Issue: From the Chesapeake Bay Magazine Archives
Destination: St. Michaels, MD

St. Michaels, Maryland waterfront St. Michaels, Maryland
Both boaters and landlubbers alike will find 
the charms of St. Michaels irresistible. [February 2011]

By Ann Levelle
Photographs by Scott Sullivan

One hundred degree heat and nearly 100 percent humidity was not going to keep the crowds away from the Chesapeake Bay Maritime Musuem during its annual Antique and Classic Boat Show. Know why? First, the museum is packed to its figurative gills with jaw-droppingly stunning classic boats. Second, this is St. Michaels--Chesapeake country's favorite destination--the town you keep going back to, no matter how many times you've been before. Case in point: My husband John and I, along with our friends Drew and Kinley Bray. The four of us had decided to come down to St. Michaels on the Saturday of last year's show since none of us had been there in ages, so this seemed like a perfect excuse for the adventure. And aside from the heat, it was. But that's the beauty of St. Michaels, really, heat seems to have no bearing on anyone's good times in this summer tourist haven. Both boaters and landlubbers alike find its charms irresistible despite what nature throws at them.  

We wandered the museum grounds gazing longingly at all the lustrous wooden Chris Crafts, Trumpys and Matthews on the hard and in the water. Every one of the boats--from tiny runabouts to 50-foot wooden yachts--has been painstakingly restored, woodwork gleaming from God only knows how many coats of varnish. We also strolled through the vendor area for a bit, grazing among the artwork, crafts and throngs of cool old boat parts and accessories. By the time we'd done the rounds of the show, we were all hot and hungry and were ready to go next door to the Crab Claw for a little lunch. We got a table in the blissfully cold dining room surprisingly fast, considering the crowd. Then we dined on a couple of baskets of clam strips and a dozen crabs for good measure. They were fantastic as always.

As we were walking back to the car, my cell phone rang: It was my old pal Annie calling from South Carolina.
   "Hey, whatcha doing?"
   "I'm down in St. Michaels, we went out for crabs and to the antique boat festival."
   "Sounds like fun! Where's St. Michaels?" she asked (I swear I'm not making this up).
   "Seriously? You grew up in Maryland and don't know where St. Michaels is?"
    "Um . . . guess not. So where is it and what's there?"
   "Well, it's on the Eastern Shore," I replied. "And it's a cool little boating town with lots of good restaurants and a huge maritime museum. It's a pretty fun place."
   "Oh," she said, sounding excited. "You want to take me there when I come up this week? We need to get a boat trip in when I visit, you know."
   "Done," I said, "We'll take a powerboat too, so we don't have to waste precious time sailing down."

Fast forward to Tuesday, another record-breaking hot and humid June day. The sky and water were an equally hazy blue-gray color, and the water was as flat as could be. I couldn't be happier to be zooming down the Bay in one of the Chesapeake Boating Club's Albin 28s with the wind in my hair. Annie was pretty excited too, since our last few outings had been during similar weather, but slinking along at five knots in a sailboat. In the Albin, though, we made it from Annapolis to St. Michaels in a delightfully short two hours, and were quite surprised when we rounded red "4" to find an enormous cruise ship docked at the maritime museum. We slowed to the requisite five knots and puttered toward town, admiring the Hooper Strait Lighthouse as we neared the museum. As cruise director, I also thought it prudent to swing through Fogg Cove to show Annie the Inn at Perry Cabin, where a good bit of the movie Wedding Crashers was shot. She was duly impressed, especially by the movie part. 

Back in the harbor we aimed for the telltale red roofs of St. Michaels Marina. The marina's tall flag staffs, bearing both Old Glory and the Union Jack were also visible between some of the larger boats docked at the fuel dock. Fortunately for me (lacking confidence in docking as I do), St. Michaels Marina has a lot of very big slips to accommodate the Bay's finest. So I had no trouble sliding the comparatively tiny Albin 28 into the basin and then to the spacious slip--and, equally important, to the awaiting friendly and very helpful dockhand. 

Anxious to get into town for some lunch, we kept things brief at the marina office and store. There we met owner Mike Morgan, who personally gave us a quick rundown on the marina, the WiFi, the pool, shower combos, etc.--and, perhaps hearing our stomachs growl, the lowdown on the three restaurants that surround the marina: St. Michaels Crab & Steak House, Town Dock Restaurant and Foxy's Marina Bar. And the mix of Old Glory and the Union Jack? What's that about? I asked. Ah, he said, that's a nod to the persistent old (and highly dubious) historical meme about St. Michaels, "the town that fooled the British" during the War of 1812.

Of course, Annie, who didn't even know where St. Michaels was, had no idea what he was talking about. So, as we began our short walk to town--all two blocks up Mulberry Street, that is--I expanded on Morgan's explanation, telling her that during the War of 1812 the British were poised to attack St. Michaels--which was a target because of its dozen or so shipbuilding facilities. The townspeople, in addition to chaining off the harbor entrance, lit lanterns in the trees far behind the actual town, causing the British gun ships to overshoot the town. The trouble with this legend, I told Annie, was that the actual attack happened well after dawn, which seriously undermines the whole lantern story. Not to mention that at least one house--that one in fact, I said, pointing to the so-called Cannonball House that we'd just passed on Mulberry Street--was actually hit and still has burn marks from the cannonball rolling down the stairs. (As it turned out, the Cannonball House was now up for sale, too . . . for a whopping $1,495,000. Later I found out that the house, built in 1805, sold in 1831 for $1,000. Ahh, inflation.)

Perry Cabin Annie wasn't exactly riveted by my brief history lesson--which was good, because not only had we reached St. Michaels' main drag, Talbot Street, but also, I was fresh out of history. For the moment, anyway. Since it was a Tuesday, the red brick sidewalks were pretty empty, but as we walked along, peering into shop windows, we saw quite a few browsers indoors. We had no trouble getting a table at the tiny Key Lime Cafe, a bright and airy restaurant with a very welcoming staff, housed in a tiny old cottage on Talbot Street. The menu, which changes regularly with the seasons and at the whim of the chef, was limited, featuring just a few appetizers, sandwiches and salads, but we each found something tasty. Honestly though, we'd have been quite happy with nothing but ice water, because it was furiously hot outside. Thankfully our waitress was excellent in her refilling duties and we had a couple of nice salads to hold us over for our afternoon of sightseeing.

After lunch we continued north on Talbot toward the maritime museum. Annie, obviously had never been there, and I, despite having visited the previous weekend, was more than happy to visit again since over the weekend I had focused solely on antique boats. Just inside the museum gate, docent Rick Green met us to give us the rundown of the marina exhibits. Volunteer docents are an important part of the Chesapeake Bay Maritime Museum experience, and Green was one of many enthusiastic guides we'd have throughout the day. 

We started our tour at the boatbuilding shed, where four shipwrights were hard at work on various wooden boats--a lapstrake skiff, an Adirondack fishing canoe and a duck canoe.

Volunteer docent Mary Sue Traynelis led us through the shop, explaining various planking methods to us (namely lapstrake vs. board-on-board). Then she showed us the painting room, while she explained the Apprentice For a Day program, in which anyone (kids, teens, whole families) can spend the day helping shipwrights build replicas of Bay boats--from Smith Island skiffs to canoes. Volunteers can choose to work for a single day, a weekend or any number of days throughout the 17-week boatbuilding process. She ushered us to one of the boats they had just finished building, which took a little more than 18 weeks to finish (due to lack of apprentices).

We bade Mary Sue good-bye and continued our tour around the museum grounds, visiting the lighthouse--and of course every air-conditioned exhibit we could find: the At Play on the Bay history exhibit, an art exhibit featuring watercolor master Marc Castelli [see Horton at Large, page 64], and a Holland Island history exhibit. We also managed to at least peer into the outdoor boat shed, the oystering building and the Waterman's Wharf, where you can try your hand at oyster tonging, eeling and catching crabs in a tank.

After a couple of hours, we figured we'd done our scholarly tourist duty at the museum and had earned ourselves a little time either with a frosty beverage or at the marina pool (or both). We didn't get halfway back to the marina, though, before a frosty beverage found us. A teen-age girl was handing out coupons to the Drink Shack, or, as the cutely painted sign on the sidewalk read, Drink Shack in da back. She pointed us between two gift shops to a tiny oasis where a man in a brightly painted building was selling fruit smoothies, fresh lemonade and virgin frozen pina coladas and daiquiris. Tiki umbrellas and tables were set up atop sand colored gravel and we enjoyed a couple of fresh smoothies in the shade--a true oasis on this hot and humid afternoon. We finished our beverages on the way back to the marina, where the small pool, nestled between the docks and the marina office/ship's store beckoned. 
   "So what do you think of St. Michaels?" I asked Annie as we lingered neck deep in the blissfully cold water. 
   "It's nice! I didn't expect there'd be this much to do in a tiny Eastern Shore town. I'm not sure we'll be able to cover it all in two days."

St Michaels boat fest My sentiments exactly. It had been a few years since I'd spent any extended time in town, and I'd forgotten how much there is to do here. At the risk of sounding like a tourist brochure (which, by the way if you need any, there's a tiny shack just south of the maritime museum entrance on Talbot Street that has hundreds of them available for the taking, including town maps and brochures on just about every attraction in town), St. Michaels really does have a bit of something for everyone. Boaters get some great marinas or a nice anchorage with only a short dinghy ride to town. And whether you come by land or sea, you get a world-class maritime museum--which is to say, all the Chesapeake history and culture you could want--plus tons of restaurants and shopping, a couple of excellent hotels, B&Bs galore, boating excursions and tours, and a dash of history. In case that wasn't enough, the town hosts a ton of town-wide events throughout the year that draw thousands of visitors to each--log canoe races, summer concert series, a fall festival, Christmas in St. Michaels, boat festivals and rendezvous, the list keeps on going. And with every visit you feel a little more a part of the tiny community that ties it all together.

Phew, okay brochure rant over. It was six in the evening and the day's heat finally started to let up. Annie and I waited until the bells at nearby Christ Church ended their evening concert, then headed back to the boat to clean up for dinner. We decided--wisely I might add--to eat at Town Dock restaurant, which backs up to the marina, since hefty storms were predicted and we wanted to leave the boat open as long as possible. The restaurant, which touts itself as casual fine dining, has outdoor patio tables, but given the heat and upcoming storms, we opted to dine on the indoor patio, which boasts huge windows and a great view of the marina and the harbor. 

Annie ordered excellent Panko fried oysters for an appetizer. By the time she (okay, we) finished these oh-so-plump oysters, we could hear the thunder rumbling in the distance. And about halfway through our dinners--shrimp scampi for Annie, and a delicious vegetable ravioli with a walnut cream pesto sauce for me--the increasing racket told us it was time to dash to the boat and button things up, so we could finish our dinner without worry. It was a heck of a storm and we sat for a good hour and drank our bottle of sauvignon blanc and watched the show. 

The next morning proved just as hot as the last, but not to worry--we had a day of mostly air-conditioned activities planned. We started out the day as I have started nearly every other day in St. Michaels--at Carpenter Street Saloon for breakfast. It's a no frills kind of place, but provides the kind of perfectly tasty and inexpensive breakfast that cures most any over-drinking issues and sets you up for a good day of sightseeing. And clearly it's the place to be in the morning, as the breakfast crowd was pretty decent even on a Wednesday.

We filled up on egg sandwiches and scrapple and such, then moved over to the saloon side of Carpenter Street to watch the U.S./Slovenia World Cup match on TV. For a good while it was just us and the bartender, but as the morning progressed, it became clear that tourists aren't the only clientele here at C-Street. By halftime in the game, the bar was hopping with local servers and bartenders from other restaurants who were all hanging out eating and gossiping (presumably before their lunch shifts started). Since we had a captive audience of locals at our service, we asked what we should do while we were in St. Mikes. Somewhat confused by the question, they only offered one reasonably straight answer: eat and drink. Then they mentioned the winery and brewery were both fun outings.

After the soccer match had ended we were ready to hit the town. Annie had insisted at some point during our visit we should eat crabs, so I decided now was the time, and off we went to the obvious place: the Crab Claw, the town's biggest crabhouse and arguably the most well known and popular on the entire Bay. Since we'd had a pretty hearty breakfast, we opted to order crabs by the piece (at a pretty good deal: $3 per crab), hush puppies and a pitcher of water. We happily picked our extra sweet and delicious half-dozen crabs on the covered patio while watching boats come and go in the harbor. It's the quietest I've ever seen the Crab Claw, I told Annie, noting that weekend nights the joint is all but throbbing, with people packed in like sardines. When our check came, I'd realized I'd made a classic rookie mistake--I'd forgotten to go to the ATM before lunch. Everyone who has ever been to St. Michaels and the Crab Claw knows that they don't take plastic here, and even though I'd been only four days before, it had totally slipped my mind. (Fortunately the restaurant has an ATM out front. I can only imagine the money that the owners of said machine make on fees.) 

Next up on our list of obligatory St. Michaels to-dos: shopping. We strolled Talbot Street, going into each blessedly cool shop and spending way more time in each than we normally would have. Thanks to the heat, we went into some artsy-crafty stores that normally wouldn't have interested us. I was pleasantly surprised at how few stores carried the cheesy stuff--St. Mikes T-shirt and crab magnets and such. We had made our way down Talbot Street in about an hour or so, and since we're not big shoppers, that had been ample time to browse. Now we had arrived at something a little more to our liking--the St. Michaels Winery.

We found the sign for the winery on the southern end of Talbot Street, and walked the block down Marengo Street to the tasting room, which is housed in the town's old mill complex. After we'd found a seat at one of several large round tables (perched atop old wine barrels), our pourer/server handed us menus and explained how their tasting system worked. You can pick wines a la carte or choose a "flight" of wines that the winery recommends you taste together. We chose the "staff favorites" flight, which included the winery's award-winners, dry whites and a couple of reds. The award-winnning Long Splice (delightfully dry and crisp), the pinot noir (smooth and creamy) and the Maryland Merlot (which tasted nothing like California merlots I've had) were my favorites. We also were able to taste a few all-Maryland wines, the grapes for which are grown at the winery's vineyard in nearby Wye Oak, Md., and the Martha Chambourcin, named after the Martha Lewis, which brings its varietals' grapes from a vineyard in Havre de Grace to St. Michaels each season. The winery, which opened in 2005, grows grapes at two Maryland locations, and  buys from other Maryland growers.  

After we finished off our wines, our very wine-literate servers packaged up our take-home souvenir wine glasses for us, and soon we were off for our next adventure: Eastern Shore Brewing! The brewery, which is just up Talbot Street from the winery, opened just two years ago but has already made a name for itself in the state. Three of their beers won medals in the Maryland Governor's Cup competition last October.

We sat at the bar of the sparsely decorated tasting room at the brewery and were met by a very tall, gregarious bartender with wild, dark curly hair and tattooed arms. I never got his name, but he immediately made us feel welcome. We ordered the flight of the day, which included all five beers on tap for the day--the Lighthaus Ale, a cherry brew, the Magic Hefeweizen, the St. Michaels Ale and the Knot So Pale Ale. We weren't particularly impressed by the first three, but the final two were fantastic brews. While we were sipping our beers, we chatted with the only other folks at the bar, who were coincidentally from Columbia, Md.--where Annie and I had both grown up. We also got a chance to meet the establishment's young brewmeister, a recent college grad who said they'd be brewing again the next day, and it would be another hot day at the office. The bartender translated for us. They only brew every few weeks, and the process is extremely hot. Also, you can tell when they're brewing because you can smell it throughout a several block radius (which is to say, all of St. Michaels).
Sufficiently buzzed from our wine and beer tasting adventures, we headed for the pool again. After an hour or so of lounging poolside we took showers and were ready to hit the town again. This time we were off to Ava's pizzeria and wine bar for dinner. We had been told by folks at Carpenter Street and the winery that Ava's had the best pizza in town, plus a great wine list and a ton of other good food. And right they all were. 

Ava's occupies a classic St. Michaels home along Talbot Street, and the dining rooms are in the front two rooms of the house and on the front and back porches. The eat-in bar area is also in one of the main front rooms. It was immediately evident to us that this was where the locals eat. We saw and overheard a lot of local business conversations, the bartender obviously knew a lot of the customers by name, and nobody but Annie was sunburned.

We perused the extensive wine list, finally ordering a bottle of pinot noir to accompany our garlic mussels appetizer. Then we moved on to Ava's homemade pizza, choosing prosciutto, baby portobello mushrooms and spinach from the list of gourmet toppings. The pizza was fantastic, with a crispy, thin crust and perfectly bubbly cheese. Ava's makes everything in-house (including potato chips), using many local ingredients, and it definitely shined through. 

While enjoying our great dinner, we discussed our trip. Annie liked St. Michaels, and agreed with the servers we had met at Carpenter Street that morning, that the best way to enjoy this town is to eat and drink. And we certainly had our fill of that. She also enjoyed the museum and crabhouse, which made her feel like she was at home in Chesapeake country. 

And despite my having been here plenty of times, I was reminded why boaters are constantly flocking here and so many return multiple times in a summer: It's comfortable to come to St. Michaels. You always know what's in store for you, and the more you come back, the more it grows on you.