Chesapeake Health Benefits

Eastern Shore Insurance Broker

Trust Worthy

Building trust and fostering lasting relationships are the essence of who we are and a fundamental part of our company values.


Chesapeake health benefits has over 30 years of knowledge in the health insurance industry.


We aim to enhance your ability to recruit and retain quality employees by providing high-value, high-quality benefit programs.

What we Do

Friendly faces with a regional reach

Small Group

Large Group



About Us

At Chesapeake Benefits, No Client is Too Big or Small

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.



Get Started

Don’t Let the Complexities of Health Benefits Burden You Any Longer

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.


“Chesapeake Benefits has been a joy to work with. Our business requires that we have medical, dental and life insurance. Chesapeake Benefits has come through with flying colors on all. The ‘drop everything let me take care of it’ client attitude is what they have given us whenever we have needed anything. Her quick response is matched by none. If you want an agent who makes you feel like you are her only client then I recommend Lori from Chesapeake Benefit Services”

Rachel DeAngelis

Chief Financial Officer, Davis Dealership

“Chesapeake Benefit Services has always worked hard to ensure that our family support agency is properly covered so we can maintain our day-to-day arts activities. Greg Dawson is always just a call away for our small nonprofit. When our coverage needs changed, Chesapeake Benefits did the legwork so that we were properly insured, without missing a beat.”

Linda Sawson

Executive Committee Member, Kent Forward

Join Us

Our Clients Are Like Family

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.

Contact Us

Please feel free to contact us any time. We are prepared to answer questions about our benefits plans, help with claims or simply planning for the future. Whatever the case, we are at your service.

860 Washington Ave. Chestertown, MD 21620

M-F: 8am-5pm, S-S: Closed

7 + 7 =