Dairyland Insurance

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.

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.

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 moves into its new (and current) headquarters in Stevens Point, Wisconsin.

1992

Sentry is rated A+ (superior) by AM Best*

AM Best awards Sentry an A+ Financial Strength Rating (FSR)—a rating we’ve earned every year since—assuring Dairyland policyholders we’ll be there when they need us. AM Best assigns an A+ FSR to insurance companies they believe have a superior ability to meet ongoing insurance obligations.

2004

Our centennial

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.

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