Updated July 2026
Best Owner-Operator Companies in Massachusetts (July 2026)
535 owner-operator carriers are hiring in Massachusetts this July 2026. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $5,500. 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.
Where owner-operator pay is strongest in Massachusetts this month
The top of the list is ROLLING ON WHEELS LLC at $5,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $5,500/wk
ROLLING ON WHEELS LLC leads the Massachusetts market on combined gross revenue and ranking score this month. ROLLING ON WHEELS LLC's top FMCSA dimension is driver fitness, in the 96th percentile. ROLLING ON WHEELS LLC responds to driver applications more reliably than the Massachusetts median.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
#3TITANIUM AMERICAN TRUCKING INC — $6,250/wk
TITANIUM AMERICAN TRUCKING INC's top FMCSA dimension is hours-of-service compliance, in the 97th percentile.
Also in the top 10: #4 OVERLOG INC at $3,613/wk, #5 WIDER GROUP INC at $6,250/wk, #6 Ali Star Inc at $10,000/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 TP TRUCKING at $8,500/wk.
Lane mix and benefits across Massachusetts
The route mix in Massachusetts this month tilts OTR: 8% regional, 92% OTR, 0% local, 0% semi-local — drawn from active postings, not historical surveys.
Guaranteed pay is on offer at 2% of Massachusetts postings; dedicated routes at 29%; take-truck-home at 92%. Pet-friendly policies appear at 73% and riders-allowed at 70%.
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 Massachusetts
- CDL driver salary in Massachusetts
- Best owner-operator 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 July 2026.