Dr. Hill is a Talbot County native with four children and two grandchildren.  He is the President and Chief Executive Officer of Caulk Management Company, Inc., a privately held real estate acquisition, development and management company.  Dr. Hill has extensive development and management experience spanning the past fifty years and multiple industries.  Highlights of this experience are provided below.

Dr. Hill is the general partner in Idlewild Associates, a land development partnership which developed an 80-acre site in Easton, Maryland into the major medical community in Talbot County, Maryland.  In this regard, he assisted the doctors who purchased the land in the financing and development of doctor’s offices and other medical facilities.

Dr. Hill is the founder and former Chief Executive Officer of William Hill Manor, which is a retirement/health care community serving the needs of the elderly population though the provision of skilled nursing, convalescent and rehabilitative care with 105 nursing beds, 52 cottages and 63 apartments.  This hallmark facility, located in Easton, Maryland, established an outstanding reputation in its delivery of the highest quality services though a personal commitment to excellence and provides the ultimate in retirement living and health care services.  Under Dr. Hill’s leadership, William Hill Manor achieved financial and strategic success, culminating in its 2004 sale to Episcopal Ministries for the Aging, Inc., a not-for-profit corporation.

Dr. Hill was founder and Chairman of the Board and CEO of Easton Bancorp, Inc., which owned Easton Bank & Trust, of which he was Chairman of the Board and Director. Easton Bank & Trust, was a locally-owned, independent community bank that opened its doors in 1993. In 2015, Easton Bancorp, Inc. was sold to Delmarva Bank Shares, Inc.

Some of Dr. Hill’s other development endeavors include the general partnership of Health Associates Partnership which owned a medical building on Idlewild Avenue.  He has developed and operated a 120-bed skilled nursing center in Cambridge, Maryland. He has designed, built, and operated William Hill Gardens, a 44-bed assisted living facility.  He has also owned or developed a child-care facility and five full-service car washes in two states.  He has been heavily involved in the operations of Hill’s Drug Store, a local full-service pharmacy.

Following the sale of the William Hill Manor in 2004, Dr. Hill acted on his vision to develop a hotel development and management company, Hill Hospitality, dedicated to the pursuit of excellence.  There are currently five hotels under operation.  All of which are performing exceptionally well and are award winning properties. The hotel in Murrells Inlet, South Carolina was ranked number 1 out of over 2,000 Hampton Inns for six straight years. There are immediate plans for at least three additional hotels.

Dr. Hill is the founder of Chesapeake Treatment Services in Easton, Salisbury and Ocean City, MD. CTS is a clinic dedicated to the recovery of individuals struggling with opioid addiction. They offer Suboxone and daily doses of methadone. They provide affordable care in a respectful and welcoming environment for individuals who are suffering with the disease of addiction

Dr. Hill is a long-term supporter of the Talbot County Branch of the American Red Cross donating the land for their facility. He also built and provided the location for the Talbot County Branch of Advanced Life Support along with serving as a Charter Board Member. Dr. Hill has donated time and energy to various other charitable activities and has served on various boards. He was voted Businessman of the Year in 1989 by the Talbot County Chamber of Commerce.