Trucking Insurance · Madison, WI
Madison sits at the intersection of I-90 and I-39 — a key freight crossroads for Wisconsin and the broader Midwest. Drivers running out of Madison handle everything from agricultural products and dairy to manufactured goods moving east-west across the state. We provide specialty trucking insurance for Madison-area owner-operators and small carriers with access to markets that understand Wisconsin freight.
What’s Covered
Every trucking operation is different. We work with specialty markets to put together coverage that matches what you actually haul, where you run, and how you operate.
Required by the FMCSA for interstate operations. Covers bodily injury and property damage you cause to others while under dispatch. Minimum limits vary by commodity — we make sure yours meet federal and shipper requirements.
Covers your truck and trailer against collision, fire, theft, vandalism, and weather damage. Includes both collision and comprehensive coverage, with deductible options to fit your budget.
Covers the freight you're hauling against damage or loss while in your care, custody, and control. Most brokers and shippers require at least $100,000 in cargo coverage.
Covers you when you're driving your tractor without a trailer, or for personal use outside a dispatch. A common gap for owner-operators leased to a carrier.
A more affordable alternative to workers' comp for owner-operators who don't qualify for traditional workers' comp. Covers medical expenses and lost income from on-the-job injuries.
Covers claims arising from your business operations that aren't related to a vehicle accident — loading/unloading incidents, premises liability, and more.
Why Dayton Insurance
We work with carriers that specialize in commercial trucking — not standard auto insurers trying to fit trucks into a personal lines box. That means better rates and real coverage for your operation.
As an independent agency, we compare quotes from multiple trucking specialty markets to find your best combination of price, coverage, and service.
We're licensed in Minnesota, Wisconsin, Colorado, and Nevada — ideal for drivers who cross state lines or operate regionally across the Midwest and Mountain West.
Ready when you are
Tell us what you’re hauling, where you run, and we’ll get back to you with options from multiple specialty carriers. Most quotes back within one business day.
Common Questions
Ag haulers in Wisconsin typically need primary liability, cargo coverage (limits depend on commodity value), and physical damage for the truck and trailer. Some specialty ag commodities like grain or livestock have specific coverage considerations. We work with markets experienced in agricultural freight.
Yes — an FMCSA-compliant policy covers you in all states while under dispatch. Your primary liability, cargo, and other coverages follow you across state lines. We make sure your policy meets federal minimums regardless of where your lanes take you.
Almost certainly yes. When you're leased to a carrier, their policy covers you while under dispatch — but NOT when you're driving bobtail (without a trailer) or using the truck outside of dispatch. Bobtail coverage fills that gap and is typically very affordable.
Call or text (651) 243-0056, or fill out the form on this page. We'll ask about your commodities, lanes, equipment, and driving record — then shop specialty markets to find your best rate. Most quotes back within one business day.
