Falling for St. Michael's

48 hours of colonial charm and autumnal activity in Maryland's seaside resort town

Packing the car early on a Friday afternoon and driving north on Route 13 through the rural and rustic small towns of the Eastern Shore almost always indicates I am venturing to the Northeast to visit my New Jersey family for the weekend. Today, however, my husband and I had a modified mission, sparked by our need for a different sort of fall getaway and a craving for fresh seafood—think oysters. Lots of oysters.
Our destination is St. Michaels, Md., a historic seaside village on Maryland’s Eastern Shore about four hours north of Hampton Roads. The port of St. Michaels sits between the Miles River to the north and Michener’s Broad Creek to the south, and while the economic focus has shifted from the shipbuilding and fish processing days of the 1800s to tourism, maritime activity is still very much a part of the culture for this idyllic water world’s residents and visitors.

We picked an early November weekend to discover what modern St. Michaels has to offer mainly because the Chesapeake Bay Maritime Museum is hosting the annual OysterFest, part of Fall Into St. Michaels, a monthlong celebration boasting a flurry of seasonal activity.

FRIDAY, 6:30 P.M.
It’s dark when we arrive at Talbot Street, the main drag in St. Michaels, but even with limited visibility I can already tell I am going to love lingering here for a few days and begin to get excited about the prospect of meandering down cute and colonial streets.

We easily locate the Five Gables Inn and Spa, our bed and breakfast selection, and on first glance it is as quaint and cozylooking as I expected. What’s harder to gauge from the outside of the 19th-century home is that besides the well appointed guest rooms and lounge areas, the inn also houses an indoor pool, sauna, steam room and Aveda spa. We find our accommodations in the main guest house but learn that a total of 20 rooms are located in a total of three historic buildings.

Though I could readily cuddle up by the fire with a glass of wine and call it a night, my stomach has other plans, and we head down Talbot Street—Five Gables is within strolling distance of plenty of restaurant and shopping options—to seek out some sustenance. We can’t resist the aromas emanating from Ava’s Pizzeria and Wine Bar and quickly decide on our first meal. Despite finding much more than pizza and wine inside, after chatting up some locals at the bar who were well versed with the menu, we opt to split a signature wood-fired pie that did not disappoint. And of course, yearning for a small taste of what was to come, we are eager to finish with a plate of juicy oysters on the half shell sent over by our new friends. (As you might expect, the St. Michaels natives are very friendly.)


In the light of day, I find Talbot just as charming and only slightly more bustling. Homes and churches dating to the late 1700s line the tight street. Autumnal decorations adorn lampposts, shop owners place water bowls outside for canine companions, and several local organizations set up tables on street corners, selling fresh oysters and Creole seasoned fish to raise money for their causes. A crisp breeze blows in from the water, but the sunlight combats the need to sport anything other than a cushy sweater while popping in and out of the gift shops.

We approach St. Michaels Winery, also on Talbot, and pause for a tasting of some of their nautical-themed (of course) vintages. The Martha Chambourcin stands out with a soft feel, spicy notes and grapes that journeyed down the Chesapeake Bay from Havre de Grace, Md. And lucky for us, the sampling does not stop here. We discover Eastern Shore Brewing right next door and settle in at the bar for a few sips of their on-tap offerings.

All these libations have provoked our appetites, and I’m thankful it’s just about time for the day’s main event.

St. Michael’s OysterFest is as much about education as it is about eating. Sponsored by the Chesapeake Bay Maritime Museum, we take the opportunity to tour the 10 exhibit buildings, 125-year-old Hooper Straight Lighthouse, working boat yard and the world’s largest collection of traditional Bay vessels. The entire waterfront campus spans 18 acres, and today, activity fills every inch of it.

We watch some children take part in an oyster tonging competition and listen to an aquaculture and restoration lesson before making our way to the cookingdemonstration tent to make sure we secure a seat and a sample of a succulent clam fritter prepared by one of St. Michaels’ acclaimed seafood chefs.

Our disappointment upon discovering we are too late for the stew competition ends once we find ourselves sitting by the water, feasting on a plate of freshly shucked oysters served simply with some homemade cocktail sauce and lemon. This bounty of bivalves tops off our afternoon with pure seafood perfection.

With dinner time upon us, we happily leave our parked car once again and mosey across the street to high-end eatery 208 Talbot, where Chef Brian Keegan has put together a menu of locally sourced fish and produce. And what he doesn’t procure at the Eastern Shore’s finest farms, he makes in-house, including cured hams, sausages and smoked meats.

Taking advantage of the regional seafood is the order of the evening, and we begin with Grilled Spanish Octopus with white bean puree and chimichurri and Fried Oysters with preserved lemonalmond pesto, caper mayonnaise and serrano ham. Each oyster I eat seems to get better and better, and this lightly-fried preparation proves a beautiful way to showcase the star of the weekend.

We also pay tribute to the surrounding waterways with our main courses and delight in dishes of Seared Sea Scallops with carrots, parsnips, butternut puree, toasted pecans and a touch of white truffle oil; and Grilled Fennel Stuffed Rainbow Trout with pear, homemade bacon, spinach, raisins, pine nuts and parsley pesto.

Our final few hours in St. Michaels begins with a lovely little continental breakfast at Five Gables and ends with a much anticipated appointment at the inn’s spa.

Our massages are customized with Aveda aromas of our choice (brought to our room pre-treatment for sampling), and massage therapist techniques pamper my muscles with just the right amount of soothing pressure to rejuvenate me for the ride home.

Relaxation, small-town enchantment, fine dining, fresh autumn air and oysters aplenty—our time in St. Michaels was well spent. It’s certainly not hard to fall for this place. Mission accomplished …and more.

Categories: Weekends