Updated September 2026
Best Owner-Operator Companies in Owensboro, Kentucky (September 2026)
Lanefinder is tracking 638 owner-operator carriers in Owensboro, Kentucky (September 2026). RAY'S TRANSPORT INC leads with an average gross weekly revenue of $8,500 and an average $2,000 sign-on bonus. WINNERS TRANSPORTATION LLC follows at $2,657/week gross. Kentucky is home to UPS Worldport in Louisville, the largest air cargo sort facility in the US, with I-65 / I-71 / I-75 truck corridors feeding automotive assembly plants and a major bourbon-export manufacturing cluster.
What changed in September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
How Owensboro, Kentucky compares to Kentucky
| Owensboro, Kentucky | Kentucky top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,089 | $5,465 | +11% |
| Dedicated routes | 42% | 36% | +6 pt |
| Riders-allowed policies | 92% | 86% | +6 pt |
Source: Lanefinder index, September 2026
Among the figures above, average weekly pay is where Owensboro, Kentucky differs most from Kentucky — 11% above statewide.
Where owner-operator pay is strongest in Owensboro, Kentucky this month
The top of the list is RAY'S TRANSPORT INC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1RAY'S TRANSPORT INC — $8,500/wk
RAY'S TRANSPORT INC leads the Owensboro, Kentucky market on combined gross revenue and ranking score this month. Pay sits above the 90th percentile in the Owensboro, Kentucky market. RAY'S TRANSPORT INC's FMCSA score is strongest on driver fitness — 87th percentile. RAY'S TRANSPORT INC responds to driver applications more reliably than the Owensboro, Kentucky median.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. Application-response data flags this carrier as a responsive employer.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #6 WIDER GROUP INC at $6,250/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 AIA TRUCKING INC at $3,450/wk, #9 M&D TRANSPORT at $7,000/wk, #10 JK MOVING & STORAGE INC at $4,975/wk.
Lane mix and benefits across Owensboro, Kentucky
Of active CDL postings in Owensboro, Kentucky this month, 9% are regional and 90% are OTR (long-haul). Local and semi-local routes account for the remaining 1%.
Across Owensboro, Kentucky CDL postings: 2% with guaranteed pay, 27% dedicated, 93% take-truck-home, 73% pet-friendly, 70% riders-allowed.
Driving CDL in Kentucky
Kentucky is home to UPS Worldport in Louisville, the largest air cargo sort facility in the US, which generates enormous regional trucking demand around the nightly sort cycle. The I-65 / I-71 / I-75 corridors feed automotive assembly (Toyota Georgetown, Ford Louisville) and bourbon distillery distribution. Coal freight from eastern KY mines runs east-west to power plants and rail terminals. Cost of living is below the national average. Kentucky has a low flat state income tax. I-75 through the eastern KY mountains in winter is no joke.
Related guides
- Best trucking companies in Owensboro, Kentucky
- CDL driver salary in Owensboro, Kentucky
- Best owner-operator companies in Kentucky
How we compile these rankings
Pay carriers against each other within the same market (30%). Layer a weighted FMCSA SAFER safety percentile on top (25%). Score the benefits package against what actually matters for the hiring type — W2 health/financial benefits or owner-op operational perks (25%). Finish with operational performance: responsiveness to driver applications plus fleet scale (20%). All percentiles are recomputed monthly. Updated September 2026.