail runs 2.1 miles behind neighborhood houses, marshy areas and a back entrance to St. Luke’s United Methodist cemetery with many very old tombstones. You’ll get glimpses of Talbot Street but it’s mainly a quiet reprieve that runs to a parking lot at the entrance to town. From the covered bridge that spans the headwaters of Broad Creek’s San Domingo Creek look for Blue Herons and wood ducks who paddle beneath the bridge.

Our firsthand experience using binoculars when traveling: 8×25 compact binoculars are a good choice for traveling because they’re lightweight and easy to tuck into a backpack or purse. The first number”8” is its magnification which makes an image 8 times closer than what you see with your eyes; it’s good for a wider field of view. The “25” is the size of the objective lens measured in millimeters that defines how much light the binocs can gather. A larger objective lens has more light gathering power so the image resolution will be higher and brighter.                      

A short drive to Pickering Creek for bird and nature lovers

If you’re a birders or traveling with kids, take an easy 15 mile drive from the town of St. Michaels to Audubon’s Pickering Creek in Easton and walk the trails of hardwood forests and 75 acres of freshwater wetlands. The center is a 400-acre working farm with over a mile of shoreline on a tidal creek and cropland. For kids you’ll find a Children’s Trail and Imagination Garden and Herb Garden, both wonderful kid-friendly areas to explore.

Many overnight visitors stay at the St. Michaels Inn at the entrance to town, the St. Michaels Harbour Inn or one of many B&Bs in town. As you leave town heading toward Tilghman Island you’ll see Chesapeake Bay Landing, another locals’ favorite for seafood. You’ve seen just about everything there is to see when you get to the Inn at Perry Cabin, a lovely luxury oasis with its’ Links at Perry Cabin just beyond in the Martingham community.

St. Michaels bills itself as the “heart and soul of the Chesapeake Bay” and most people who have visited will agree.  To learn more about St. Michaels go to

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Gene and Katie Hamilton travel the U.S. extensively in search of a favorite place. They are members of the Outdoor Writers Association of America.
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