Updated May 2026
Best Owner-Operator Companies in Massachusetts (May 2026)
534 owner-operator carriers are hiring in Massachusetts this May 2026. YANKEE FREIGHT SYSTEMS LLC leads with an average gross weekly revenue of $5,491 and an average $2,000 sign-on bonus. Zmile Inc follows at $2,987/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 May 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 YANKEE FREIGHT SYSTEMS LLC at $5,491/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1YANKEE FREIGHT SYSTEMS LLC — $5,491/wk
YANKEE FREIGHT SYSTEMS LLC leads the Massachusetts market on combined gross revenue and ranking score this month. Strongest FMCSA dimension is hours-of-service compliance — 98th percentile. Application-response data flags this carrier as a responsive employer.
#2Zmile Inc — $2,987/wk
Zmile Inc's FMCSA score is strongest on hours-of-service compliance — 98th percentile. Driver applications get a faster-than-median response in Massachusetts.
#3AD EXPRESS TRUCKING LLC — $2,416/wk
AD EXPRESS TRUCKING LLC responds to driver applications more reliably than the Massachusetts median. AD EXPRESS TRUCKING LLC runs a guaranteed-pay structure on the comp package.
For guaranteed weekly pay, AD EXPRESS TRUCKING LLC is the only top-10 Massachusetts carrier offering it.
Also in the top 10: #4 WIDER GROUP INC at $6,250/wk, #5 D-LINE TRUCKING INC at $5,750/wk, #6 INLAND EMPIRE LLC at $7,875/wk, #7 Rickman Transport, LLC at $9,250/wk, #8 Ali Star Inc at $10,000/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 TITAN FREIGHT LINES INC at $8,500/wk.
Lane mix and benefits across Massachusetts
The route mix in Massachusetts this month tilts OTR: 8% regional, 91% OTR, 0% local, 2% semi-local — drawn from active postings, not historical surveys.
Guaranteed pay is on offer at 1% of Massachusetts postings; dedicated routes at 28%; 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 May 2026.