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Great Products, Fair Price,
Excellent Service

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At Pilot Car Insurance, we offer the peace of mind and reliability you deserve. When you need commercial insurance including automobile, general liability, professional liability, or equipment and tool coverage—trust our experienced team to find the best solution at the best price. You know how to run your business, let us protect it.

Our Team

Peggy Cash, Pilot Car Insurance, Winchester TN

Peggy Cash

Heather Gifford, Pilot Car Insurance, Winchester TN

Heather Gifford

Alejandra Medley, Pilot Car Insurance, Winchester TN

Alejandra Medley

Account Manager, CLCS

Katy Weber, Pilot Car Insurance, Winchester TN

Katy Weber

Contact Us With Questions, Comments, or for a Quote

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“ The company to go to in Winchester for all your insurance needs! Friendly, knowledgeable staff treat you like you are the only customer.”

— Steve S.

“These guys deserve more than 5 stars! The best insurance company out there. Great communication and response time is what they offer.”

— Dylan T.

“Katie is great at what she does. She is quick to answer any questions that I have dealing with my pilot car insurance. I haven’t always made it easy on her, Lol. The website is pretty easy to navigate online. As far as Katie goes she gets a big thumbs up and I look forward to doing business with y’all now and in the future.”

— Jacquelyn R.

“Very satisfied with the amazing service! Extremely helpful staff.”

— Brant B.

“Fast, friendly customer service! Their agents really know their stuff! V. R. Williams goes above and beyond to make sure you are getting the right coverages that you need! Best agent in town!”

— Dusty B.

Pilot Car Insurance | A Division of V. R. Williams & Company


Pilot Car Insurance
1784 Sharp Springs Rd
Winchester, TN 37398
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Pilot Car Insurance
PO Box 458
Winchester, TN 37398

Phone: 931-313-5519
Fax: 931-967-1128


Monday – Friday:
8:00 AM – 5:00 PM
Saturday – Sunday:


V. R. Williams & Company supports, through charitable donations, and is a member of:
SecureRisk Insurance Solutions, partner agency, Winchester TN
Franklin County Chamber of Commerce, member company, Winchester TN
Insurors of Tennessee, partner agency, Winchester TN
Special Forces Charitable Trust, partner, Winchester TN
The purpose of this website is to provide information about V. R. Williams & Company and its affiliated companies. Insurance coverage cannot be bound or changed as a result of submitting a request for information or quotation of insurance via submission of this online website. Completion and/or submission of applications, additional information, or quotations does not constitute the purchase of insurance, nor does it represent any agreement to provide coverage under any insurance policy. Only coverage that has been confirmed by V. R. Williams & Company will be considered bound. Coverage is subject to an acceptable signed application and receipt of proper payment, while meeting underwriting guidelines of the Insurance Company providing the coverage. Any proposals of insurance that may be presented to you through this website will be based upon the values developed and exposures to losses disclosed to us on this online form/application. Information submitted via our website will be held confidential and will be used for insurance purposes only.