Wisconsin’s Trusted Trucking Insurance Experts

We Know Trucking & Insurance Inside and Out!

 

Trucking is a cornerstone of Wisconsin’s economy, and we understand how crucial it is to keep your business moving. Whether you’re hauling freight through Milwaukee, navigating I-94, or making local deliveries, you need insurance that works as hard as you do.

At Charles Cain Group, we specialize in trucking insurance right here in Wisconsin. We know the ins and outs of the industry, from DOT compliance to state-specific coverage requirements. Whether you're an owner-operator, managing a small fleet, or running a large trucking company, we have the expertise to keep you protected.

​

Comprehensive Coverage for Wisconsin Truckers

✔ Auto Liability – Coverage to protect you on the road.
✔ Motor Truck Cargo – Ensures your freight is covered in case of loss or damage.
✔ General Liability – Protects your business from legal claims.
✔ Physical Damage – Safeguards your truck and trailer from accidents and theft.
✔ Bobtail Insurance – Coverage for non-dispatch driving.
✔ Intermodal Hauling – Specialized coverage for drayage and container transport.
✔ Non-Trucking Liability – Protection for personal use of your truck.

​

While You Take in Wisconsin’s Beauty, We’re Hard at Work for You

Whether you’re cheering for the Green Bay Packers, exploring the beauty of the Wisconsin Dells, or enjoying the local flavors of a cheese festival, we’re working behind the scenes to make sure your business stays protected. While you take time to enjoy the best of Wisconsin, we’re securing the right coverage to keep you on the road.

​

Why Wisconsin Truckers Trust Us

• Local Expertise: We know Wisconsin trucking regulations inside and out.

• Custom Solutions: Your business is unique—your coverage should be too.

• Fast, Reliable Service: We get you covered quickly so you can focus on driving.

• DOT & Compliance Support: Stay ahead of state and federal requirements.

​

Let’s Talk About Your Coverage Needs

Your truck is more than just a vehicle—it’s your livelihood. Don’t risk being underinsured. Whether you're looking for better coverage, need help understanding Wisconsin trucking insurance, or just want expert advice, we’re here to help.

​

📅 Book a Consultation Today!  Ready to Quote?  Click here to go to our quote submission page!