Updated July 2026
Best Owner-Operator Companies in Oshkosh, Wisconsin (July 2026)
582 owner-operator carriers are hiring in Oshkosh, Wisconsin this July 2026. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $5,500. INLAND EMPIRE LLC follows at $7,875/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 July 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 | $6,716 | $5,295 | +27% |
| Riders-allowed policies | 88% | 78% | +10 pt |
Source: Lanefinder index, July 2026
Among the figures above, average weekly pay is where Oshkosh, Wisconsin differs most from Wisconsin — 27% above statewide.
Oshkosh, Wisconsin's top owner-operator carriers right now
The top of the list is ROLLING ON WHEELS LLC at $5,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $5,500/wk
ROLLING ON WHEELS LLC leads the Oshkosh, Wisconsin market on combined gross revenue and ranking score this month. On driver fitness, the carrier ranks in the 96th percentile per FMCSA SAFER data. ROLLING ON WHEELS LLC responds to driver applications more reliably than the Oshkosh, Wisconsin median.
#2INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 84th percentile on gross weekly revenue for the Oshkosh, Wisconsin market.
#3WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 SWEET EXPRESS LLC at $8,500/wk, #6 OVERLOG INC at $3,613/wk, #7 WIDER GROUP INC at $6,250/wk, #8 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 BB8 FREIGHT CO at $12,666/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 93% are OTR (long-haul). Local and semi-local routes account for the remaining 0%.
Guaranteed pay is on offer at 2% of Oshkosh, Wisconsin postings; dedicated routes at 26%; take-truck-home at 94%. Pet-friendly policies appear at 75% 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 July 2026.