Consider Maryland's Eastern Shore If You Want To Sail Into Retirement

Individuals who plan to relocate to a small town for their retirement years certainly have a wide selection of choices in Maryland. In fact, there has been a growing number of quality age-restricted retirement communities for active adults in almost every section of the state. However, for anyone whose idea of the perfect retirement demands a sense of adventure and discovery, no area may be as suitable as the shores of Maryland's Chesapeake Bay.

  Nestled in among the far-reaching Eastern shoreline of this vast waterway, with its numerous tributaries and inlets are a score of quaint village seaports that offer a sense of history and a challenging invitation to the experienced sailor. Here are ports of call that have been home to generations of sailors and fishermen dating back to the 17th century. Places with names like Chestertown, Queenstown, St. Michaels, Oxford and Easton continue to attract those looking for quiet charm, fresh air, summer breezes, and clean water. Boaters, summer residents and weekend visitors are now being joined by retirees seeking to escape the hustle and bustle of city life and longing for a place enjoy the tranquility of the water, whether it be on the soaring waves of the Bay or a quiet inlet for a morning of fishing.

The beauty of the Eastern Shore and its waterways, the opportunity for boating and recreation, the tranquility of a rural setting, and the ambiance of living history set this area apart from the rest of the country. For those who are looking for an alternative to the traffic, pollution and congestion of city life, and a place to retire in the security and relaxed pace of a lovely small town, these small towns afford a rare opportunity for a unique living experience.

Perhaps the most notable of these is Easton, a thriving community of 11,000 that is an arts and cultural center that offers the best of both worlds...the quiet charm of a beautiful small town with ready access to larger metropolitan areas like Washington and Baltimore. With a strong medical community, an eclectic group of art galleries and interesting shops, as well as numerous choices for casual and gourmet, this is clearly a place for retirees who relish the thought of new discoveries and enjoy an enthusiastic approach to life.

In a similar vein, the nearby historic villages of Oxford and St. Michaels, while much smaller are notable for their renovated Colonial and Victorian buildings and warmth and hospitality of their residents. St. Michaels, often referred to as the “heart and soul” of the Chesapeake Bay remains a quaint waterfront village where one can spend the weekend relaxing on a skipjack, eating freshly-caught crabs and oysters or visiting specialty shops and the famous Chesapeake Bay Maritime Museum. And while Oxford today is still a waterman's town, it is enjoying a new resurgence based on tourism and leisure activities.

Located on the banks of the Chester River, at the northern end of the Bay, the historic town of Chestertown dates its founding back to the 1640's. Traditionally known for its shipbuilding past, it proudly displays many restored 18th century homes, lovely churches and interesting shops.

Just across the Bay, on its western shores, for those who might prefer the urban surroundings of a larger city and yet still satisfy the urge to be on the water, one might look at Annapolis, the state capital, as a retirement option. Recognized as "America's Sailing Capital" and home the home of the United States Naval Academy, Annapolis also is a favorite port of call for ocean going yachts. Priding itself on providing a perfect balance of small town charm and big world sophistication, Annapolis, in many ways, retains the atmosphere of an 18th century seaport town with a treasure trove of historic attraction and an abundance of Colonial-era buildings.


Annapolis photos courtesy Annapolis Conference & Visitors Bureau.

This Month’s Spotlight City: Easton