Updated November 2026
Best Owner-Operator Companies in Pittsfield, Massachusetts (November 2026)
Pittsfield, Massachusetts has 508 active owner-operator carriers as of November 2026. The carriers ranked below are scored on real driver pay, FMCSA safety, benefits, and how they treat applicants. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $8,500. MONDO MOTION LLC follows at $9,250/week gross. Massachusetts freight runs on the I-90 / I-93 / I-95 metro grid through Boston, with Port of Boston handling bulk and container cargo and the nation's largest life-sciences cluster generating cold-chain and hazmat lanes.
What changed in November 2026
ROLLING ON WHEELS LLC at #1, MONDO MOTION LLC at #2, and MAYBACH INTERNATIONAL GROUP INC at #3 are new to the top 50 in Pittsfield, Massachusetts. Biggest climb: WLC GROUP INC (#30 → #20). RAY'S TRANSPORT INC (was #1) and KILO METER LOGISTIC INC (was #7) left the top 50. Average weekly pay moved most at EXPRESS CR INC (up 18.2% from $2,750 to $3,250). Elsewhere in the top 50, 4 carriers joined, 5 left, and 31 changed rank.
All changes since October 2026
| Carrier | Last month | This month | Change |
|---|---|---|---|
| ROLLING ON WHEELS LLC | Not ranked | #1 | New |
| MONDO MOTION LLC | Not ranked | #2 | New |
| MAYBACH INTERNATIONAL GROUP INC | Not ranked | #3 | New |
| Rickman Transport, LLC | #2 | #4 | Down 2 places |
| WINNERS TRANSPORTATION LLC | Not ranked | #5 | New |
| BLUE LIGHTNING LOGISTICS | #3 | #7 | Down 4 places |
| Ali Star Inc | #4 | #8 | Down 4 places |
| C & G TRANSPORTATION INC | #5 | #9 | Down 4 places |
| MEGA TRUCKS INC | #8 | #10 | Down 2 places |
| M&D TRANSPORT | #10 | #11 | Down 1 place |
| TITAN FREIGHT LINES INC | #9 | #12 | Down 3 places |
| Goldway Trans LLC | #11 | #13 | Down 2 places |
| JK MOVING & STORAGE INC | #12 | #14 | Down 2 places |
| HERMES NVC CORP | Not ranked | #15 | New |
| ITF Group | #14 | #16 | Down 2 places |
| LUXOR DRIVE INC | #13 | #17 | Down 4 places |
| FIVE STAR TRUCKING INC | #15 | #18 | Down 3 places |
| TIM RYAN TRUCKING LLC | #17 | #19 | Down 2 places |
| WLC GROUP INC | #30 | #20 | Up 10 placesweekly pay up 4.2% ($3,000 → $3,125) |
| CO Lines Inc | #19 | #21 | Down 2 places |
| BIG JOHN EXPEDITED INC | #16 | #22 | Down 6 places |
| LEGACY CARGO LLC | #22 | #24 | Down 2 places |
| J & J Oil LLC | #18 | #25 | Down 7 places |
| STEPANOV TRUCKING LLC | #28 | #26 | Up 2 places |
| EXPRESS CR INC | #32 | #28 | Up 4 placesweekly pay up 18.2% ($2,750 → $3,250) |
| AS TRANSPORTATION INC | Not ranked | #30 | New |
| D & H CATTLE COMPANY LLC | #33 | #31 | Up 2 places |
| American Eagle Enterprise | #34 | #32 | Up 2 places |
| COMMONWEALTH TRANSPORTATION LLC | #35 | #33 | Up 2 places |
| A & H INC | #37 | #34 | Up 3 places |
| LINESTAR EXPRESS LLC | #31 | #35 | Down 4 places |
| LEADER FREIGHT SYSTEMS | #38 | #37 | Up 1 place |
| STAR PARTNERS LLC | Not ranked | #38 | New |
| MILESTONE TRUCKING LLC | #43 | #42 | Up 1 place |
| HORIZON TRANSPORTATION | #42 | #43 | Down 1 place |
| VITAL TRANSPORTATION CORP | #45 | #44 | Up 1 place |
| BREEZE TRANSPORTATION INCORPORATED | #46 | #45 | Up 1 place |
| STRAIGHT LOGISTICS INC | #44 | #46 | Down 2 places |
| REAL TRUCKING INC | #48 | #47 | Up 1 place |
| REVEL TRANSPORT LLC | #47 | #48 | Down 1 place |
| RAY'S TRANSPORT INC | #1 | Not ranked | Dropped out |
| KILO METER LOGISTIC INC | #7 | Not ranked | Dropped out |
| A&M CARRIERS INC | #20 | Not ranked | Dropped out |
| AIA TRUCKING INC | #21 | Not ranked | Dropped out |
| BLACK EAGLE EXPRESS LLC | #24 | Not ranked | Dropped out |
| DOGE Trucking LLC | #25 | Not ranked | Dropped out |
| MAX MOVE LLC | #26 | Not ranked | Dropped out |
Pittsfield, Massachusetts's top owner-operator carriers right now
The top of the list is ROLLING ON WHEELS LLC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $8,500/wk
ROLLING ON WHEELS LLC is number-one in Pittsfield, Massachusetts this month on the composite ranking. ROLLING ON WHEELS LLC's gross weekly revenue ranks in the 93rd percentile across Pittsfield, Massachusetts. Strongest FMCSA dimension is driver fitness — 87th percentile. ROLLING ON WHEELS LLC tracks as a responsive employer on application-response data.
#2MONDO MOTION LLC — $9,250/wk
MONDO MOTION LLC makes its first-time appearance in Pittsfield, Massachusetts's ranking this month. The carrier ranks in the 95th percentile for gross weekly revenue in Pittsfield, Massachusetts. Strongest FMCSA dimension is hours-of-service compliance — 98th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#3MAYBACH INTERNATIONAL GROUP INC — $3,025/wk
MAYBACH INTERNATIONAL GROUP INC makes its first-time appearance in Pittsfield, Massachusetts's ranking this month. MAYBACH INTERNATIONAL GROUP INC's FMCSA score is strongest on driver fitness — 96th percentile. Lanefinder's application data flags MAYBACH INTERNATIONAL GROUP INC as a responsive employer.
Also in the top 10: #4 Rickman Transport, LLC at $9,250/wk, #5 WINNERS TRANSPORTATION LLC at $2,657/wk, #6 IKKO LOGISTICS LLC at $7,500/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 Ali Star Inc at $10,000/wk, #9 C & G TRANSPORTATION INC at $7,500/wk, #10 MEGA TRUCKS INC at $13,500/wk.
How drivers spend their time on the road in Pittsfield, Massachusetts
The route mix in Pittsfield, Massachusetts this month tilts OTR: 8% regional, 92% OTR, 0% local, 0% semi-local — drawn from active postings, not historical surveys.
Across Pittsfield, Massachusetts CDL postings: 1% with guaranteed pay, 29% dedicated, 93% take-truck-home, 72% pet-friendly, 70% riders-allowed.
How Pittsfield, Massachusetts compares to Massachusetts
The largest gap is on average weekly pay: Pittsfield, Massachusetts sits 7% above the Massachusetts baseline.
Driving CDL in Massachusetts
Massachusetts freight runs on the I-90 / I-93 / I-95 grid through Boston, with the Port of Boston handling bulk and container cargo. A dense biotech and pharmaceutical manufacturing cluster around Cambridge / Boston / Worcester requires cold-chain and hazmat-eligible lanes. The Big Dig tunnels have truck-height and hazmat restrictions worth checking before routing. Boston congestion is a recurring truck bottleneck. Cost of living is among the highest nationally. Massachusetts has a moderate flat state income tax with an added surtax on very high incomes (not relevant for most drivers).
Related guides
- Best trucking companies in Pittsfield, Massachusetts
- CDL driver salary in Pittsfield, Massachusetts
- Best owner-operator companies in Massachusetts
How we compile these rankings
Lanefinder's ranking algorithm weights compensation at 30%, FMCSA SAFER safety at 25%, benefits at 25%, and operational performance at 20%. Compensation reflects pay percentile plus sign-on bonus, guaranteed pay, and settlement-frequency adjustments. Benefits scoring is hiring-type-aware. Operational performance comes mostly from how carriers handle real driver applications. Updated November 2026.