St. Michaels: The New Martha's Vineyard?

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African Americans have had a tradition of summering in coastal resort towns since the 19th century. Areas such as Martha's Vineyard, Mass., and Sag Harbor, N.Y., have been attracting black families for more than a century. The primary reason blacks flocked to certain areas was that they were barred from or made unwelcome in other places.


In our modern, "postracial" times, many blacks have the freedom, money or clout to vacation wherever they choose. Like their white counterparts, affluent black families have acquired second homes that are used for more than a summer respite.

One town creating buzz among East Coast buppies and black boomers today is St. Michaels, Md. Historically a waterman and shipbuilding town, St. Michaels has evolved into an elegant yet quaint getaway for the Washington, D.C., power elite. Former Vice President Dick Cheney and former Secretary of Defense Donald Rumsfeld have homes there, and the late Michael Jackson reportedly looked at property in St. Michaels before his death.

Only 90 minutes outside of Washington, the exclusive waterside community is an ideal alternative to traveling a longer distance to popular northern destinations. Proximity, however, is not the only quality that is attracting the attention of black Washingtonians. "Some of the best antiquing around" and "that old-town feel" are what attracted Timothy Hill to purchase a time-share in St. Michaels.

It possesses a kind of dressed-down ease while maintaining a sense of luxury that today's movers and shakers crave when escaping the pressures of urban life. "Everyone wants to live the dream," says Laton Palmer, a financial executive and longtime visitor to St. Michaels.

"Hip and historic" is how Marianne Yost, owner of Rupert's London Bar and Tea Room, describes St. Michaels. Her description couldn't be more accurate. Mixed in with historic Victorian and Federal homes are fabulous new waterfront estates straight out of Architectural Digest. Alongside 19th-century inns are boutique bed-and-breakfasts and luxury resorts complete with state-of-the-art spas. Talbot Street, the main drag, is a mixture of fashionable boutiques, antique shops and stylish cafés amid old-world architecture. 

I fell in love with the long, tree-lined driveways, the fresh seafood and most of all the friendliness of the residents and shop owners. St. Michaels was everything that I love about the intimacy of a small town, with all the accoutrements of fine modern living. 


My travel companion (my big sister), Ericka, and I set out on our beach cruisers to fully explore St. Michaels after a breakfast of fresh croissants and homemade preserves on our patio overlooking the Chesapeake Bay. With the sun on our faces and the wind blowing through our hair, we left no stone unturned. Although, as I told my sister, I "wanted to eat the whole town with a spoon," the following attractions were my absolute faves!

The Inn at Perry Cabin: Any big-city "hustle and bustle" that I felt quickly melted away upon our arrival here. The property itself, set right on the bay, is an impressive show of stately "country home" perfection. I was greeted by the smell of freshly cut grass, butterflies, fresh lemonade and smiles.


Then I was handed an engraved brass key (yes, a real key). My suite was nautical elegance and luxury at its best. Our dinner at the inn's restaurant, Sherwood Landing, was exceptional. The bread could have been a pleasurable meal all by itself. Made by local resident and master baker Gussie Harmon, it tasted like a combination of angel kisses and sunshine. 

Executive Chef Greg Brandburg prepared a flawless culinary parade of regional favorites punctuated with modern gourmet delights. The lobster melted in my mouth. The creamy gazpacho with cucumber sorbet caused me to discover taste buds I never knew I had.


Aside from the beautiful Linden Spa, the grounds and the fantastic cuisine, my favorite thing about the Inn at Perry Cabin was the service. The entire staff goes above and beyond to make you feel comfortable and pampered. This little piece of heaven on the bay delightfully exceeded all of my expectations.   

Take Me Home: Intrigued by the name, I entered this boutique and immediately started oohing and aahing over all of the fabulous merchandise. Owner Regina Namlick has assembled an impressive collection of everything darling. There was everything from sassy stationery, handmade candles and linens to delicate jewelry and treats for your pets. The store itself is "shabby chic" at its best. I wanted to live there!


Rupert's London Bar and Tea Room: When I informed my friend, St. Michaels resident and telecom executive James Woodyard, that I was going to visit his town, one of the first things he said was, "You've got to go to Rupert's and ask for Marianne." After I received this same advice from three other residents, there was no question about where we'd be dining.

"Sophisticated comfort" is how I would describe the decor. My favorite touch was the framed vintage Interview magazine covers on the wall featuring '80s pop icons. Brimming with good cheer, owner Yost gave us a warm greeting and an invitation to sit at the community table — which, by the way, is where it's at! We dined, had lively conversation and laughed for hours with Yost and other colorful locals. It's the perfect modern saloon. Great food and fantastic cocktails.


The Willow Grande: Perhaps the most fashion-forward boutique on Talbot Street, it sports a very hip ready-to-wear inventory. The second level is a bridal boutique with elegant and unique selections for the modern bride. I could think of worse places to have your wedding. 

208 Talbot: If you're a burger lover, you'll love this casual little dining spot! The burgers are perfection. Try the "Mighty MACKenzie."


Frederick Douglass Park: Although it's not much more than a plaque and a park bench, I love this spot because it pays tribute to the important connection that St. Michaels has to American history. It's in St. Michaels that Frederick Douglass made the important decision to escape in search of his freedom. Gotta love that!

Kristi Riggs is a Washington, D.C., fashionista and freelance writer. Follow her on Twitter.