About Dairyland

Providing quality coverage at competitive rates for more than 70 years
Illustration of motorcyclist riding in front of a Wisconsin farm Illustration of motorcyclist riding in front of a Wisconsin farm

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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


Experience you can trust


Real people to talk to


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.
Pete Anhalt
A message from our president
Pete Anhalt
President - Personal Lines

Thanks for visiting 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.

Our history
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.

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.

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.

Illustration of someone being welcomed to a Dairyland office building.


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.

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Press Room

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*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 2023. See for rating information.