Updated May 2026
Best Trucking Companies in Oshkosh, Wisconsin (May 2026)
Lanefinder is tracking 334 W2 trucking carriers in Oshkosh, Wisconsin (May 2026). KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. 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 May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Oshkosh, Wisconsin's top trucking carriers right now
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 leads the Oshkosh, Wisconsin market on combined pay and ranking score this month. KEEP TRUCKING LLC pays above the 90th percentile on weekly pay for the Oshkosh, Wisconsin market. KEEP TRUCKING LLC's top FMCSA dimension is controlled-substances compliance, in the 88th percentile. Lanefinder's application data flags KEEP TRUCKING LLC as a responsive employer.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 97th percentile across Oshkosh, Wisconsin. True Transport Inc.'s FMCSA score is strongest on unsafe-driving avoidance — 99th percentile. True Transport Inc. responds to driver applications more reliably than the Oshkosh, Wisconsin median.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC pays above the 90th percentile on weekly pay for the Oshkosh, Wisconsin market. JK MOVING & STORAGE INC ranks in the 94th percentile for unsafe-driving avoidance on FMCSA SAFER data.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #6 PREMIER TRANSPORTATION at $1,700/wk, #7 KEN GRAHAM TRUCKING INC at $2,000/wk, #8 Badger Express LLC at $1,700/wk, #9 Diaz Stone & Pallet Inc. at $1,750/wk, #10 DIVINE ENTERPRISES at $1,375/wk.
Lane mix and benefits across Oshkosh, Wisconsin
The route mix in Oshkosh, Wisconsin this month tilts OTR: 19% regional, 76% OTR, 4% local, 1% semi-local — drawn from active postings, not historical surveys.
Across Oshkosh, Wisconsin CDL postings: 1% with guaranteed pay, 25% dedicated, 81% take-truck-home, 66% pet-friendly, 67% riders-allowed.
Oshkosh, Wisconsin vs Wisconsin: the numbers that diverge
Among the figures above, riders-allowed policies is where Oshkosh, Wisconsin differs most from Wisconsin — 5 points above statewide.
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 owner-operator companies in Oshkosh, Wisconsin
- CDL driver salary in Oshkosh, Wisconsin
- Best trucking companies in Wisconsin
Where this data comes from
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 May 2026.