Updated September 2026
Best Owner-Operator Companies in Oshkosh, Wisconsin (September 2026)
586 owner-operator carriers are hiring in Oshkosh, Wisconsin this 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. Wisconsin freight moves on I-90 / I-94 through Milwaukee and Madison, with dairy and food processing as the dominant outbound commodity and paper and packaging manufacturing in the Fox River Valley generating consistent industrial loads.
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 Oshkosh, Wisconsin compares to Wisconsin
| Oshkosh, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,600 | $5,277 | +25% |
| Riders-allowed policies | 90% | 80% | +10 pt |
Source: Lanefinder index, September 2026
Among the figures above, average weekly pay is where Oshkosh, Wisconsin differs most from Wisconsin — 25% above statewide.
Oshkosh, Wisconsin's top owner-operator carriers right now
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 tops the Oshkosh, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. Gross weekly revenue here lands in the 94th percentile across Oshkosh, Wisconsin. Strongest FMCSA dimension is driver fitness — 87th percentile. RAY'S TRANSPORT INC tracks as a responsive employer on application-response data.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
#3WESTERN MOUNTAIN TRANSPORT INC — $8,750/wk
WESTERN MOUNTAIN TRANSPORT INC pays above the 90th percentile on gross weekly revenue for the Oshkosh, Wisconsin market. Strongest FMCSA dimension is driver fitness — 93rd percentile. Application-response data flags this carrier as a responsive employer.
Also in the top 10: #4 LOAD MONSTER INC at $5,125/wk, #5 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #6 SWEET EXPRESS LLC at $8,500/wk, #7 WIDER GROUP INC at $6,250/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 Ali Star Inc at $10,000/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
What Oshkosh, Wisconsin drivers actually run
Of active CDL postings in Oshkosh, Wisconsin this month, 7% are regional and 92% are OTR (long-haul). Local and semi-local routes account for the remaining 1%.
Guaranteed pay is on offer at 2% of Oshkosh, Wisconsin postings; dedicated routes at 27%; take-truck-home at 93%. Pet-friendly policies appear at 74% and riders-allowed at 71%.
Driving CDL in Wisconsin
Wisconsin freight moves on I-90 / I-94 through Milwaukee and Madison. Dairy and food processing are dominant outbound commodities — Wisconsin's reefer freight is a national-scale segment. Paper and packaging manufacturing in the Fox River Valley generates consistent industrial loads. Great Lakes ports at Green Bay and Superior handle bulk cargo. Cost of living is moderate. Wisconsin has a high graduated state income tax. Winter is severe — lake-effect snow off Lake Michigan affects the eastern third of the state; ice and salt corrosion eat equipment faster than southern states.
Related guides
- Best trucking companies in Oshkosh, Wisconsin
- CDL driver salary in Oshkosh, Wisconsin
- Best owner-operator companies in Wisconsin
The methodology behind the rankings
Compensation (30%): pay percentile + sign-on bonus + guaranteed pay + settlement frequency. FMCSA safety (25%): weighted percentile across vehicle maintenance, unsafe driving, hours-of-service, driver fitness, and controlled substances. Benefits (25%): hiring-type-aware. Operational (20%): driver-application responsiveness, modulated by fleet scale. Updated September 2026.