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Club History


While 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 a 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.

Fast Forward a Few Hundred Years…

In 1978 Albert Turner of MCD Enterprises, Inc. and Roy Kilby developed plans for Prospect Bay Plantation West.  Construction of the golf course commenced. The 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. 
Today, Prospect Bay is the site of 320 homes and offers the following amenities to residents and Club Members: 18-hole championship golf course, clubhouse, tennis courts, swimming pool and marina. 

In 2019, the Club embarked on an exciting new capital campaign that will bring improvements and upgrades to the golf course, golf maintenance facility, tennis courts, boat basin and clubhouse. 


Some Historical Notes:

1986  - Tennis Association Formed
1987 - Yacht Club Founded
1987 – 1997 - Men’s Club, Men’s Interclub Senior Golf Association, Men’s Golf Association Organized 
1981 - 18 Hole Ladies Golf Association Founded 
1988 - 9 Hole Golf Ladies Group Formed
1992 - Garden Club Formed
2003 - Paddlers Organized
2008 - Polar Bear Swim Team Formed
2010 - Prospect Bay Readers Formed
2012 – Needlecrafters organized

History collected and compiled Linda D. MacIver