Why Dairyland?

We know it might seem odd that you would purchase your insurance through a company named "Dairyland." We sell insurance nationwide, but we're based in Wisconsin. It was either Dairyland or Cheesehead. There are no holes in our coverages, so quite frankly, Dairyland just felt right.

You'll appreciate our warm and helpful staff, regardless if you call our Wisconsin customer service center, or one of the many scattered across the country. Dairyland customers routinely rank our staff excellent for being helpful, friendly and reliable.

Dairyland Auto® provides competitive rates, money-saving discounts and outstanding customer service. You will receive low down payments and monthly payment plans, so you can "pay as you go." With Dairyland Auto®, all types of drivers can receive immediate insurance coverage. Learn more about auto coverage options, discounts or start a quote on our Auto pages.

We've been insuring riders since 1966. Dairyland Cycle® offers competitive rates, money-saving discounts and exceptional customer service. In fact, many of us are riders too. You can rest-assured that if you are involved in an accident, we will work hard to get your bike back to the condition you had it, and we won’t skimp on parts or paint. We're not too particular about what kind of bike you own. We even insure scooters and mopeds. Learn more about cycle coverage options, discounts or start a quote on our Cycle pages.

Looking for more information about Dairyland? We have a few milestones we're proud of. See the nifty chart below.

Our Story
  • 1916 – The company begins to write auto insurance
    The Hardware Dealers Mutual Fire Insurance Company of Wisconsin begins writing auto insurance for its members. Previously, the company sold property & casualty insurance to Wisconsin Retail Hardware Association members. Today, that small business has grown and prospered to become Sentry Insurance, parent company of the Dairyland Insurance Company.
  • 1953 – Dairyland Insurance Company is formed
    Stuart Struck, a University of Wisconsin – Madison professor formed Dairyland Mutual Insurance Company of Wisconsin. The specialty auto insurance company insured drivers who, because of driving records, inexperience or lack of prior insurance, had difficulty obtaining insurance at standard rates.
  • 1966 – Sentry acquires the Dairyland Insurance Company

    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 bikes.

  • 1975 – Motorcycle insurance policies are sold through independent agents
    Motorcycle insurance policies are sold through Dairyland® independent agents. Sentry also introduces the Plain Talk car policy – the first policy in the industry written in everyday language.
  • 1975 – Sentry introduces the Plain Talk car policy
    Following a national poll, Sentry introduced the Plain Talk car policy – the first policy in the industry written in everyday language.
  • 1977 – Sentry moves into its new (and current) headquarters in Stevens Point, Wis.
    Sentry Insurance Headquarters
    Sentry Insurance moves into its new (and current) headquarters in Stevens Point, Wisconsin.
  • 1986 – Sentry introduces the Payback Auto policy

    Payback - man holding steering wheel 

    Former Green Bay Packers quarterback Bart Starr – who served on the Sentry Insurance board of directors for 34 years – helped introduce the Payback Auto policy, which rewarded claim-free policyholders.

  • 1992 – Sentry achieves an A+ rating from A.M. Best
    Sentry achieves an A+ financial strength rating from A.M. Best, which assures Dairyland® policyholders that we will be there when they need us.
  • 2004 – Sentry celebrates 100 years

    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®; merging operations with Dairyland doubled the size of Sentry's specialty auto niche
    Sentry acquires Viking Insurance®. Merging operations with Dairyland doubled the size of the company’s specialty auto niche and brought even more industry expertise aboard. Combined, the company wrote non-standard auto policies in 43 states.
  • 2016 – A milestone year for Dairyland and Sentry
    Dairyland celebrates insuring riders and their bikes for 50 years, while Sentry celebrates writing auto insurance for 100 years.
Pete Anhalt

Pete Anhalt

Senior Vice President

Message from Pete

Thank you for checking out DairylandInsurance.com for your insurance needs. You’ve come to the right spot for either automobile or motorcycle coverage. I’m confident you’ll find our dedicated staff can assist you with any questions you might have. If you need assistance, click on the “Contact Us” tab. There you’ll find phone numbers to call, or a form to send a message to one of our staff. We’re here to help you find the right coverage, make a claim or answer your policy questions.