Updated July 2026
Best Owner-Operator Companies in Pittsfield, Massachusetts (July 2026)
Pittsfield, Massachusetts has 506 active owner-operator carriers as of July 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. WINNERS TRANSPORTATION LLC follows at $2,437/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 a major concentration of biotech and pharmaceutical manufacturing requiring cold-chain and hazmat lanes.
What changed in July 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
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 — 96th percentile. ROLLING ON WHEELS LLC tracks as a responsive employer on application-response data.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. WINNERS TRANSPORTATION LLC tracks as a responsive employer on application-response data.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC's gross weekly revenue ranks in the 88th percentile across Pittsfield, Massachusetts.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 OVERLOG INC at $3,613/wk, #6 Ali Star Inc at $9,000/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 BB8 FREIGHT CO at $12,666/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: 2% with guaranteed pay, 28% dedicated, 93% take-truck-home, 74% pet-friendly, 71% riders-allowed.
How Pittsfield, Massachusetts compares to Massachusetts
The largest gap is on average weekly pay: Pittsfield, Massachusetts sits 12% 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 consistently in the worst US tier. 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 July 2026.