Updated November 2026
Best Trucking Companies in Greenfield, Wisconsin (November 2026)
Through November 2026, 366 carriers in Greenfield, Wisconsin employ W2 company drivers across the lanes Lanefinder tracks. Herrington Transportation Inc. leads with an average weekly pay of $2,000. 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 November 2026
McLeod Express LLC at #3, SAFE WAY CARRIER LLC at #5, and MNS1 EXPRESS INC at #7 are new to the top 50 in Greenfield, Wisconsin. Biggest climbs: Herrington Transportation Inc. (#35 → #1) and True Transport Inc. (#14 → #2). Biggest fall: LAWRENCE TRANSPORTATION COMPANY (#1 → #24). Elsewhere in the top 50, 5 carriers joined, 8 left, and 35 changed rank.
All changes since October 2026
Where CDL pay is strongest in Greenfield, 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. tops the Greenfield, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. Weekly pay here lands in the 91st percentile across Greenfield, Wisconsin. Herrington Transportation Inc. tracks as a responsive employer on application-response data.
#2True Transport Inc. — $2,250/wk
True Transport Inc. climbed from #14 to #2 this month — one of the biggest moves in Greenfield, Wisconsin. True Transport Inc. pays above the 92nd percentile on weekly pay for the Greenfield, Wisconsin market. True Transport Inc.'s FMCSA score is strongest on unsafe-driving avoidance — 98th percentile.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
#3McLeod Express LLC — $1,483/wk
McLeod Express LLC debuts in the Greenfield, Wisconsin top 50 this month — it wasn't tracked here last month. McLeod Express LLC's top FMCSA dimension is unsafe-driving avoidance, in the 94th percentile. Weekly pay is guaranteed regardless of miles run.
If you want OTR routes without per-mile income variance, McLeod Express LLC is the only Greenfield, Wisconsin top-10 carrier pairing the two.
Also in the top 10: #4 PREMIER TRANSPORTATION at $1,950/wk, #5 SAFE WAY CARRIER LLC at $2,100/wk, #6 JK MOVING & STORAGE INC at $2,200/wk, #7 MNS1 EXPRESS INC at $2,050/wk, #8 HandledNow LLC at $1,550/wk, #9 Covenant Transport Inc at $1,762/wk, #10 Mountain States L.P. Gas at $2,000/wk.
What Greenfield, Wisconsin drivers actually run
21% of Greenfield, Wisconsin's active CDL postings are regional and 72% are OTR; local plus semi-local accounts for the rest (7%).
Across Greenfield, Wisconsin CDL postings: 3% with guaranteed pay, 25% dedicated, 78% take-truck-home, 64% pet-friendly, 64% riders-allowed.
How Greenfield, Wisconsin compares to Wisconsin
| Greenfield, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Dedicated routes | 32% | 41% | -9 pt |
| Pet-friendly fleets | 68% | 63% | +5 pt |
Source: Lanefinder index, November 2026
The largest gap is on dedicated routes: Greenfield, Wisconsin sits 9 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 Greenfield, Wisconsin
- CDL driver salary in Greenfield, 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.