Updated November 2026
Best Trucking Companies in Madison, Wisconsin (November 2026)
347 carriers are hiring W2 company drivers in Madison, Wisconsin right now, per Lanefinder's November 2026 snapshot. Herrington Transportation Inc. leads with an average weekly pay of $2,000. South East Carriers INC follows at $1,800/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 I-90 / I-94 corridor.
What changed in November 2026
SAFE WAY CARRIER LLC at #5, MNS1 EXPRESS INC at #7, and Mountain States L.P. Gas at #9 are new to the top 50 in Madison, Wisconsin. Biggest climbs: Herrington Transportation Inc. (#34 → #1) and TAYLOR TRUCK LINE INC (#33 → #21). Biggest falls: LAWRENCE TRANSPORTATION COMPANY (#2 → #23) and K-WAY EXPRESS INC (#24 → #34). Average weekly pay moved most at TAYLOR TRUCK LINE INC (up 9.5% from $1,525 to $1,670). Elsewhere in the top 50, 4 carriers joined, 7 left, and 37 changed rank.
All changes since October 2026
| Carrier | Last month | This month | Change |
|---|---|---|---|
| Herrington Transportation Inc. | #34 | #1 | Up 33 places |
| South East Carriers INC | #1 | #2 | Down 1 place |
| True Transport Inc. | #10 | #3 | Up 7 places |
| PREMIER TRANSPORTATION | #3 | #4 | Down 1 place |
| SAFE WAY CARRIER LLC | Not ranked | #5 | New |
| JK MOVING & STORAGE INC | #4 | #6 | Down 2 places |
| MNS1 EXPRESS INC | Not ranked | #7 | New |
| Covenant Transport Inc | #5 | #8 | Down 3 places |
| Mountain States L.P. Gas | Not ranked | #9 | New |
| McLeod Express LLC | Not ranked | #10 | New |
| PRAIRIE FIELD SERVICES LLC | #6 | #11 | Down 5 places |
| ARKA EXPRESS INC | Not ranked | #12 | New |
| Badger Express LLC | #7 | #13 | Down 6 places |
| JS HELWIG & SON LLC | #9 | #14 | Down 5 places |
| Diaz Stone & Pallet Inc. | #8 | #15 | Down 7 places |
| G-DIAMOND TRANSPORT INC | #11 | #16 | Down 5 places |
| ZELLER TRANSPORTATION LLC | #14 | #17 | Down 3 places |
| ALBA TRANS INC | #13 | #18 | Down 5 places |
| ELBERTA LOGISTICS INTERNATIONAL LLC | #15 | #19 | Down 4 places |
| CYCLE LOGISTICS INC | #12 | #20 | Down 8 places |
| TAYLOR TRUCK LINE INC | #33 | #21 | Up 12 placesweekly pay up 9.5% ($1,525 → $1,670) |
| MC CARRIER LLC | #18 | #22 | Down 4 places |
| LAWRENCE TRANSPORTATION COMPANY | #2 | #23 | Down 21 places |
| BRADY TRUCKING INC | #16 | #24 | Down 8 places |
| KEN GRAHAM TRUCKING INC | #19 | #25 | Down 6 places |
| A & H INC | #29 | #26 | Up 3 places |
| HOLLAND ENTERPRISES INC | #25 | #27 | Down 2 places |
| KAISER TRANSPORT INC | #22 | #28 | Down 6 places |
| NEIER INC | #21 | #29 | Down 8 places |
| AFC Transport, Inc | #28 | #30 | Down 2 places |
| RIVER CITY TRANSPORT INC | #23 | #31 | Down 8 places |
| PASCAL CARRIER INC | #27 | #32 | Down 5 places |
| HAWKS TRANSPORT LLC | Not ranked | #33 | New |
| K-WAY EXPRESS INC | #24 | #34 | Down 10 places |
| AN ENTERPRISE INC | #31 | #36 | Down 5 places |
| Excel Trucking LLC | #32 | #37 | Down 5 places |
| LUCKY WORLD INC | Not ranked | #38 | New |
| BARTELS TRUCK LINE INC | #36 | #39 | Down 3 places |
| Bertch Cabinet LLC | #37 | #40 | Down 3 places |
| CARGORX DRY CAPACITY | #38 | #41 | Down 3 places |
| GURTLER INDUSTRIES INC | #39 | #42 | Down 3 places |
| HUTCHINSON TRUCKING LLC | #40 | #43 | Down 3 places |
| TDR TRANSPORT | #43 | #44 | Down 1 place |
| CTK LOGISTICS LLC | #46 | #45 | Up 1 place |
| Bakers Express | #47 | #46 | Up 1 place |
| EAGLE EYE TRUCK LINES LLC | #48 | #47 | Up 1 place |
| S & R TRANSPORTATION LLC | #50 | #48 | Up 2 places |
| REISCH TRUCKING INC | #41 | #50 | Down 9 places |
| H & M TRUCKING INC | #17 | Not ranked | Dropped out |
| WILLIAMS PRESTIGE ENTERPRISE | #20 | Not ranked | Dropped out |
| UPPER LAKES FOODS INC | #26 | Not ranked | Dropped out |
| M&D TRANSPORT | #30 | Not ranked | Dropped out |
| GT WORLDWIDE TRANSPORT INC | #42 | Not ranked | Dropped out |
| MAJOR TRANSPORTATION SERVICES LLC | #44 | Not ranked | Dropped out |
| JL LOGISTICS INC | #45 | Not ranked | Dropped out |
Madison, 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 Madison, Wisconsin market on combined pay and ranking score this month. Herrington Transportation Inc.'s weekly pay ranks in the 91st percentile across Madison, Wisconsin. Application-response data flags this carrier as a responsive employer.
#2South East Carriers INC — $1,800/wk
South East Carriers INC's FMCSA score is strongest on controlled-substances compliance — 96th percentile. Lanefinder's application data flags South East Carriers INC as a responsive employer.
#3True Transport Inc. — $2,250/wk
True Transport Inc. rose 7 positions month-over-month, from #10 to #3. 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 98th percentile.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
Also in the top 10: #4 PREMIER TRANSPORTATION at $1,950/wk, #5 SAFE WAY CARRIER LLC at $2,100/wk, #6 JK MOVING & STORAGE INC at $2,200/wk, #7 MNS1 EXPRESS INC at $2,050/wk, #8 Covenant Transport Inc at $1,762/wk, #9 Mountain States L.P. Gas at $2,000/wk, #10 McLeod Express LLC at $1,400/wk.
What Madison, Wisconsin drivers actually run
The route mix in Madison, Wisconsin this month tilts OTR: 20% regional, 75% OTR, 4% local, 1% semi-local — drawn from active postings, not historical surveys.
Across Madison, Wisconsin CDL postings: 2% with guaranteed pay, 26% dedicated, 80% take-truck-home, 66% pet-friendly, 67% riders-allowed.
How Madison, Wisconsin compares to Wisconsin
| Madison, Wisconsin | Wisconsin top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 40% | 35% | +5 pt |
| Dedicated routes | 32% | 41% | -9 pt |
| Pet-friendly fleets | 72% | 63% | +9 pt |
| Riders-allowed policies | 80% | 71% | +9 pt |
Source: Lanefinder index, November 2026
Among the figures above, dedicated routes is where Madison, Wisconsin differs most from Wisconsin — 9 points below statewide.
Driving CDL in Madison
Madison anchors south-central Wisconsin at the I-90 / I-94 / I-39 cross. State government supply chains, University of Wisconsin distribution, and biotech / pharma freight carry most of the dispatch volume. Cost of living is below the national average. Winter is severe; lake-effect snow doesn't reach here but ice and sub-zero stretches do.
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 November 2026.