WHY GO: Remember the reception scene from the Wedding Crashers where the boat glides by and you wonder how there could be a real place so fantastically picturesque? It was filmed in St Michaels MD, a Chesapeake Bay yachting town known for its superior Maritime Museum, charming main street shops, and yes, THAT VIEW.
Oh – and lately – there’s a growing interest in Frederick Douglass’s connection to the town. The Getaway Mavens know all about the very best things to do in Saint Michaels Maryland for curious romantics. So, start planning here.
Naturally, all three are listed in our 18 Romantic Getaways in Maryland.
Things to do in St Michaels MD
VISIT: Chesapeake Bay Maritime Museum
The town of St Michaels Maryland, like almost every other Chesapeake town, was built on the oyster industry. In fact, the very Chesapeake Bay Maritime Museum itself was built atop oyster shells, as this was the site of an oyster canning plant.
The Museum is a fount of information about the Drowned River, an alternate name for the Chesapeake, because, as the original river filled with tidal water, it spread to create the wide, mostly shallow body of water it is today; with troughs in the center over 150 feet deep.
Through a myriad of buildings on 18 acres, programs and demonstrations, it does an excellent job immersing visitors in the Chesapeake’s boating and fishing history and culture. A premier destination attraction in Maryland, plan on at least a half day to explore.
Learn About Oysters “Big as Forearms”
Back in the 1600’s, when Pocahontas was saving John Smith’s life (or not: sorry, Disney fans, historians highly doubt Smith’s account), Chesapeake Bay oysters were as large as forearms.
In the 18th into the 19th Century, “Bugeyes” – easy-to-sail dredge boats – dominated the bay. With oysters piled high, watermen met up with “Buy Boats,” and Buy Boats sold to processing plants where oysters were shucked and crabs “picked.”
These were all links in a chain of work that was arduous, physically demanding, and male oriented. But colorblind. Black and white men toiled together as Maryland was home to the largest number of free slaves, even before the Civil War.
Discover the Reasons for Oyster Mania Post-Civil War
Oyster experts cite the Civil War as a turning point in the Oyster Industry. Cans of oysters, cheap and readily available, were shipped to the front lines, rendering these bivalves a staple of both Union and Confederate mess supplies.
Soldiers soon developed a taste for the slimy shellfish, so, upon returning home, no matter how far from the sea, they sought out this delicacy. Oyster Bar Restaurants popped up all over the country to fill demand. These establishments were so in vogue in the 1880’s, there were 200 in New York City alone.
Spend Time “Oystering” in the Chesapeake Building
Enter the Oystering on the Chesapeake Building to board a model of an oyster boat that, through clever audio and video, gives you a good idea of what it felt like (and still feels like) onboard. As technology improved from tongs to automatic dredgers, it allowed for the gleaning of oysters from ever-deeper depths.
Be Amazed by the Number of Oyster Processing Companies That Existed In the 1800’s
Among exhibits that cover the oyster industry from harvesting to canning is one of the most unique displays: cans upon cans of oysters – with different labels representing dozens of companies – stacked ceiling high.
Continuing on with the shellfish theme, visit the Small Boat Shed and Maryland Crabmeat Company building, where you’ll find a re-created interior of a crab picking plant and a collection of fisheries’ boats.
Explore The 1879 Hooper Strait Lighthouse
The museum maintains the 1879 Hooper Strait Lighthouse where visitors can wander through homey rooms and climb upstairs to the lens. Unique to the Chesapeake Bay, the Screw Pile Lighthouse seems positively alien to someone used to the Saltshakers of New England.
The muddy bottom of the Chesapeake presented a challenge to lighthouse builders. Traditional structures tended to topple. So engineers came up with a way to literally “Screw” eight iron legs deep into the mud, with a platform on top to support a keepers cottage topped by a light.
Watch Wooden Boats Being Built In Real Time
Though the Working Boatyard runs a one year Professional Apprentice program, visitors can sign up to learn the rudiments of boat building in a short one-day class. Whether you choose to build a boat or not, it’s fun to climb the stairs to an observation gallery and watch the action taking place below.
Walk Precariously Out to the Oyster/Crab Shanty and Go Crabbing
If you’ve been to Tangier Island, the Watermen’s Wharf exhibit will look very familiar. Typical of a crab/oyster shanty, it’s a favorite with kids who can try their hand at crabbing from the dock.
Revel in Views of Chesapeake Bay and Miles River By Boat
What’s your preference: motor or sail? If motor, jump aboard a Patriot Cruise boat (next door to Crab Claw), from the Maritime Museum. If sail, the restored 1926 Selina ii, docked at Harbour Inn & Marina, is your perfect match. Both offer day, sunset, and themed cruises on some of the most picturesque seascapes in America.
TASTE: Lyon Distilling
Take a sip of “smoky” dark rum, corn and malt whiskey at this innovative Lyon Distilling.
TASTE: Eastern Shore Brewing
Try Situation Critical (West Coast style IPA), 12 Gauge (American Stout) and other year round and seasonal brews at the festive Eastern Shore Brewing.
WALK: Down Talbot Street To Shop, Stop, and Sip
Peruse the many stores and art galleries – not a franchise among them. Stop into St. Michaels Winery for a taste. And, if you have time and it’s open, stop into the St Michaels Museum – a tiny taste of town in a cornflower yellow cottage.
DRIVE: Frederick Douglass Driving Tour #3
This drive takes you to the outskirts of St. Michaels, where Douglass, treated abhorrently, resolves to self-liberate.
Stops include the site of his punishment, when, as a young teen, he was sent into the forest in back of what is now St. Johns United Methodist Church, behind a team of unbroken oxen for a cord of wood, and Lowe’s Wharf, from which Haddaway’s Ferry ran to and from Annapolis, bringing mail and news of the wider world.
One more remnant from Douglass’s childhood remains, closer to town, inside the Chesapeake Bay Maritime Museum property. Eliza Bailey Mitchell was Frederick’s closest-in-age sibling, and you can actually tour her modest whitewashed home as part of the museum.
Where to Eat in St. Michaels
EAT: Ava’s Pizzeria
This cute little pizza place is the local go-to for those who don’t want yet another seafood meal. Catering to the local community, it’s open all year – and HAS TO be good. Go on Mondays when pizzas are sold two for one – a bargain. As a pizza snob (from Connecticut in the NYC area), I was stunned by the quality of Ava’s pies – brick-oven crispy, chewy, and gooey, and yummy as all get out.
EAT: Ruse at the Wildset
To say that Ruse has made a splash in this seafood town would be an understatement. Tweaks on traditional have won accolades from both locals and visitors – some who were just waiting for a hip place like this to open. The raw bar is stocked with oysters from Washington (the state) to Maine, but even fish averse folks will find something – gnocchi, fancy burger, duck, pasta, etc. – here.
EAT: Locals Love
St. Michaels is a tourist town, with tourist spots aplenty. Where will you find the locals? At Chesapeake Landing (for steamed crabs). Both Bistro St Michaels and Plates @ 208 Talbot for great upscale Bay Cuisine; crab cakes). And at Carpenter Street Saloon (decent grub and “best Bloody Mary on the Eastern Shore”).
Where to Stay in St Michaels MD
STAY: Wildset, St. Michaels
On St Michaels’ Main Street, next to an antique shop and across from a gluten-free bakery, Wildset is nowhere near set in the wild. But who cares, when this relatively new inn, opened in mid-2021, is undeniably Zen-ish: with nature hued rooms that puts one in mind of a Scandinavian spa. In colors of hemp and eggshell, in linen and wood, with bedding so plush you can disappear into it – this is indulgence at its most elemental.
Family owned, this spot was formerly the Five Gables Inn. Now, several homes, built in the 1800’s, are completely renovated – with 15 rooms in the main building, and 19 room in two across the street.
First Impressions of Wildset
Wildset put you smack in the middle of shops on Main St. St. Michaels, where parking in the summer is nearly impossible.
Park (free!) in an ample lot beside the main house and walk in to a small gift-shop slash reception desk. Check in is swift and friendly and oh so chill. You’ll get an overview of amenities – most associated with high-end lodgings.
During the day, grab a bicycle from the rack out back, and toodle around the backroads of Talbot County. In the evening, pick up a complimentary s’mores kit and join fellow guest around the fire-pit for a bit of campfire fun.
Rooms at Wildset
Generously sized rooms are islands of tranquility, with soft, cloud-like bedding that lulls you into, what’s been for many of us, an unfamiliar feeling of peacefulness.
Rooms are equipped with blond hardwood floors; high, half-cathedral ceiling; a non-working (for now) wood stove/fireplace; and flat screen TV.
Bathrooms are nothing like those of even new hotels these days. Here, square, poured concrete sinks and walls plastered with hand-made tiles prove that designers went organic in the most eye-catching ways.
Breakfast at Wildset
Continental breakfast is grab and go – with coffee, yogurt, homemade granola, and amazingly flaky, fresh authentically French croissants.
STAY: Inn at Perry Cabin
Sounds rustic, but far from it. Owen Wilson and Vince Vaughn met their lady-loves right on the back lawn of the sprawling impressive, luxury Inn at Perry Cabin compound, in the movie Wedding Crashers. (Some Inn employees were actually enlisted as extras for the movie)
Rooms in pale colors, traditional colonial furniture with high-end bedding, are lovely, and service is friendly, low-key and on the mark. Some lavish chambers are even pet-friendly. It’s the perfect location to explore the Chesapeake Bay Maritime Museum right next door.
The Wildset and Inn at Perry Cabin are so romantic, we included them on our Best Romantic Hotels in Maryland post.