Updated May 2026
Best Trucking Companies in Sheboygan, Wisconsin (May 2026)
Lanefinder is tracking 327 W2 trucking carriers in Sheboygan, 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.
Sheboygan, 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 is number-one in Sheboygan, Wisconsin this month on the composite ranking. The carrier ranks in the 95th percentile for weekly pay in Sheboygan, Wisconsin. Strongest FMCSA dimension is controlled-substances compliance — 88th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 97th percentile across Sheboygan, Wisconsin. Top FMCSA dimension here is unsafe-driving avoidance, in the 99th percentile. True Transport Inc. tracks as a responsive employer on application-response data.
For pure pay maximization, True Transport Inc. beats the #1-ranked carrier weekly at $2,250.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC pays above the 90th percentile on weekly pay for the Sheboygan, Wisconsin market. JK MOVING & STORAGE INC's top FMCSA dimension is unsafe-driving avoidance, in the 94th percentile.
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.
What Sheboygan, Wisconsin drivers actually run
Of active CDL postings in Sheboygan, Wisconsin this month, 20% are regional and 76% are OTR (long-haul). Local and semi-local routes account for the remaining 4%.
Guaranteed pay is on offer at 1% of Sheboygan, Wisconsin postings; dedicated routes at 24%; take-truck-home at 81%. Pet-friendly policies appear at 66% and riders-allowed at 66%.
How Sheboygan, Wisconsin compares to Wisconsin
| Sheboygan, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Pet-friendly fleets | 74% | 67% | +7 pt |
| Riders-allowed policies | 78% | 73% | +5 pt |
Source: Lanefinder index, May 2026
The largest gap is on pet-friendly fleets: Sheboygan, Wisconsin sits 7 points above the Wisconsin baseline.
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 Sheboygan, Wisconsin
- CDL driver salary in Sheboygan, Wisconsin
- Best trucking companies in Wisconsin
Where this data comes from
Carriers are scored against carriers in their own market. The composite is 30% compensation (pay + bonus + guaranteed pay + settlement cadence), 25% FMCSA safety, 25% benefits (W2 vs owner-op scoring), and 20% operational performance (responsiveness + fleet scale). No paid placement — the weights are the same for every carrier in the index. Updated May 2026.