Updated July 2026
Best Owner-Operator Companies in Boston, Massachusetts (July 2026)
Lanefinder is tracking 492 owner-operator carriers in Boston, Massachusetts (July 2026). ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $8,500. INLAND EMPIRE LLC follows at $7,875/week gross. Boston freight runs on the I-90 / I-93 / I-95 metro grid, with the Port of Boston handling bulk and break-bulk cargo and a major biotech and pharmaceutical manufacturing cluster 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.
Boston, 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 Boston, Massachusetts this month on the composite ranking. Pay sits above the 88th percentile in the Boston, Massachusetts market. On driver fitness, the carrier ranks in the 96th percentile per FMCSA SAFER data. Lanefinder's application data flags ROLLING ON WHEELS LLC as a responsive employer.
#2INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC's gross weekly revenue ranks in the 88th percentile across Boston, Massachusetts.
#3WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. Driver applications get a faster-than-median response in Boston, Massachusetts.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 Rickman Transport, LLC at $9,250/wk, #6 OVERLOG INC at $3,613/wk, #7 Ali Star Inc at $9,000/wk, #8 BB8 FREIGHT CO at $12,666/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
Lane mix and benefits across Boston, Massachusetts
The route mix in Boston, 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 Boston, Massachusetts postings; dedicated routes at 28%; take-truck-home at 93%. Pet-friendly policies appear at 73% and riders-allowed at 71%.
Boston, Massachusetts vs Massachusetts: the numbers that diverge
The largest gap is on average weekly pay: Boston, Massachusetts sits 9% 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 Boston, Massachusetts
- CDL driver salary in Boston, Massachusetts
- Best owner-operator companies in Massachusetts
The methodology behind the rankings
Carriers are scored against carriers in their own market. The composite is 30% compensation (pay + bonus + guaranteed pay + settlement cadence), 25% FMCSA safety, 25% benefits (W2 vs owner-op scoring), and 20% operational performance (responsiveness + fleet scale). No paid placement — the weights are the same for every carrier in the index. Updated July 2026.