LighthouseWhile Native Americans have inhabited the region for thousands of years, the first Colonial owner of the Prospect Bay area was Richard Bennett, Sr., a Puritan governor of Virginia.  Bennett received a land grant on the Eastern Shore of Maryland and moved to what is now Prospect Bay.  At that time tobacco was the main product grown in the area, for export to England.
Little is known about the next generation’s owner, Richard Bennett, Jr., save that he died in 1667 at age 35.  His son, Richard Bennett, III was born in 1667 and inherited the estate at his birth.  It was not a large estate, consisting only of the land, a house, few slaves, three servants, and “tenn cowes and a bull”.  Young Bennett’s mother, Hennrietta Neal Bennett, was the trustee of the property and estate.
Between 1700 and 1749, Richard Bennett, III owned over 30 plantations in the area.  At the time, he was the largest landowner in the State of Maryland.  His heir, Edward Lloyd, Jr., owned over 40,000 acres of land on the Eastern Shore.
During the War of 1812, the British landed on the Eastern Shore, took Queenstown, burned and sacked it.  The Americans then engaged the British and defeated them at the battle of Slippery Hill right at the entrance of Bennett Point Road.  The Americans then fell back to Piney Neck, of which Prospect Bay is a part.

Birth of Prospect Bay Country Club

Fast forward a couple of hundred years……


In 1978 Albert Turner of MCD Enterprises, Inc. (a large Washington, DC builder) and Roy Kilby developed plans for Prospect Bay Plantation West.  Construction of the golf course was commenced.  A boat basin was excavated and that soil was used for fill on the golf course.  The barns and silo were intact and roads were laid out.  Various improvements were made including construction of the original clubhouse, addition of the swimming pool, cart paths along the golf course and house construction began.
The current clubhouse was built in 2005, along with a number of other major improvements to club properties, including a new golf practice facility.  The current clubhouse consists of two dining rooms and grille room with bar, two locker rooms, a meeting room and activities room.  The club is run by a General Manager and staff as well as a 9 member Board of Directors.  The Golf Shop is managed by a golf professional and assistant professional along with a Grounds Superintendent and staff.  The club hosts many weddings and golf outings each year.
Today, Prospect Bay is the site of 320 homes whose many amenities include an 18-hole golf course, clubhouse, tennis courts, swimming pool and marina. The area is the winter home to many Canada Geese as well as many varieties of ducks and waterfowl. 

Some historical notes:
-1986  - Tennis Association formed
-1987 - Yacht club was founded
-1987 – 1997 - Men’s Club was organized
-MISGA – Maryland Interclub Senior Golf Association
-MGA – Men’s Golf Association
-1981 - 18 Hole Ladies Golf Association organized
-1988 - 9 Hole Golf Ladies formed
-1992 - Garden Club formed
-2003 - Paddlers organized
-2005 - Mahjong group formed
-2008 - Polar Bear Swim Team formed
-2010 - Prospect Bay Readers formed
-2012 – Needlecrafters organized

History collected and compiled Linda D. MacIver, 2012