Rachael Brennan has been working in the insurance industry since 2006 when she began working as a licensed insurance representative for 21st Century Insurance, during which time she earned her Property and Casualty license in all 50 states. After several years she expanded her insurance expertise, earning her license in Health and AD&D insurance as well. She has worked for small health insuran...

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Chris Harrigan has an economic degree from Limestone College and an MBA from Clemson University. He previously managed auto insurance claims for Enterprise Rent-A-Car. Currently, he is using his business and insurance expertise to provide insurance data analysis and visualizations to enhance the user experience.

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Reviewed by Chris Harrigan
Former Auto Insurance Claims Manager

UPDATED: Aug 10, 2021

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Key takeaways...

  • Dairyland Car Insurance has been known as a leader in the motorcycle and auto insurance industry for years
  • Sentry Insurance Group is based out of Stevens Point, Wisconsin
  • They offer insurance products for individuals as well as for businesses

This Dairyland Car Insurance Review will discuss briefly Dairyland Insurance and more about the company it is a part of, Sentry Insurance. Dairyland Insurance is a subsidiary of the Sentry Insurance Group. Their site advertises a trusted broker for personal auto insurance, motorcycle insurance, and off-road vehicle insurance.

It has become a leader in the industry due to the money-saving discounts, competitive rates, and options for flexible payments. This includes SR-22 and other high-cost high-risk policies. A broker can work with different underwriters to find an insurance quote that makes sense. Ultimately, the goal is to find an insurance policy personalized to each driver.

To compare car insurance quotes, enter your zip code above to get started for FREE!

Who is Sentry Insurance?

Sentry Insurance Group is based out of Stevens Point, Wisconsin. It offers insurance products for individuals as well as for businesses.

Sentry Insurance is the underwriter for many different companies, so if Dairyland Insurance is not located in your area, there may be a different company around you that is affiliated with Sentry. They offer things like a multi-policy or defensive driving discount. The great thing about having an agent on your side is they can seek out these opportunities you might otherwise miss.

Besides auto insurance, Sentry also offers insurance products include:

  • Motorcycles
  • Renters
  • Homeowners
  • Recreational vehicles
  • Boats
  • Personal liability umbrella
  • Rental property
  • Life insurance

Their website explains more in detail what each insurance product is for and has a section for frequently asked questions.

If you ever have a claim, Sentry has someone available 24 hours a day, 7 days a week to take your call and walk you through the steps you need to take to file and process the claim.

If you would like to search for a car insurance company right now, just enter your zip code below and you can compare car insurance quotes!


  1. https://www.allstate.com/renters-insurance.aspx
  2. https://www.geico.com/homeowners-insurance/
  3. https://www.geico.com/information/aboutinsurance/umbrella/