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Getaway Guide: St. Michaels, MD

September 21, 2012 7:00 AM

(Credit: Jay Lloyd)

Reporting Jay Lloyd

If a town can be described as lazy and robust at the same time, it’s St. Michaels, Maryland. Tucked on the eastern shore of the Chesapeake Bay and arranged around a bustling, protected harbor, St. Michaels offers laid back days spent exploring the history and scenic beauty of the Miles River and Chesapeake region and nights of cracking crabs or mingling and tippling at waterfront and Talbot Street bars. The centerpiece of this historic village–that once took a cannonball hit during the War of 1812–is the Chesapeake Bay Maritime Museum, with its unique “screwpile” lighthouse that was transplanted from bay waters to a new home on museum grounds. The museum is surrounded by marinas, B&B’s, rental cottages, a full scale resort, restaurants and unusual shops with nautical flair. Here’s where to go, stay and find that bounty of the bay crabs–steamed, spiced and ready for pickin’. – Jay Lloyd


Two Swan Inn
203 Carpenter Street
St. Michaels, MD 21663

The Two Swan Inn is ideally located on the waterfront adjacent to the Maritime Museum, and just few blocks from the center of nightlife and more than a half-dozen top restaurants. It’s an 18th century inn that has all the charm of a bygone era when life revolved around the bay, its commerce and fishery. Period furnishings provide an aura of authenticity for an overnight stay in a historic environment. Four adjacent cottages serve as guest quarters for visitors who want more than a room. If you come by boat, the inn is part of the Higgins Yacht Yard, and overnight docking is available at the doorstep.

Best Western
1228 S. Talbot Street
St. Michaels, MD 21663

For more traditional digs, the Best Western offers basic rooms at a reasonable price. I find it a convenient stop for overnight stays while attending weddings and races at the nearby Miles River Yacht Club. Rooms are average motel size and clean, and the service is good. Continental breakfast is included, but the town offers some great breakfast spots that are worth adding a few bucks to the getaway budget.

crab20claw1 Getaway Guide: St. Michaels, MD

(Credit: Jay Lloyd)


These three spots offer those famous Chesapeake steamed crabs.

The Crab Claw

304 Burns Street
St. Michaels, MD 21663

Whether you’re inside or on the waterfront deck, there’s a great view of the harbor and the museum lighthouse. The crabs are fresh from the bay and superbly steamed. Chase it with a pitcher of beer, and you can crack and sip the afternoon away.

St. Michaels Crab and Steak House
305 Mulberry Street
St. Michaels, MD 21663

Set right on the water near the St. Michaels Marina and offering both indoor and outdoor seating, this eatery is a fall favorite with Chesapeake boaters. For the occasional visitor who doesn’t want to grab a crab, the menu is varied and includes steaks ranging from a 14-ounce strip to a 16-ounce ribeye.

Chesapeake Landing Restaurant
23713 St. Michaels Rd.
St. Michaels, MD 21663

Off the water, the crab prices are dramatically lower. This year-round eatery just outside of town specializes in steamed crabs and fresh oysters. The large welcoming dining room is backed by a retail seafood shop that provided heavy September crabs for one of my recent dockside picnics. If the weather is right, do the take-out. Be sure to have a knife, mallet and plenty of paper towels, though!

lighthouse1 Getaway Guide: St. Michaels, MD

(Credit: Jay Lloyd)


Pay a visit to the Maritime Museumand explore the lighthouse, from its living quarters to the powerful lens that guided shipping on the busy bay. See the collection of restored historic boats that provided livelihoods and recreation on this vast waterway.

Take a cruise on the “Patriot,” a replica bay ferry that carries visitors on a scenic tour of the Miles River and around the St. Michaels waterfront for a view of historic homes and the thriving maritime industry. The Patriot sails from the Maritime Museum. Or, see the sights under sail on an eye-filling vintage catboat, the “Selina II.” The two-hour cruise accompanied by the sounds of wind and water is a unique way of experiencing Chesapeake sailing heritage.


From Philadelphia, take I-95 South to 896 towards Middletown (last exit in Delaware). Follow 896 to Route 301 South to Route 213 South. Follow 213 to Route 50, turn left onto 50 East. Upon approaching Easton, bear right onto the Easton Bypass (Route 322). Follow Route 322 through three traffic lights. At the fourth light, bear right onto Route 33 (St. Michaels Road). Follow that road for nine miles to the town of St. Michaels.

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