Updated September 2026
Best Trucking Companies in Greenfield, Wisconsin (September 2026)
Through September 2026, 363 carriers in Greenfield, Wisconsin employ W2 company drivers across the lanes Lanefinder tracks. WESTERN MOUNTAIN TRANSPORT INC leads with an average weekly pay of $1,700 and an average $5,000 sign-on bonus. PREMIER TRANSPORTATION follows at $1,950/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 September 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 WESTERN MOUNTAIN TRANSPORT INC at $1,700/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1WESTERN MOUNTAIN TRANSPORT INC — $1,700/wk
WESTERN MOUNTAIN TRANSPORT INC tops the Greenfield, Wisconsin ranking with the strongest composite score across pay, safety, benefits, and operational signals. WESTERN MOUNTAIN TRANSPORT INC's top FMCSA dimension is driver fitness, in the 93rd percentile. Driver applications get a faster-than-median response in Greenfield, Wisconsin.
#2PREMIER TRANSPORTATION — $1,950/wk
PREMIER TRANSPORTATION's weekly pay ranks in the 88th percentile across Greenfield, Wisconsin. PREMIER TRANSPORTATION's top FMCSA dimension is driver fitness, in the 98th percentile.
#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 93rd percentile.
Despite ranking below #1, JK MOVING & STORAGE INC outpays the leader on weekly average — $2,200/week.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 TDR TRANSPORT at $2,200/wk, #6 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #7 Badger Express LLC at $1,700/wk, #8 C & G TRANSPORTATION INC at $2,000/wk, #9 Diaz Stone & Pallet Inc. at $1,750/wk, #10 JS HELWIG & SON LLC at $1,850/wk.
What Greenfield, Wisconsin drivers actually run
22% of Greenfield, Wisconsin's active CDL postings are regional and 71% are OTR; local plus semi-local accounts for the rest (7%).
Across Greenfield, Wisconsin CDL postings: 3% with guaranteed pay, 24% dedicated, 78% take-truck-home, 65% pet-friendly, 65% riders-allowed.
How Greenfield, Wisconsin compares to Wisconsin
| Greenfield, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 48% | 37% | +11 pt |
| Pet-friendly fleets | 74% | 67% | +7 pt |
Source: Lanefinder index, September 2026
The largest gap is on sign-on bonus availability: Greenfield, Wisconsin sits 11 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 September 2026.