Updated May 2026
Best Trucking Companies in Greenfield, Wisconsin (May 2026)
Through May 2026, 370 carriers in Greenfield, Wisconsin employ W2 company drivers across the lanes Lanefinder tracks. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. 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 May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Where CDL pay is strongest in Greenfield, Wisconsin this month
The top of the list is KEEP TRUCKING LLC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1KEEP TRUCKING LLC — $2,200/wk
KEEP TRUCKING LLC leads the Greenfield, Wisconsin market on combined pay and ranking score this month. KEEP TRUCKING LLC sits in the 95th percentile for weekly pay among Greenfield, Wisconsin carriers. KEEP TRUCKING LLC's FMCSA score is strongest on controlled-substances compliance — 88th percentile. KEEP TRUCKING LLC responds to driver applications more reliably than the Greenfield, Wisconsin median.
#2True Transport Inc. — $2,250/wk
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 — 99th percentile. Driver applications get a faster-than-median response in Greenfield, Wisconsin.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC sits in the 95th percentile for weekly pay among Greenfield, Wisconsin carriers. Top FMCSA dimension here is unsafe-driving avoidance, in the 94th percentile.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #6 PREMIER TRANSPORTATION at $1,700/wk, #7 KEN GRAHAM TRUCKING INC at $2,000/wk, #8 Badger Express LLC at $1,700/wk, #9 JS HELWIG & SON LLC at $1,850/wk, #10 Diaz Stone & Pallet Inc. at $1,750/wk.
What Greenfield, Wisconsin drivers actually run
20% of Greenfield, Wisconsin's active CDL postings are regional and 73% are OTR; local plus semi-local accounts for the rest (7%).
Across Greenfield, Wisconsin CDL postings: 1% with guaranteed pay, 24% dedicated, 79% take-truck-home, 64% pet-friendly, 65% riders-allowed.
How Greenfield, Wisconsin compares to Wisconsin
| Greenfield, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 48% | 38% | +10 pt |
| Pet-friendly fleets | 72% | 67% | +5 pt |
Source: Lanefinder index, May 2026
The largest gap is on sign-on bonus availability: Greenfield, Wisconsin sits 10 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 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 May 2026.