Ask almost anyone in town where to get a good cup of Joe in St. Michaels, and they will wax poetic about the town’s most happening morning spot, Blue Crab Coffee. Here, tucked behind the Acme on Fremont Street, barristas serve double lattes and decaf cappuccinos in a lovingly restored 1883 landmark, the Freedom’s Friend Lodge, one of the only African-American lodge buildings still standing. “We have a faithful local clientele,” says Aaron Schultz, a barrista at the coffee shop for the past seven years. “A lot of people come here to get the word on the street.”

Walk through the petite town (only one square mile), and you’ll find quiet, narrow streets filled with quaint eighteenth- and nineteenth-century homes, their front porches bedecked with hanging baskets. But with its increasing appearance on national lists of must-visit spots, St. Michaels is on the verge of becoming Maryland’s most upscale destination, its own version of Nantucket. And like that island enclave, here the rich and powerful share downtime with longtime residents in this changing town just an hour from the Bay Bridge. (They’re pretty used to the Vice President dropping in for a bite or doing a little shopping.)

Over at the posh waterfront Inn at Perry Cabin, a Rothschild family checks in for a couple of weeks each summer; Sarah Jessica Parker and her fellow stars slept here when Hollywood came to town last summer for a movie shoot. The well-heeled dock their staffed yachts in the harbor and stride into the comfortably elegant lobby, nannies and lapdogs in tow. “It has almost become commonplace for the locals to encounter the stars and dignitaries that come to town,” says Brian Plaska, The Inn at Perry Cabin’s director of sales. “They’re simply accepted as just another guest of St. Michaels. It’s nothing new to us.”

St. Michael'sAmid the fancy restaurants and upscale women’s boutiques—where ball gowns are not uncommonly spotted—the Eastern Shore’s traditional preppy, outdoorsy flavor is alive and well at spots like the Carpenter Street Saloon and Keepers, purveyor of Orvis gear and clothing. “Our customers are still looking for that classic Eastern Shore feel,” says salesperson Kathleen Harrison, a St. Michaels native. “Sure there are fancier spots around town, but those who are into the outdoorsy, no-frills Eastern Shore lifestyle keep coming to us.”

It’s not surprising that St. Michaels is having an identity crisis. Half the homes are owned by people who come to escape their working life elsewhere, drawn to the picturesque downtown, marinas, and surrounding rural landscapes. Heron and osprey co-exist with 1,200 or so year-round residents on this peninsula between Tilghman Island, Easton, and Oxford. It’s a place devoid of franchises, where fine dining options outnumber sub shops.

St. Michael's“There are a lot of transient people who have moved here, weekenders mainly,” says resident Sue Waite, who moved here with her family in 1992, when St. Michaels was just beginning to make the transition from sleepy burg to ritzy weekend destination. “People have gotten used to it. But it does leave a kind of a disjointed feeling.”

Any local can tell the tale of how the town fooled the British during the War of 1812 by hanging lamps in nearby forests to draw fire away from the harbor. As plucky as the town was back then, today it’s just as proud and likely able to hold its own and sustain its charms against an approaching high tide of developers and homebuyers.

Even non-history buffs can appreciate the stops along St. Mary’s Square Museum walking tour: the Small Frame House (circa 1800), one of the last shipyard workers’ dwellings; the Gothic Revival Union United Methodist Church, built in 1895, which retains the original colored glass windows, bronze chandeliers with milk glass globes, and pipe organ.

St. Michael'sVisitors can bunk at the 1799 Dr. Dodson House or sleep where Gen. Robert E. Lee did, in the Colonel Joseph Kemp House, a Georgian-style residence built in 1807, now an inn.

Maritime history is inescapable here, too. The eighteen acres of the Chesapeake Bay Maritime Museum are perfect for an afternoon stroll or picnic lunch, but many visitors plan their stay around the annual antique boat show (June), the Crab Days festival (July), or OysterFest (November). It still boasts a rich hands-on experience, with the nation’s most complete collection of Bay artifacts and visual arts, and the largest group of indigenous watercraft in existence; an entire new wing highlighting the culture surrounding the boats opened last fall.

Don Conley is a bit of living maritime history. His thirty-six-foot deadrise charter, Let It Ride, trolls the local waters, providing a unique view on what it’s like to live in a place where homes put their best side to the waterfront. Conley dispenses local lore and insider commentary as his two-hour tours drift slowly past multi-million dollar homes, up Miles River, into Leeds Creek, and around the sunset-filled harbor. “A favorite sight is one of the oldest residences,” he notes, “the Pink Castle, built in 1860. Another is the Johnson & Johnson estate, recently purchased by Stewart Bainum of Manor Care. People also get excited if we spot an eagle, which happens on occasion.”

St. Michael'sResidents debate how to handle inevitable growth, but reluctance to change is nothing new. In 1978, when James Michener was writing his novel Chesapeake, he sensed some interview subjects “hoped I would quit my project and go elsewhere, lest my writing awaken the rest of the world as to what a sequestered paradise they were enjoying on the Eastern Shore.”

Today, homeowners are taking sides over a developer’s proposal to build a 280-unit project called Miles Point adjacent to The Inn at Perry Cabin. With construction of that scale and a surge in population, St. Michaels may beat Nantucket in a reluctant race to the first traffic light.
Locals’ Guide to St’ Michaels

Muskrat Love
Fine summer evenings begin at Muskrat Park, which hosts free outdoors concerts every Thursday evening from 6:30- 8 p.m. beginning in June. Grab a lawn chair, and stop by Village Shoppe for a pint of its famed chicken salad and roasted red pepper and corn salad to stuff in your picnic basket. For concert schedule, call 410-745-6073. Village Shoppe, 501 S. Talbot St. 410-745-9300.

Party Girls
Locals know that they can book private, after-hours shopping parties for eight to twelve women at Charisma, a clothing boutique perfect to feed your inner Crystal Carrington with its healthy inventory of sequined items. Perks include 10 percent discount on clothing, complimentary beverages, and appetizers or desserts. 201 S. Talbot St. 410-745-0352.

Caribbean Character
Who needs the islands when you’ve got the patio bar at Character’s Café? Potted palm trees and lush hanging baskets lend a tropical feel, while music from the local bands gives it a funky edge. 200 S. Talbot St. 410-745-6206.

Going to the Dog
If the town’s April food and wine festival is too staid for you, come for the annual Jack Russell Terrier Races, sponsored by local pet boutique Flying Fred’s. (Yes, Fred is a Jack Russell.) The races are held every October on the lawn of The Inn at Perry Cabin (which has a number of pet-friendly rooms, if you want to bring your own pooch.) Flying Fred’s, 202 N. Talbot St. 410-745-9601 or http://www.flyingfreds.com.
When You Go

General Information: http://www.tourtalbot.org or 410-770-8000
STAY

The Inn at Perry Cabin plays host to the rich and famous—and their pets. Prime waterfront location. In-house fine-dining restaurant is Sherwood’s Landing (reservations recommended). 308 Watkins Ln., 410-745-2200 or http://www.perrycabin.com.

St. Michaels Harbour Inn Marina & Spa, located within walking distance of downtown, has forty-six rooms (some waterfront), a marina, and in-house spa. 101 N. Harbor Rd., 410-745-9001 or http://www.harbourinn.com.

George Brooks House (see story on page 61) is a finely restored circa-1900 Gothic Revival Victorian, located just outside of town, with six guestrooms and a pool. 24500 Rolles Range Rd., 410-745-0999 or http://www.georgebrookshouse.com.
EAT

Blue Crab Coffee, the only coffee shop in town, has a good selection of blends, home-baked sweets, and serves breakfast and lunch. 102 Fremont St., 410-745-4155 or http://www.bluecrabcoffee.com.

Around since 1965, The Crab Claw Restaurant is an Eastern Shore tradition. Outside and indoor waterfront seating available. 304 Mill St. at Navy Point, 410-745-2900 or http://www.thecrabclaw.com.

“C Street” to the locals, Carpenter Street Saloon counts among its regulars everyone from watermen to Rumsfeld. Pool tables upstairs; live music on weekends. Traditional bar fare. 113 S. Talbot St., 410-745-5111.

Gourmet by the Bay offers well-prepared foods good for quick dinners and picnics. A wide selection of wines and cheeses, too. 415 S. Talbot St., 410-745-6260 or http://www.gourmetbythebay.net.

Shore Restaurant & Lounge’s innovative menu includes quail, scallops, lamb, and caviar. Located within St. Michaels Harbour Inn Marina & Spa. 101 N. Harbor Rd., 410-924-4769 or http://www.shorerestaurant.net.
SHOP

One of the country’s top craft galleries, Mind’s Eye Craft Collection represents the work of more than 200 artists working in ceramics, fiber, wood, metal, and glass. 205 S. Talbot St., 410-745-2023.

Keepers carries Orvis gear for both men and women. It also features acclaimed antique and newly hand-carved decoys. 300 S. Talbot St., 410-745-6388.

Chesapeake Trading Co. boasts men’s and women’s apparel from Isda, Lacoste, and Brighton, to name a few. You’ll also find home accessories, books, and CDs. 102 S. Talbot St. 410-745-9797 or http://www.chesapeaketradingco.com

Coco & Company has hip and fun clothing, French bath products, hand-crafted jewelry and home furnishings. 209 S. Talbot St., 410- 745-3400 or http://www.cocoandcompany.com.

Simpatico offers a unique collection of Italian pottery, flatware, and other imported goodies like Cipriani pasta sauces from Venice. 104 Railroad Ave., 410-745-0345 or http://www.simpaticostmichaels.com.