Updated September 2026
Best Trucking Companies in Sheboygan, Wisconsin (September 2026)
Lanefinder is tracking 322 W2 trucking carriers in Sheboygan, Wisconsin (September 2026). WESTERN MOUNTAIN TRANSPORT INC leads with an average weekly pay of $1,700 and an average $5,000 sign-on bonus. South East Carriers INC follows at $1,800/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 September 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 WESTERN MOUNTAIN TRANSPORT INC at $1,700/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1WESTERN MOUNTAIN TRANSPORT INC — $1,700/wk
WESTERN MOUNTAIN TRANSPORT INC leads the Sheboygan, Wisconsin market on combined pay and ranking score this month. Top FMCSA dimension here is driver fitness, in the 93rd percentile. Application-response data flags this carrier as a responsive employer.
#2South East Carriers INC — $1,800/wk
South East Carriers INC's FMCSA score is strongest on driver fitness — 93rd percentile. Application-response data flags this carrier as a responsive employer.
#3PREMIER TRANSPORTATION — $1,950/wk
PREMIER TRANSPORTATION's weekly pay ranks in the 87th percentile across Sheboygan, Wisconsin. PREMIER TRANSPORTATION ranks in the 98th percentile for driver fitness on FMCSA SAFER data.
Also in the top 10: #4 JK MOVING & STORAGE INC at $2,200/wk, #5 Covenant Transport Inc at $1,762/wk, #6 TDR TRANSPORT at $2,200/wk, #7 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #8 Badger Express LLC at $1,700/wk, #9 C & G TRANSPORTATION INC at $2,000/wk, #10 Diaz Stone & Pallet Inc. at $1,750/wk.
What Sheboygan, Wisconsin drivers actually run
Of active CDL postings in Sheboygan, Wisconsin this month, 21% are regional and 75% are OTR (long-haul). Local and semi-local routes account for the remaining 4%.
Guaranteed pay is on offer at 2% of Sheboygan, Wisconsin postings; dedicated routes at 24%; take-truck-home at 81%. Pet-friendly policies appear at 68% and riders-allowed at 68%.
How Sheboygan, Wisconsin compares to Wisconsin
| Sheboygan, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 42% | 37% | +5 pt |
| Pet-friendly fleets | 76% | 67% | +9 pt |
| Riders-allowed policies | 80% | 73% | +7 pt |
Source: Lanefinder index, September 2026
The largest gap is on pet-friendly fleets: Sheboygan, Wisconsin sits 9 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 September 2026.