Updated November 2026
Best Trucking Companies in Brookfield, Wisconsin (November 2026)
363 W2 trucking carriers are currently posting jobs in Brookfield, Wisconsin as of November 2026. 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 Brookfield, Wisconsin. Biggest climbs: Herrington Transportation Inc. (#35 → #1) and True Transport Inc. (#15 → #3). Biggest falls: LAWRENCE TRANSPORTATION COMPANY (#2 → #24) and K-WAY EXPRESS INC (#24 → #34). Elsewhere in the top 50, 5 carriers joined, 8 left, and 36 changed rank.
All changes since October 2026
Where CDL pay is strongest in Brookfield, 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. is number-one in Brookfield, Wisconsin this month on the composite ranking. The carrier ranks in the 91st percentile for weekly pay in Brookfield, Wisconsin. Application-response data flags this carrier as a responsive employer.
#2South East Carriers INC — $1,800/wk
South East Carriers INC ranks in the 96th percentile for controlled-substances compliance on FMCSA SAFER data. Driver applications get a faster-than-median response in Brookfield, Wisconsin.
#3True Transport Inc. — $2,250/wk
True Transport Inc. climbed from #15 to #3 this month — one of the biggest moves in Brookfield, Wisconsin. Pay sits above the 92nd percentile in the Brookfield, 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 MNS1 EXPRESS INC at $2,050/wk, #9 HandledNow LLC at $1,550/wk, #10 Covenant Transport Inc at $1,762/wk.
Lane mix and benefits across Brookfield, Wisconsin
Of active CDL postings in Brookfield, Wisconsin this month, 21% are regional and 72% are OTR (long-haul). Local and semi-local routes account for the remaining 7%.
Across Brookfield, Wisconsin CDL postings: 3% with guaranteed pay, 25% dedicated, 78% take-truck-home, 64% pet-friendly, 64% riders-allowed.
How Brookfield, Wisconsin compares to Wisconsin
| Brookfield, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Dedicated routes | 34% | 41% | -7 pt |
| Pet-friendly fleets | 68% | 63% | +5 pt |
Source: Lanefinder index, November 2026
The largest gap is on dedicated routes: Brookfield, Wisconsin sits 7 points below 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 Brookfield, Wisconsin
- CDL driver salary in Brookfield, 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 November 2026.