Updated May 2026
Best Trucking Companies in Madison, Wisconsin (May 2026)
352 carriers are hiring W2 company drivers in Madison, Wisconsin right now, per Lanefinder's May 2026 snapshot. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. Madison sits at the I-90 / I-94 junction in south-central Wisconsin, with large-scale dairy and food processing, university institutional procurement, and manufacturing distribution for the Wisconsin River Valley corridor.
What changed in May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Madison, Wisconsin's top trucking carriers right now
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 is number-one in Madison, Wisconsin this month on the composite ranking. KEEP TRUCKING LLC pays above the 90th percentile on weekly pay for the Madison, Wisconsin market. On controlled-substances compliance, the carrier ranks in the 88th percentile per FMCSA SAFER data. KEEP TRUCKING LLC responds to driver applications more reliably than the Madison, Wisconsin median.
#2True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 97th percentile for weekly pay among Madison, Wisconsin carriers. True Transport Inc.'s top FMCSA dimension is unsafe-driving avoidance, in the 99th percentile. Lanefinder's application data flags True Transport Inc. as a responsive employer.
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 pays above the 90th percentile on weekly pay for the Madison, Wisconsin market. Strongest FMCSA dimension is unsafe-driving avoidance — 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 KOTTKE TRUCKING INC at $2,000/wk, #9 Badger Express LLC at $1,700/wk, #10 JS HELWIG & SON LLC at $1,850/wk.
What Madison, Wisconsin drivers actually run
The route mix in Madison, Wisconsin this month tilts OTR: 20% regional, 76% OTR, 3% local, 1% semi-local — drawn from active postings, not historical surveys.
Across Madison, Wisconsin CDL postings: 1% with guaranteed pay, 24% dedicated, 80% take-truck-home, 67% pet-friendly, 67% riders-allowed.
How Madison, Wisconsin compares to Wisconsin
| Madison, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 48% | 38% | +10 pt |
| Pet-friendly fleets | 74% | 67% | +7 pt |
| Riders-allowed policies | 80% | 73% | +7 pt |
Source: Lanefinder index, May 2026
Among the figures above, sign-on bonus availability is where Madison, Wisconsin differs most from Wisconsin — 10 points above 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 Madison, Wisconsin
- CDL driver salary in Madison, Wisconsin
- Best trucking companies in Wisconsin
The methodology behind the rankings
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 May 2026.