Updated November 2026
Best Trucking Companies in Kenosha, Wisconsin (November 2026)
385 W2 trucking carriers are hiring in Kenosha, Wisconsin this November 2026. Herrington Transportation Inc. leads with an average weekly pay of $2,000. FW TRUCKING 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 November 2026
McLeod Express LLC at #4, SAFE WAY CARRIER LLC at #6, and MNS1 EXPRESS INC at #9 are new to the top 50 in Kenosha, Wisconsin. Biggest climbs: Herrington Transportation Inc. (#35 → #1), FW TRUCKING (#17 → #2), and True Transport Inc. (#13 → #3). Biggest fall: LAWRENCE TRANSPORTATION COMPANY (#1 → #23). Elsewhere in the top 50, 5 carriers joined, 8 left, and 34 changed rank.
All changes since October 2026
The trucking companies leading Kenosha, Wisconsin this month
The top of the list is Herrington Transportation Inc. at $2,000/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1Herrington Transportation Inc. — $2,000/wk
Herrington Transportation Inc. leads the Kenosha, Wisconsin market on combined pay and ranking score this month. Herrington Transportation Inc.'s weekly pay ranks in the 91st percentile across Kenosha, Wisconsin. Herrington Transportation Inc. tracks as a responsive employer on application-response data.
#2FW TRUCKING — $1,800/wk
FW TRUCKING climbed from #17 to #2 this month — one of the biggest moves in Kenosha, Wisconsin. On unsafe-driving avoidance, the carrier ranks in the 90th percentile per FMCSA SAFER data.
#3True Transport Inc. — $2,250/wk
True Transport Inc. is up from #13 last month, one of the largest jumps in the Kenosha, Wisconsin ranking. Pay sits above the 92nd percentile in the Kenosha, Wisconsin market. True Transport Inc.'s top FMCSA dimension is unsafe-driving avoidance, in the 98th percentile.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
Also in the top 10: #4 McLeod Express LLC at $1,483/wk, #5 PREMIER TRANSPORTATION at $1,950/wk, #6 SAFE WAY CARRIER LLC at $2,100/wk, #7 JK MOVING & STORAGE INC at $2,200/wk, #8 HandledNow LLC at $1,550/wk, #9 MNS1 EXPRESS INC at $2,050/wk, #10 Covenant Transport Inc at $1,762/wk.
Lane mix and benefits across Kenosha, Wisconsin
20% of Kenosha, Wisconsin's active CDL postings are regional and 67% are OTR; local plus semi-local accounts for the rest (13%).
Across Kenosha, Wisconsin CDL postings: 3% with guaranteed pay, 27% dedicated, 74% take-truck-home, 60% pet-friendly, 61% riders-allowed.
How Kenosha, Wisconsin compares to Wisconsin
Among the figures above, dedicated routes is where Kenosha, Wisconsin differs most from Wisconsin — 9 points below 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 Kenosha, Wisconsin
- CDL driver salary in Kenosha, Wisconsin
- Best trucking companies in Wisconsin
Where this data comes from
Compensation, FMCSA safety, benefits, and operational performance — weighted 30, 25, 25, and 20 percent respectively. Compensation extends beyond headline pay to include sign-on bonus tier and settlement cadence. Benefits scoring differs by hiring type because the perks that matter to a W2 driver and a contractor are not the same. Updated November 2026.