Updated November 2026
Best Trucking Companies in Wisconsin (November 2026)
For W2 company drivers in Wisconsin, Lanefinder tracks 615 carriers as of November 2026. Herrington Transportation Inc. leads with an average weekly pay of $2,000. FW TRUCKING 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 #3 is new to the top 50 in Wisconsin. Biggest climbs: Herrington Transportation Inc. (#39 → #1), FW TRUCKING (#24 → #2), and True Transport Inc. (#20 → #8). Biggest falls: LAWRENCE TRANSPORTATION COMPANY (#1 → #25), SECOR LOGISTICS LLC (#12 → #23), and C & G TRANSPORTATION INC (#19 → #29). Elsewhere in the top 50, 7 carriers joined, 8 left, and 33 changed rank.
All changes since October 2026
Wisconsin's top trucking carriers right now
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. leads the Wisconsin market on combined pay and ranking score this month. Herrington Transportation Inc. sits in the 93rd percentile for weekly pay among Wisconsin carriers. Herrington Transportation Inc. responds to driver applications more reliably than the Wisconsin median.
#2FW TRUCKING — $1,800/wk
FW TRUCKING climbed from #24 to #2 this month — one of the biggest moves in Wisconsin. FW TRUCKING's weekly pay ranks in the 85th percentile across Wisconsin. FW TRUCKING ranks in the 90th percentile for unsafe-driving avoidance on FMCSA SAFER data.
#3McLeod Express LLC — $1,462/wk
McLeod Express LLC debuts in the Wisconsin top 50 this month — it wasn't tracked here last month. Top FMCSA dimension here is unsafe-driving avoidance, in the 94th percentile. McLeod Express LLC runs a guaranteed-pay structure on the comp package.
Long-haul drivers who want a guaranteed paycheck: McLeod Express LLC is the only Wisconsin top-10 carrier offering it on OTR runs.
Also in the top 10: #4 HAZMAT ENVIRONMENTAL GROUP INC at $2,100/wk, #5 HandledNow LLC at $1,550/wk, #6 South East Carriers INC at $1,700/wk, #7 PREMIER TRANSPORTATION at $1,950/wk, #8 True Transport Inc. at $2,250/wk, #9 Covenant Transport Inc at $1,762/wk, #10 JK MOVING & STORAGE INC at $2,200/wk.
What Wisconsin drivers actually run
The route mix in Wisconsin this month tilts OTR: 25% regional, 56% OTR, 16% local, 3% semi-local — drawn from active postings, not historical surveys.
Guaranteed pay is on offer at 2% of Wisconsin postings; dedicated routes at 28%; take-truck-home at 67%. Pet-friendly policies appear at 54% and riders-allowed at 56%.
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 Wisconsin
- CDL driver salary in Wisconsin
- Best trucking companies in the United States
Where this data comes from
Compensation (30%): pay percentile + sign-on bonus + guaranteed pay + settlement frequency. FMCSA safety (25%): weighted percentile across vehicle maintenance, unsafe driving, hours-of-service, driver fitness, and controlled substances. Benefits (25%): hiring-type-aware. Operational (20%): driver-application responsiveness, modulated by fleet scale. Updated November 2026.