Updated September 2026
Best Trucking Companies in Waukesha, Wisconsin (September 2026)
In Waukesha, Wisconsin as of September 2026, 363 carriers are actively hiring W2 company drivers. WESTERN MOUNTAIN TRANSPORT INC leads with an average weekly pay of $1,700 and an average $5,000 sign-on bonus. South East Carriers INC 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 September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Waukesha, Wisconsin's top trucking carriers right now
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 is number-one in Waukesha, Wisconsin this month on the composite ranking. WESTERN MOUNTAIN TRANSPORT INC's top FMCSA dimension is driver fitness, in the 93rd percentile. WESTERN MOUNTAIN TRANSPORT INC responds to driver applications more reliably than the Waukesha, Wisconsin median.
#2South East Carriers INC — $1,800/wk
South East Carriers INC's top FMCSA dimension is driver fitness, in the 93rd percentile. South East Carriers INC responds to driver applications more reliably than the Waukesha, Wisconsin median.
#3PREMIER TRANSPORTATION — $1,950/wk
PREMIER TRANSPORTATION pays above the 83rd percentile on weekly pay for the Waukesha, Wisconsin market. On driver fitness, the carrier ranks in the 98th percentile per FMCSA SAFER data.
Also in the top 10: #4 JK MOVING & STORAGE INC at $2,200/wk, #5 Covenant Transport Inc at $1,762/wk, #6 TDR TRANSPORT at $2,200/wk, #7 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #8 Badger Express LLC at $1,700/wk, #9 C & G TRANSPORTATION INC at $2,000/wk, #10 Diaz Stone & Pallet Inc. at $1,750/wk.
What Waukesha, Wisconsin drivers actually run
22% of Waukesha, Wisconsin's active CDL postings are regional and 71% are OTR; local plus semi-local accounts for the rest (7%).
Across Waukesha, Wisconsin CDL postings: 3% with guaranteed pay, 24% dedicated, 78% take-truck-home, 65% pet-friendly, 65% riders-allowed.
Waukesha, Wisconsin vs Wisconsin: the numbers that diverge
| Waukesha, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 50% | 37% | +13 pt |
| Pet-friendly fleets | 74% | 67% | +7 pt |
Source: Lanefinder index, September 2026
Among the figures above, sign-on bonus availability is where Waukesha, Wisconsin differs most from Wisconsin — 13 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 Waukesha, Wisconsin
- CDL driver salary in Waukesha, Wisconsin
- Best trucking companies in Wisconsin
Where this data comes from
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 September 2026.