Chesapeake Benefits clients range in size from self-employer groups to groups with five hundred lives. In addition, we sell and service many personal plans to local residents. Our staff takes great pride in their abilities to provide insurance solutions and claims services.


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Major medical insurance provides coverage for services rendered through network physicians and facilities. Benefits are subject to network discounts to reduce overall cost for the insured. Plans are subject to deductible and coinsurance, as well as copays, where applicable. The overall cost of the plan is dependent upon the structure of the benefits. Each plan has essential benefits which are required by law to allow for the insured be proactive with their overall health.


Dental insurance allows the insured to receive necessary dental procedures by network physicians. Preventative, basic and major services are covered, by design, to aid in overall cost of dental care. Preventive cleanings are encouraged to promote a healthier lifestyle, as well as examine for future ailments.


Corrective vision benefits provide allowances for lenses, frames, contact lenses, and materials. Vision providers offer discounted services to assist in the cost of corrective vision. Plan cost varies based on the design of the plan and the access of vision providers.

Life Insurance

Life insurance serves as financial security for the policyholder and his/her beneficiaries. Benefits are paid to the beneficiary at time of death to provide financial support at a difficult time. Many benefit riders are available to enhance the quality of the plan. Group life insurance plans are designed to cover employees during their time of employment. Plans can be structured to allow the policyholder to continue coverage should they leave their place of employment. Typically, plans can be issued with a guarantee of coverage, which would not require evidence of insurability. Accidental death and dismemberment (AD&D) riders are commonly included with group life insurance plans to supplement the face value.


Short term and long term disability are insurance policies which provide income to individuals when they are unable to perform their normal occupational tasks. Disability plans are designed to provide a percentage of the weekly or monthly income of the individual, dependent upon the structure of the benefit plan. The duration of coverage can vary based on the design of the plan, as well as the severity of illness or injury. Short term disability is offered for immediate loss of employment due to injury or illness, whereas long term disability covers a longer duration should an individual be disabled. A waiting period exists in some plans to assure that the extent of disability will require time away from employment. The replacement of income is considered by consultants as a vital benefit for employed individuals.

“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 Sawson

Executive Committee Member, Kent Forward

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

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