Visitors to the Eastern Short of the Chesapeake Bay Will Find

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.

Photographs by: William Wilhelm |

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