Updated November 2026
Best Trucking Companies in Waukesha, Wisconsin (November 2026)
In Waukesha, Wisconsin as of November 2026, 366 carriers are actively hiring W2 company drivers. Herrington Transportation Inc. leads with an average weekly pay of $2,000. 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 November 2026
McLeod Express LLC at #4, SAFE WAY CARRIER LLC at #6, and MNS1 EXPRESS INC at #8 are new to the top 50 in Waukesha, Wisconsin. Biggest climbs: Herrington Transportation Inc. (#36 → #1) and True Transport Inc. (#15 → #3). Biggest fall: LAWRENCE TRANSPORTATION COMPANY (#2 → #25). Elsewhere in the top 50, 5 carriers joined, 8 left, and 35 changed rank.
All changes since October 2026
Waukesha, Wisconsin's top trucking carriers right now
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. is number-one in Waukesha, Wisconsin this month on the composite ranking. Herrington Transportation Inc.'s weekly pay ranks in the 91st percentile across Waukesha, Wisconsin. The carrier tracks as a responsive employer on Lanefinder's data.
#2South East Carriers INC — $1,800/wk
South East Carriers INC's top FMCSA dimension is controlled-substances compliance, in the 96th percentile. South East Carriers INC responds to driver applications more reliably than the Waukesha, Wisconsin median.
#3True Transport Inc. — $2,250/wk
True Transport Inc. is up from #15 last month, one of the largest jumps in the Waukesha, Wisconsin ranking. True Transport Inc. pays above the 92nd percentile on weekly pay for the Waukesha, Wisconsin market. On unsafe-driving avoidance, the carrier ranks in the 98th percentile per FMCSA SAFER data.
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 MNS1 EXPRESS INC at $2,050/wk, #9 HandledNow LLC at $1,550/wk, #10 Covenant Transport Inc at $1,762/wk.
What Waukesha, Wisconsin drivers actually run
21% of Waukesha, Wisconsin's active CDL postings are regional and 71% are OTR; local plus semi-local accounts for the rest (8%).
Across Waukesha, Wisconsin CDL postings: 2% with guaranteed pay, 25% dedicated, 78% take-truck-home, 64% pet-friendly, 64% riders-allowed.
Waukesha, Wisconsin vs Wisconsin: the numbers that diverge
| Waukesha, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 40% | 35% | +5 pt |
| Dedicated routes | 34% | 41% | -7 pt |
| Pet-friendly fleets | 68% | 63% | +5 pt |
Source: Lanefinder index, November 2026
Among the figures above, dedicated routes is where Waukesha, Wisconsin differs most from Wisconsin — 7 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 Waukesha, Wisconsin
- CDL driver salary in Waukesha, Wisconsin
- Best trucking companies in Wisconsin
Where this data comes from
The score is built from four buckets. Thirty percent compensation, drawn from real active job postings and modified by bonus and settlement structure. Twenty-five percent safety, from FMCSA SAFER. Twenty-five percent benefits, scored hiring-type-aware. Twenty percent operational performance, drawn from how carriers actually behave toward applicants. Updated November 2026.