Dairyland: where promises are kept, and people always come first

At Dairyland, we were born in Wisconsin. Raised with Midwestern roots and built on small-town values—ones we’ve carried with us as we’ve grown from a local 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. How? Because while we may be a business with a bottom line, at Dairyland, you’re never just a number. Here, we always treat you as a person—one who deserves the best price and service, no matter who you are.

For more than 60 years, we’ve been offering competitive rates and quality coverage for both auto and motorcycle insurance. So, whether you’re driving on two wheels or four, we’re also along for the ride—helping keep your bike, your car, and you on course.

Our story
  • 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

    Dairyland Insurance Company Logo

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

  • 1975 — More agents recommend Dairyland
    Independent agents join the Dairyland team and begin selling motorcycle insurance policies.
  • 1977 — Sentry builds a new home office
    Sentry Insurance Headquarters
    Sentry Insurance moves into its new (and current) headquarters in Stevens Point, Wisconsin.
  • 1992 — Sentry is rated A+ (superior) by AM Best*
    Sentry achieves an A+ financial strength rating from AM Best, which assures Dairyland policyholders that we will be there when they need us. It’s a ranking that remains to this day. AM Best assigns an A+ (superior) financial strength rating to insurance companies that they believe have a superior ability to meet their ongoing insurance obligations.
  • 2004 — Our centennial

    Sentry Insurance 100 Years logo

    Sentry celebrates 100 years of providing insurance for a variety of businesses and individuals through the Sentry Group of Companies.

  • 2005 — Sentry acquires Viking Insurance®
    The acquisition merges the company with Dairyland, doubling the size of our specialty auto service and expanding our industry expertise.
  • 2016 — A milestone year for Dairyland and Sentry
    Dairyland celebrates insuring riders and their motorcycles for 50 years, while Sentry celebrates writing auto insurance for 100 years.
  • 2018 — A new look, the same quality insurance
    Dairyland unveils its new look and new logo, while providing the same affordable insurance and quality service our customers expect.
Pete Anhalt, Senior Vice President

Pete Anhalt

President – Personal Lines

A message from Pete

Thank you for checking out Dairylandinsurance.com to protect your car or bike. You’ve come to the right spot for either automobile or motorcycle coverage. I’m confident you’ll find that our dedicated staff can assist you with any questions you might have. Just click on the Contact Us tab, and you’ll find phone numbers and a form to send a message to our staff. We’re here to help you find the right coverage, make a claim, or answer your policy questions.
*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 2021. See ambest.com/ratings/guide.pdf for rating information.
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