Getaway Guide: Weekend Trip to St. Michaels, MD

August 18, 2012 6:00 AM


Known as the heart and soul of the Chesapeake Bay, St. Michaels is the ultimate weekend getaway destination. Stroll the brick sidewalks, view gorgeous Victorian homes and visit boutique shops located in the heart of town. Don’t forget to enjoy the best seafood Maryland has to offer at one of the many restaurants located along the waterfront on a weekend getaway you won’t soon forget.

Getting There

Head out of the city and toward I-395 north. Take the exit for Pennsylvania Avenue, then continue onto Highway 295. Continue onto MD-201, then take the toll to US-50 east toward Annapolis. Drive for about 16.5 miles until you reach the exit for MD-322 south. Turn right onto MD-33 west, St. Michaels Road. Continue on St. Michaels Road for about nine miles, then turn right onto Carpenter Street. The entire trip should take roughly 80 miles, or about 2 hours, depending on the flow of traffic.

innatperrycabin Getaway Guide: Weekend Trip to St. Michaels, MD


The Inn at Perry Cabin
308 Watkins Lane
St. Michaels, MD 21663
(410) 745-2200

Rates: from $485

Live in the ultimate lap of luxury with a weekend stay at the Inn at Perry Cabin. The gorgeous 19th-century colonial manor includes a lavish spa, heated infinity pool, fitness center and multiple picturesque gardens. Each room offers luxurious amenities, a mixture of modern and period furniture, spacious bathrooms and gorgeous countryside views. Grab a bite to eat at four-star Sherwood’s Landing or grab a drink at Purser’s Pub. Rates include access to the Linden Spa.

stmichaelswinery Getaway Guide: Weekend Trip to St. Michaels, MD


St. Michaels Winery
609 S. Talbot St.
St. Michaels, MD 21663
(410) 745-0808

After a good night’s rest, continue the relaxation mode as you sip a glass of fine wine from St. Michaels Winery. Stop by the tasting room and sample a wide variety of white, red and sweet wines, or sample the staff’s favorite wine selection. No reservations are necessary. Sign up for a tour of the facility, or simply relax on the patio under the shade of a big umbrella.

Related: Getaway Guide to Washington DC

thecrabclaw Getaway Guide: Weekend Trip to St. Michaels, MD


The Crab Claw Restaurant
304 Burns St.
St. Michaels, MD 21663
(410) 745-2900

Known for its steamed Maryland blue crabs, the Crab Claw Restaurant is the ultimate spot to enjoy delicious seafood down by the waterside. Enjoy tasty treats from the raw bar, seafood platters, sandwiches, salads and other light fare. Recognized as the 2010 Best of the Bay by Chesapeake Bay magazine, the Crab Claw Restaurant features a full-service bar plus delicious desserts. Reservations are recommended.

St. Michaels Motor Inn
1228 S. Talbot St.
St. Michaels, MD 21663
(410) 745-3333

Rates: from $135

Enjoy well-appointed and comfortable rooms without breaking the bank. Each room features free in-room wireless Internet, cable television, coffee maker and free local calls. The hotel offers two outdoor swimming pools and is located within a short distance from alluring St. Michaels attractions including the Oxford Bellevue Ferry, Tilghman Island and the Chesapeake Bay Maritime Museum. Enjoy a complimentary full breakfast each day of your stay.

Related: Checklist For A Fun Day At The Beach Or Pool

chesapeakebaymarimuseum Getaway Guide: Weekend Trip to St. Michaels, MD


Chesapeake Bay Maritime Museum
213 N. Talbot St.
St. Michaels, MD, 21663
(410) 745-2916

Grab the kids and head over to the Chesapeake Bay Maritime Museum where the whole family will learn about the vibrant culture, heritage and ecological systems of the Chesapeake Bay. Participate in an overnight lighthouse adventure, or sign up for a guided tour of the museum. Visit the museum library and listen to more than 800 taped oral histories, and view more than 45,000 historical and contemporary photographs. Don’t miss out on a scenic cruise on the Miles River aboard the museum’s own Mister Jim.

Susan Diranian is a freelance writer living in Ashburn, VA. She is covering Travel & Outdoors. Her work can be found at

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