860 Washington Ave, Chestertown, MD 21620  •  Call us  (410) 778-9008


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Our customers love us. Read for yourself.

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 Dealerships

“I have very complex and difficult personal insurance needs. I place a premium on ease, simplicity and straight communication. That's why I'm so pleased with  Chesapeake Benefits. They placed everything I was looking for in a prompt and responsive manner.”

Mr Herbert Ford, Farmer Chesapeake Benefits Customer

I just wanted to send a note to thank you for all of the work you have done for The Aspen Institute over the years. You have consistently guided us in a professional way through the complex and seemingly ever changing world of employee benefits. As you know, when we have made decisions to change carriers or make changes to our plans, those decisions are not only based on what we believe the carrier can provide us, but also on the fact that we know you will be an important part of the ongoing relationship. I look forward to our continuing relationship.”

Dolores Gorgone,

Chief Financial Officer

The Aspen Institute

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 Dawson,

Executive Committee Member

Kent Forward


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860 Washington Ave, Chestertown, MD 21620

(410) 778-9008