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About Dairyland

Providing quality coverage at competitive rates for more than 70 years
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Who we are

We were raised with Midwestern roots and built on small-town values—ones we’ve carried with us as we’ve grown from a local vehicle insurer into a nationwide presence.

Our name pays tribute to our history, but our service tells the real story of who we are and where we come from. Because while we may be a business with a bottom line, you’re never just a number.

We promise to always treat you as a person—one who deserves the best service, no matter who you are or what stage you're at in life.

About us

70
Years

Experience you can trust

24/7
Support

Real people to talk to

4.5/5
Stars

Service our customers value

Come as you are

Whether you're driving on two wheels or four, we're along for the ride—providing vehicle insurance to help you keep your car, your bike, and yourself on the right path.

A message from our president

Thanks for visiting dairylandinsurance.com as you're considering insurance providers to protect your car, bike, or off-road vehicle. You’ve come to the right spot for dependable coverage. I’m confident you’ll find that our dedicated staff can assist you with any questions you might have. We’re here to help you find the right coverage, file a claim, or answer your policy questions.

Pete Anhalt
President - Personal Lines

Our history
1916
The first auto insurance policies

The Hardware Dealers Mutual Fire Insurance Company of Wisconsin begins writing auto insurance for its members. Previously, the company sold property and casualty insurance to Wisconsin Retail Hardware Association members. That small business is now known as Sentry Insurance—the parent company of Dairyland.

1953
Dairyland Insurance Company is formed

Stuart Struck, a University of Wisconsin–Madison professor, forms Dairyland Mutual Insurance Company of Wisconsin. The company begins selling specialty insurance for drivers who can’t get standard coverage because of poor driving records, little experience behind the wheel, or no prior insurance.

1966
Sentry and Dairyland

Sentry acquires Dairyland, which at the time wrote non-standard auto policies in 27 states. Sentry also begins to insure riders and their motorcycles.

Customers love Dairyland

Don’t just take our word for it. See what current and former customers have to say about Dairyland insurance.

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Careers

Looking to take the next step in your career? Join the Dairyland team! We offer competitive compensation, a hybrid work model, and strong benefits packages.

View open positions
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Press Room

Stay up to date on the latest Dairyland news, announcements, and initiatives

Visit Press Room

*Dairyland® brand products are underwritten by a member of the Sentry Insurance Group. Sentry has an AM Best Financial Strength Rating (FSR) of A+ (superior), current as of June 2024. See ambest.com/ratings/guide.pdf for rating information.