50+ A-rated carriers shopping your rate. 1,400+ active policies. Bilingual EN/ES. Free quotes in 2 hours. Hard-to-place welcome — accidents, violations, new MC, international licenses.
Portland is the largest commercial trucking hub in the Pacific Northwest. With the Port of Portland handling Pacific Rim container freight, the I-5 / I-84 / I-205 corridors connecting Seattle to Los Angeles and the Columbia Gorge to the Midwest, and the dense industrial belt along Marine Drive and Rivergate, Portland-based owner-operators handle everything from port drayage to long-haul I-5 lanes to specialized agricultural transport from the Willamette Valley. The PDX cargo complex and the booming Hillsboro tech-manufacturing corridor add additional freight demand. Checkers Truck Insurance Services writes Portland policies — from owner-operators running drayage out of Terminal 6 to fleets serving the Columbia River industrial corridor.
We currently maintain over 1,400 active policies across California, Texas, and Oregon, hold a 4.9/5 rating from 127+ trucker reviews, and shop 50+ A-rated carriers for every quote — including Progressive, Great American, Berkshire Hathaway GUARD, CNA, Lloyd's of London, Cover Whale, and AmTrust.
Independent broker. Portland-area expertise. Real underwriting relationships.
Established 2009. We know how Portland risks underwrite, what carriers want, and how to get you priced.
Progressive, Great American, Berkshire Hathaway GUARD, CNA, Lloyd's, Cover Whale, AmTrust — we shop them all.
Quote, bind, claims, renewals — all in English or Spanish. Hablamos tu idioma.
Standard accounts quoted within 2 business hours. Same-day binding once paperwork clears.
Every line a working trucker actually needs — packaged for owner-operators through fleets.
Primary liability up to $1M+. Required by FMCSA for interstate commerce.
Protects the freight you're hauling. Customizable limits for dry van, reefer, flatbed, and high-value loads.
Covers your tractor and trailer for collision, theft, fire, and weather damage.
Premises and operations coverage — required by most shippers and brokers.
Covers non-owned trailers you pull under interchange agreement.
Bobtail coverage for when you're operating off-dispatch.
Most brokers can't write you. We can — because hard-to-place is what we do.
We have surplus-lines markets — including Lloyd's of London syndicates and specialty carriers like Cover Whale — that exist specifically to write port drayage, intermodal, long-haul I-5, agricultural transport, and dedicated regional that standard markets won't touch. We package your submission so underwriters see the full story, not just the loss runs.
Fill the form. A Portland-area specialist calls you back within 2 hours with rates from 50+ carriers.
Free. No obligation. Bilingual agents available.
Portland owner-operators with clean MVRs typically pay $9,000–$16,500 per year in 2026. Fleet rates run $7,000–$12,500 per truck annually. Port drayage and refrigerated long-haul price at the upper end. Call Checkers at (909) 824-6500 for an exact quote.
Yes. Port of Portland drayage is a routine placement for us. Multiple A-rated carriers have appetite for Terminal 6 operations, including for new MC numbers and accounts with prior claims.
Yes. Hard-to-place risks — including recent accidents, multiple violations, and prior cancellations — are a Checkers specialty. We have surplus-lines markets that write Portland-area drivers when standard markets won't.
Sí. Fully bilingual EN/ES team. Quotes, binding, claims, renewals — all in either language. Hablamos español. Llame al (909) 824-6500.
Standard Portland accounts are quoted within 2 business hours. Hard-to-place accounts take 24–48 hours. Same-day binding once paperwork and down payment clear.
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Join 1,400+ truckers across the Western US who trust Checkers.
Get Free Quote →🇲🇽 Hablamos español — llame al (909) 824-6500 para una cotización gratis.