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Hidden Gem on the Chesapeake Bay

Author: Karen Jones | Published: Tuesday March 29, 2011

Read the article on Long Island Pulse Magazine

Though the Chesapeake Bay area of Maryland is home to all variety of quaint coastal villages, St. Michaels is a true find. Tiny and loaded with charm, it boasts a rich maritime heritage, eclectic boutiques, historic inns, antique shops, art galleries, spas and all manner of eateries. There is even a local brewery and winery. However, it is the magnificent harbor-front locale of the surrounding Miles River that will captivate you. Whether you are sailing, yachting, kayaking, fishing or planted on terra firma and feasting on plenty of fresh blue claw crab, historic St. Michaels is a seaside delight.

Located on the eastern shores of the Chesapeake about 10 miles from Easton, Maryland, St. Michaels (about 4hrs south of Manhattan by car) is known as “The town that fooled the British.” It is said that late one night during the War of 1812, residents placed lit lanterns high up in the trees and on ship masts so the cannons of the invading Brits ended up overshooting the town. That inventive spirit survives today.

St. Michaels’ proud maritime history includes shipbuilding, oystering and crabbing, all of which are beautifully represented at the Chesapeake Bay Maritime Museum ( Featuring 15 buildings full of interactive exhibits spread across 18 pristine waterfront acres, the museum celebrates the area’s rich history and culture—and don’t miss exploring the 1879 Hooper Strait Lighthouse. The museum will also host the Chesapeake Folk Festival July 23rd, 2011.

Talbot Street is the main drag through St. Michaels and features dozens of beautiful Victorian and Colonial storefronts. You will not find a Starbucks here but you can visit Ava’s Pizzeria for her wood-fired gourmet pizzas; Big Al’s Market & Seafood for steamed crabs (eat in/take out); Rupert’s London Bar & Tea Rooms for its famous crab soup; 208 Talbot Restaurant & Wine Bar for New American cuisine (try their new 208 Burger for a more casual vibe) or the Carpenter Street Saloon for the “coldest draft in town.”

If you plan to travel in April, the shops along Talbot Street throw open their doors for the annual St. Michaels “WineFest” celebration featuring local vintages, gourmet goodies and more. This year’s festive fun runs from April 29th through May 1st.

For your traditional crab feast, make haste to the harbor where waterfront dining is de rigueur during the warm weather. Bob Pascal’s St. Michaels Harbour Inn, Marina & Spa offers dynamic indoor/outdoor views. If you don’t care for crab, do not let on; just order the chef’s English fish & chips—a massive portion fried to perfection. Other harbor favorites include the Crab Claw Restaurant, Crab & Steak House and Town Dock Restaurant. Come hungry and don’t spare the Old Bay seasoning.

For shoppers, there are all sorts of specialty boutiques with names as quirky as their inventories, like A Wish Called Wanda, Fine Old Posters and Flying Fred’s Gifts for Pets. Antiquing and art enthusiasts also have a number of galleries and shops to choose from.

There is no shortage of accommodations in St. Michaels. The Inn at Perry Cabin ( is consistently rated as a top luxury hotel, which it shows in everything from staff to services. Designed in the Colonial style and loaded with amenities, it expertly blends modern and period décor with classic nautical motifs. Also on the grounds is the award-winning Linden Spa.

The Five Gables Inn and Spa ( is located right in town and is steeped in charm while the aforementioned Bob Pascal’s St. Michaels Harbour Inn, Marina & Spa ( is a full-service resort with 46 waterfront suites and 52 slips at its marina. Golfing enthusiasts might want to stay just north of town at the spacious Harbourtowne Golf Resort (, which features an 18-hole Pete Dye designed course.

St. Michaels is well known as a yachting destination—you’ll see sailing vessels of every shape and size fill the harbor and the Miles River. If you are a true boating enthusiast, time your visit for the Antique & Classic Boat Festival, June 17th-19th 2011, at the Chesapeake Bay Maritime Museum—it’s the largest in the Mid-Atlantic region. Meanwhile jet skis, kayaks, sail boats, power boats and tip-to-toe fishing gear are all available for rental. If you prefer to kick back and let someone else be the captain, there are sailing tours, paddle boat tours or you might take a cruise aboard the Patriot—a St. Michaels institution for over 40 years.

No matter what you plan for your St. Michaels visit, it will be easy to kick back and relax. For more information visit the Talbot County Tourist Board,

Southern Living Magazine ranks St. Michaels in the top 3 “Best Small Town Getaways”!

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake BayChesapeake Bay Magazine’s readers and web community have cast their votes in their annual “Best of the Bay Survey”, and St. Michaels was for The Best Town for Families, Best Town for Foodies, Best Town for Nightlife, Best Town for Sightseeing and The Best Town For Inexpensive Docking!

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Laps of Luxury

Can’t afford that multimillion-dollar Talbot County dream house? At these nine palatial estates, you can live the good life for a week at a time.

Written By Kessler Burnett & Joe Sugarman

  1.  Blowing In The Wind

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay, Prarie Wind
If your tastes tend toward contemporary, there are few more stunning homes on the Bay than Prairie Wind, located just outside of St. Michaels. Designed by Washington architect Suman Sorg and Associates and landscaped by fellow D.C.’er James van Sweden, Prairie Wind looks like a home straight out of last’s month’s Architectural Digest. Three attached wooden buildings house a central living area with funky modern furnishings—chairs and loveseats come in vibrant reds, yellows, and oranges. Views out of the two-story, floor-to-ceiling windows are of tall reed grass and sunsets over the Bay. (Heck, even the view from the bathtub is stunning.) The adjacent buildings house two master bedrooms and full baths. If you can ever tear yourself away, a circular swimming pool surrounded by more reed grass awaits outside, as do several footpaths leading down to a private Bay-side beach.—J.S.

Price tag: $5,000 per week

Book it: 410-745-5255

2.  Green Acres

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay, Millwood Manor.
Ah, the pleasures of estate life: just you, the wildlife, and a host of groundsmen, all of whom are charged with maintaining Millwood Manor’s 100 acres. Take a jog along the miles of mowed paths, most of which border the Tred Avon River or stop and smell the roses blooming in the six-acre garden. The three-bedroom, circa-1800 property—complete with a two-bedroom guest cottage, tennis court, and resident pheasants—was occupied by Owen Wilson while filming Wedding Crashers. But it’s anything but high-profile thanks to its mile-and-a-half, tree-lined driveway that keeps the estate wonderfully hidden from the rest of the world.—K.B.

Price tag: $8,000-$10,000 per week

Book it: 410-745-5255

4.  Sweet Dreams

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay, Sycamore Llanding.
Chandeliers, chaises, and 600-thread-count cotton sheets. What more can you ask for in a master bedroom—except, of course, a fireplace, four-poster king-size bed, and plush carpet? Sycamore Landing has these spoiling details—and more. Modern-day princesses (and princes) will also appreciate the suite’s walk-in closet, and great view of the Miles River. The circa-1659, five-bedroom property is one of the oldest estates in the county and is a favorite haunt among Washington, D.C., politicos, who likely prefer the library, complete with grand piano and deep leather sofas. Brandy and cigars before retiring, anyone?—K.B.

Price tag: $5,000-$7,000 per week

Book it: 410-745-5255

6.Thomas Jefferson (Would’ve) Slept Here

If you’ve ever wanted to stay the night at Thomas Jefferson’s Monticello—but the guards kicked you out at closing time—then book San Sano, located between Easton and St. Michaels. The regal, multicolumned entryway clearly shows T.J.’s influence, and pulling up along the white gravel lane lined with London plane trees and loblolly pines gives guests a reception worthy of a president. (Or someone with pockets just as deep.) The cream and beige five-bedroom interior is decidedly more modern and accented with stone—the enormous dining room marble fireplace looks as if it could burn a sequoia. Spend your days exploring the 146-acre grounds, five of which accommodate a vineyard, which supplies grapes to Little Ashby Winery nearby. The estate’s name is a nod to a small Italian town, and if you try hard enough while sipping Campari and soda by the home’s enormous swimming pool, you just might convince yourself that those Bay breezes are really


Price tag: $8,000 per week

Book it: 410-745-5255

7.Docking Station

St. Michaels Maryland waterfront vacation home rentals on the Chesapeake Bay | Kirkland Manor
You can pull your Bay cruiser right up to the deep-water dock at Kirkland Hall Manor, a sprawling 1920s, white-pillared Georgian estate, located outside of St. Michaels. Unload your baggage at the private boat house and then stroll across the broad lawn (pass by the swimming pool) to the estate, where the nautical décor theme continues. Inside, there are six bedrooms—five of which have their own private baths and sitting rooms—and a dining room table long enough to accommodate nearly everyone on board. If the weather is iffy, relax with a hardback in the library, tickle the ivories on the baby grand piano, or retire to the game room for a gentlemanly poker match.—J.S.

Price tag: $12,000 per week

Book it: 410-745-5255


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A unique destination in Talbot County, Maryland. Since people have been living, working, and visiting here for about 340 years, we probably can’t claim this is a “recent find.” What we can claim with great certainty is that Talbot County offers the “cure for the common vacation.”

We have heard it said by some that Talbot County is the new Hamptons. ENTREE disagrees with that notion. We don’t think that it is the “new” anything, nor does it need to be. Besides, the Hamptons are so last century. The Chesapeake, the eastern shore and Talbot County have their own distinct identities which, while similar to the Hamptons in some ways, are vastly different in most others. For example, we don’t feel deprived at all by missing out on crowded, overpriced restaurants, negotiating hours of congested traffic or locals who would just as soon see you gone.

Our first trip to Talbot County was in winter and it was exceptional. We were hooked from day one. There were fewer outdoor activities but there was a little snow on the boats and the harbors and the beauty of the countryside was magical. Recently, we returned in the summer and found a completely different experience. This is without doubt a destination for all seasons.

Getting to Talbot County is relatively simple. It is close to several major east coast cities. Washington, D.C., for example, is only a one and a half hour drive. The area is steeped in the history of the United States. Reading that history, it seems that most of what we went through as a nation, from the pilgrims to several wars, to slavery, abolition and building the country, happened in and around Talbot County. A great read, especially if you plan a trip to the area, is James Michener’s novel, CHESAPEAKE.

Today, it is all about recreation, creature comforts and spectacular places to live. Not surprisingly many activities are on the water but a good many are on land-biking, hunting, golf. You can forget about not having enough to do. It seemed to us that every week there was another festival or production, whether music, art or theater. That, of course, is what we referred to as the cure for the common vacation.

There are four principal towns in Talbot County: Easton, St. Michaels, Oxford, and Wightman. They are close together and each is a blend of the old and the new but each are unique in their own way. Three-hundred-year-old Easton centers the county. Easton is the seat of county government and is the more urbanized of the four cities. It boasts the best shopping, nightlife, museums and cultural centers.

Foodies rejoice about the incredible number of great restaurants. There are twelve restaurants in Talbot County in the 2011 edition of the Zagat Guide and that includes Washington D.C. and Baltimore. The Bartlett Pear Inn, described as an upscale American bistro, was one of our favorites. This treasure would hold its own in any of the serious food cities of the country. It has received accolades in Zagat and other publications and is richly deserving of them all. Lunching at The Tidewater Inn is a must. Walk down the street to check out what is on the bill at the Avalon Theater.

The city of Oxford just south of Easton on the Tred Avon River tends to be more historical. It dates back to 1683 and is still one of the best places to live. Naturally, it has a great restaurant: the Robert Morris Inn.

Robert Morris, for those of us who slept through American history, was one of the signers of the Declaration of Independence. The new owners are renowned Chef Mark Salter and his partner Ian Fleming (no, not that one), both of whom recently distin guished themselves at The Inn at Perry Cabin. The Tred Avon Dining Room is in the original 1710 public rooms and offers Chef Mark’s signature dishes plus a wonderful wine list.

St. Michaels may be the best known of the four. It is famous as a historic maritime center as well as a commercial hub with dozens of cute little shops, bistros and galleries. The Maritime Museum, both a museum and a classic boat repair yard, is one of the highlights of the entire area.

The history of the Chesapeake is, to a large degree, the history of ships and sailing. That history lives at the Maritime Museum. Another highlight of St. Michaels, of course, is the spectacular Inn at Perry Cabin for food, lodging and waterfront beauty. If the weather is warm, we would sit outside for lunch at St. Michaels Crab and Steak House. Not only is the seafood tops but you can quiz owner Eric Rosen on anything to do with sports teams in Philadelphia.

Tilghman Island is a water lover’s paradise. It is home to the legendary fleet of lightning fast working sailboats called the “skipjacks.” It is also where most of the “watermen” lived.All the towns of Talbot County are unique but Tilghman is the most original. The Tilghman Island Inn is a fine choice for a great meal and lodging right on the water.

Accommodations in Talbot County are many and varied, including inns, bed & breakfasts, guesthouses, full service resorts, hotels, cottages, and rental homes.

If you are not ready to build or buy then you want to contact Angela Spence at Tidewater Vacations to see what living the good life on the Chesapeake is really like. Angela has taken vacation rental houses to another level. Her properties, on the eastern shore, are some of the finest estate homes in Talbot County and run from two to six bedrooms. Every imaginable amenity is usually included—even a boat if you would like one brought to your private dock. This is an experience to share with your family and/or friends that will be unforget- table. Check out her website at or call (410) 745-5255.

As we mentioned earlier, there is no shortage of activities in Talbot. It is a good bet that you will run out of time before you run out of things to do. One adventure not to miss is a sail with Captain Jeff Mathias aboard the Lady Patty, which is docked on Tilghman Island. Shopping in the area deserves much more coverage, but at least check out The Troika Gallery and Gatsby’s in Easton.

Talbot County has an office of tourism which is always a great help. and (410) 770-8000.

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