Updated May 2026
Best Trucking Companies in Lake Oswego, Oregon (May 2026)
241 W2 trucking carriers are currently posting jobs in Lake Oswego, Oregon as of May 2026. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. Oregon freight moves on I-5 north-south through Portland and Eugene, with the Port of Portland handling bulk grain and auto imports, and agricultural and forestry exports — wheat, hay, lumber — generating significant outbound volumes.
What changed in May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Where CDL pay is strongest in Lake Oswego, Oregon this month
The top of the list is KEEP TRUCKING LLC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1KEEP TRUCKING LLC — $2,200/wk
KEEP TRUCKING LLC is number-one in Lake Oswego, Oregon this month on the composite ranking. KEEP TRUCKING LLC sits in the 95th percentile for weekly pay among Lake Oswego, Oregon carriers. On controlled-substances compliance, the carrier ranks in the 88th percentile per FMCSA SAFER data. Driver applications get a faster-than-median response in Lake Oswego, Oregon.
#2True Transport Inc. — $2,250/wk
True Transport Inc. pays above the 92nd percentile on weekly pay for the Lake Oswego, Oregon market. On unsafe-driving avoidance, the carrier ranks in the 99th percentile per FMCSA SAFER data. Driver applications get a faster-than-median response in Lake Oswego, Oregon.
#3DICK IRVIN INC — $2,250/wk
DICK IRVIN INC's weekly pay ranks in the 97th percentile across Lake Oswego, Oregon. DICK IRVIN INC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data.
DICK IRVIN INC offers the highest sign-on bonus among Lake Oswego, Oregon's top 10 — $10,000.
Also in the top 10: #4 JK MOVING & STORAGE INC at $2,200/wk, #5 SABUR LLC at $1,850/wk, #6 ORGANICALLY GROWN COMPANY at $2,350/wk, #7 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #8 DIVINE ENTERPRISES at $1,375/wk, #9 OAK HARBOR FREIGHT LINES INC at $1,750/wk, #10 Dillard Trucking at $2,200/wk.
What Lake Oswego, Oregon drivers actually run
Of active CDL postings in Lake Oswego, Oregon this month, 18% are regional and 72% are OTR (long-haul). Local and semi-local routes account for the remaining 10%.
Across Lake Oswego, Oregon CDL postings: 1% with guaranteed pay, 26% dedicated, 74% take-truck-home, 63% pet-friendly, 62% riders-allowed.
Driving CDL in Oregon
Oregon freight moves on I-5 north-south through the Willamette Valley (Portland-Salem-Eugene), with the Port of Portland handling bulk grain (one of the largest US wheat-export terminals) and auto imports. Agricultural and forestry exports — wheat, hay, lumber, Christmas trees in season — generate significant outbound volume. Mountain passes on I-84 east and on US-26 west of Mt. Hood are winter operational variables. Oregon has no general sales tax but a high graduated state income tax. Cost of living in Portland is high; rural OR is more affordable.
Related guides
- Best owner-operator companies in Lake Oswego, Oregon
- CDL driver salary in Lake Oswego, Oregon
- Best trucking companies in Oregon
Where this data comes from
Lanefinder's ranking algorithm weights compensation at 30%, FMCSA SAFER safety at 25%, benefits at 25%, and operational performance at 20%. Compensation reflects pay percentile plus sign-on bonus, guaranteed pay, and settlement-frequency adjustments. Benefits scoring is hiring-type-aware. Operational performance comes mostly from how carriers handle real driver applications. Updated May 2026.