About Us

Our History

Crawford Corporation was established in 1919 by Carroll Crawford, originally under the name Westminster Realty and Insurance. In 1952, Loring Yingling took the reins of the company, creating a major presence throughout Carroll County, Maryland and surrounding areas. In 1969, Crawford Cash was established. Loring’s son, John Yingling, joined the company in 1976 and was named the president of the company in 1983. At that time, the name was changed to Crawford Insurance. John still runs the day-to-day operations with the help of his son, Benjamin Yingling. In 2012, the agency name changed to Crawford Yingling Insurance to support continued agency growth.

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Why Choose Us?

Crawford Yingling Insurance is an independent insurance agency located in Carroll County, Maryland. We take pride in our expertise and professional development. Currently, all of our representatives either hold or are working towards an accredited insurance designation. We specialize in marketing and placing commercial and personal insurance in Maryland, Virginia, and Pennsylvania. Our goal is to educate our clients and advocate on their behalf.

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    Honesty & Respect

    Care for all persons as our own & treat every person with honesty, fairness and respect.

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    Lasting Relationships

    Establish a long lasting relationship based on mutual trust and superior service.

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    Personal Attention

    Provide a risk adviser who knows each client & prides themselves on helping solve clients’ problems.

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What clients say

Crawford Yingling Insurance is a family owned and operated business that has flourished since 1919. Our success rests squarely on our commitment to unparalleled personal service, competitive pricing, and honest business practices.

Being a new business owner, I was completely in the dark on how to get insured and what to expect. Ben came to my shop before I opened and walked me through the process so I could make an educated choice and feel confident in my decision.

-Dawn Pritchard

John and Ben have done a great job of helping me with my business and family insurance, and Jennifer is very efficient and helpful.

-Randy Seeley

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Crawford Yingling Insurance

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John B. Yingling, A.A.I.

President, CFO


After graduating from Towson University in 1971 and working in the financial services industry, John joined Crawford-Cash Inc. in 1976. In 1983, he became president of Crawford Yingling Insurance. In 1995, he earned the Accredited Advisory of Insurance designation (A.A.I.). John is past president of the Carroll County Association of Independent Insurance Agents, serving on the board of the Independent Insurance Agents of Maryland, Inc. He is currently the treasurer of the Greater Westminster Development Corporation, serves on the Board of Carroll Hospital Center and is a board member of The Carroll Community College Foundation. John specializes in business, automobile and homeowners accounts.

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Benjamin Yingling, CIC, CRM, CLCS, CRIS

Vice President


Benjamin serves as Vice President of the agency and oversees all aspects of the business. Ben strives to help businesses implement and leverage risk management strategies to better position themselves in the insurance marketplace. He recently obtained the Certified Insurance Counselor Designation and Certified Risk Manager Designation after completing over 200 hours of coursework and multiple comprehensive essay examinations. In addition, he holds the Commercial Lines Coverage Specialist Designation, Construction Risk Insurance Specialist Designation. Ben sits on the Board of the Maryland Chamber of Commerce, is former Chairman of the Board for the Carroll County Chamber of Commerce, He is a board governor for the Loyola Blakefield Alumni Association and is past chairman of the Carroll Hospital Golf Committee. Ben is also an active Rotarian and sits on the Westminster Boys and Girls Club Capital Campaign Committee, He resides in Westminster, MD with his wife, Amy.

Fun Facts:

  1. Has jumped off The Las Vegas Stratosphere TWICE!!
  2. Loves to cook
  3. Is absolutely terrified of Bees
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Jennifer Trimble, ACSR

Account Executive


Jennifer joined Crawford Yingling Insurance in 2013 after serving multiple roles in the mortgage industry. Jennifer specializes in servicing business and personal lines accounts. In 2015, Jennifer obtained the Accredited Customers Service Representative Designation, a highly respected and sought-after accolade in the industry. Jennifer’s effective communication and expertise has garnered her high praise from clients and her peers. Jennifer holds an Associates Degree in Business Management from Frederick Community College and resides in Frederick, MD with her husband, Mark.

Fun Facts:

  1. My favorite snack is chips with salsa
  2. I love reading books
  3. I rode horses in middle and high school

Rayna Wise



Rayna joined Crawford Yingling Insurance in 2018. She has worked in customer service since 2015 and is currently pursuing a Bachelor’s in English and a teaching degree at McDaniel College.

Fun Facts:

  1. My favorite animals are alpacas.
  2. I sing and play various instruments.
  3. I am studying to be a middle/high school English teacher.

Excited to work with us? We are ready to start