About Us


It’s all about Solutions

Located in historic Chestertown, Maryland, Chesapeake Benefits provides counsel, administrative support, and benefits solutions to employers and employees across the United States. We market quality and affordable group plans to employers, business associations, multi state employers, as well as serving the needs of our local clients.

Friendly faces with a regional reach

Chesapeake Benefits was established in 1987 to administer employee benefit plans to groups in Maryland, Delaware and Washington D.C. Today, the firm has expanded its book of business throughout the entire Mid-Atlantic region, and as far west as Colorado. With the rapid acceleration of benefit costs, the business increased rapidly as employers searched for more affordable benefit solutions for their employees. Over time, Chesapeake Benefits has extended its business into the individual marketplace, offering solutions to those without employer benefits.

Our Philosophy

We believe that quality service to our clients is essential for our success. We maintain the highest level of continuing education, and are devoted to researching new programs and insurance solutions for our customers. We present all viable solutions to our clients, and allow them to decide the best coverage to fit their needs. Our focus shall remain on our clients, and we shall continually strive to find new and better ways to serve them. We shall portray our clients to potential insurers in the best possible light, and devote our efforts to assuring the best possible rate for our clients.

(410) 778-9008

860 Washington Ave

Chestertown, MD 21620

We will call you.

Our Services

Life and A.D & D.
Short Term Disability
Long Term Disability
Long Term Care