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Stroll past the lush resorts and swanky shops along the quaint main drag in St. Michaels, and you might never guess that for most of its life this town was a hard-working, hard-drinking place full of shipbuilders, watermen, crabpickers, and oyster shuckers.

Shipyards began to spring up hereabouts in the 1600s, more than a century before the town officially existed.By around 1800 there were half a dozen bigtime shipbuilding yards. The place was important enough that the British tried to take the town in 1813. They failed. The Cannonball House on Mulberry Street, one of more than a dozen National Register properties in town, got its name by taking a hit in that skirmish.

Hooper Strait Lighthouse at Chesapeake Bay Maritime MuseumSt. Michaels stayed true to its working class roots right on into the 1960s. The transformation began when the Chesapeake Bay Maritime Museum opened its doors in 1965. Within a couple of decades the town began popping up in some of the top-ten lists that the glossy travel magazines put together—most romantic getaways, best waterfront small towns, and the like.

St. Michaels deserves all of the tourism accolades it gets. Eating, shopping, strolling, sailing, events, atmosphere—the town is basically first rate in every category.Start with that maritime museum, which remains the town’s anchor attraction. Set on 18 acres right on a sweet stretch of Miles River waterfront, it has an entrance way framed by the old Knapps Narrows drawbridge. Inside, there is the gorgeous the 1879 Hooper Straights screwpile lighthouse, a working boatyard, and more than 100 historic vessels, including several log canoes and skipjacks that are listed on the National Register.

The exhibits on display in various buildings around campus are mostly top notch, focusing in on such topics as on oystering, the seafood packing industry, waterfowling, the watermen’s lifestyle, and more. Visitors can arrange to be an “Apprentice for a Day” in the boatyard, working under a professional shipwright to help restore an old boat. In the summer months, wooden kayaks, rowboats, and small sailboats are available for rental. From big band nights to oyster festivals and boat expos, the special events I’ve attended at the museum have been consistently excellent.

St. Michaels Downtown (JJP)Leaving the museum, head to your left on Talbot Street to make your way into the heart of downtown St. Michaels. From the volume of shops and restaurants, you’d never guess that the town’s population barely breaks the 1,000 mark. Tourism truly has transformed this place.

Be sure to bring your appetite. Bistro St. Michaels and 208 Talbot are the top rated fancy restaurants. The casual options I’d recommend are Eva’s Pizzeria & Wine Bar and the venerable Carpenter Street Saloon, where the stated goal is to be “the best dive bar, well, anywhere.” Be sure to stop in their fun little gift shop; it’s owned by a good friend of mine, Keith Graffius.

St. Michaels Downtown Christmas Parade (JJP)If you’re craving the classic Shore dining experience, the Crab Claw is a seafood joint that serves up steamed crabs on picnic tables set on a waterfront deck with a gorgeous view. And more good news is on the way for St. Michaels dining: A new seafood restaurant called Awful Arthur’s is slated to open soon. It will operate under the steady hand of veteran restaurateur and Eastern Shore of Virginia native Arthur Webb, another friend.

No daytrip to St. Michaels is complete without a stop at the gleaming Justine’s Ice Cream Parlor. Their specialty shakes have been written up in the New York Times, the Chicago Tribune, and Life Magazine, and elsewhere. Sweet-tooth types might also want to try the handmade chocolates at the St. Michaels Candy Company.

One last dining note: St. Michaels is thick with eateries, including a whole bunch of places that I haven’t been to yet. Just by wandering around you’ll run into lots of good options beyond the ones mentioned here.

On the shopping front, St. Michaels tends toward high-end women’s fashion and accessories, along with decorative items for the home. There are lots of art galleries, too. Check out Flamingo Flats, which is all specialty hot sauces and seasonings, and Simpatico, which is all Italian imports, from ceramics and jewelry to chocolates and wines. The last time the wife and I stopped in the excellent Calico Toys & Games, she dropped more than $150 restocking our inventory of gifts for kids.

Lyon Distilling Co. in St. MichaelsRight on the Talbot Street main drag you will also find a brewery, a winery, and a rum distillery. The tours that Lyon Distilling Company offers get rave reviews.

Getting out on the water while in St. Michaels is easy as can be. There are kayak rentals, big-boat tours, sailing charters, the aforementioned maritime museum small-craft rentals, and other options. Six or so times a year, there are log canoe races out on the Miles River, and you do not want to miss that only-in-the-Chesapeake affair if the timing works out. Check with the Miles River Yacht Club for the schedule.

St. Michaels is a town that can really keep a daytripper hopping, racing to and fro to try and fit everything in. Try to remember that this is also a prime town for aimless meandering. Over on the waterfront side gorgeous old houses line quaint residential streets. A couple of blocks the other way is the short and sweet St. Michaels Nature Trail, accessible off of Railroad Street, Grace Street, and Chew Avenue. Bands and musicians are featured frequently in little Muskrat Park, and maybe you will be lucky enough to be there when the St. Michaels Gospel Choir is singing.

In closing, a bit of trivia: For advance homework, you might want to watch “The Wedding Crashers” again. Most of it was filmed in nearby Easton, but there are scenes set in St. Michaels as well.

Harold Baines of St. MichaelsAnd more trivia: Keep an eye out for the guy pictured here. That’s former Orioles and White Sox star Harold Baines, a St. Michaels native who still makes his home here. I lived in Chicago back in the 1980s, and while there I could quite regularly be found chanting “Harold! Harold!” from the right field bleachers over his various hitting and fielding heroics.

And here are bonus Christmastime tips: St. Michaels puts on one of the Shore’s best Christmas parades. And halfway between St. Michaels and Easton along Route 333 there is a guy who puts up insanely fantastic holiday scenes in his yard featuring Santa in the midst of things like crashed airplanes and giant locomotives.

Here is the St. Michaels website. And here is the Talbot County website.

And here is what else is in the neighborhood:

• Tilghman Island is gorgeous. You can sail aboard the skipjack Rebecca T. Ruark there with a great Eastern Shore character, Captain Wade Murphy.• Take the ferry across the river to Oxford, another great destination for aimless strolling and waterfront views. By the way, that ferry service has been running since 1683, making it nation’s oldest commercial ferry operation.• There is lots to do in nearby Easton.

Written by Jim Duffy

NOTES: The lighthouse photo is courtesy of Maryland Tourism. The rum photo is courtesy of Lyon Distilling Company. The other photos here are by Jill Jasuta Photography.


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