Updated September 2026
Best Owner-Operator Companies in Cambridge, Massachusetts (September 2026)
Cambridge, Massachusetts has 494 active owner-operator carriers as of September 2026. The carriers ranked below are scored on real driver pay, FMCSA safety, benefits, and how they treat applicants. RAY'S TRANSPORT INC leads with an average gross weekly revenue of $8,500 and an average $2,000 sign-on bonus. WINNERS TRANSPORTATION LLC follows at $2,657/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 September 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 Cambridge, Massachusetts this month
The top of the list is RAY'S TRANSPORT INC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1RAY'S TRANSPORT INC — $8,500/wk
RAY'S TRANSPORT INC tops the Cambridge, Massachusetts ranking with the strongest composite score across pay, safety, benefits, and operational signals. Pay sits above the 88th percentile in the Cambridge, Massachusetts market. RAY'S TRANSPORT INC's FMCSA score is strongest on driver fitness — 87th percentile. RAY'S TRANSPORT INC responds to driver applications more reliably than the Cambridge, Massachusetts median.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. WINNERS TRANSPORTATION LLC tracks as a responsive employer on application-response data.
#3TITANIUM AMERICAN TRUCKING INC — $6,250/wk
TITANIUM AMERICAN TRUCKING INC ranks in the 98th percentile for hours-of-service compliance on FMCSA SAFER data.
Also in the top 10: #4 Rickman Transport, LLC at $9,250/wk, #5 Ali Star Inc at $10,000/wk, #6 BLUE LIGHTNING LOGISTICS at $7,000/wk, #7 KILO METER LOGISTIC INC at $7,500/wk, #8 C & G TRANSPORTATION INC at $7,500/wk, #9 LOAD MONSTER INC at $2,450/wk, #10 MEGA TRUCKS INC at $13,500/wk.
What Cambridge, Massachusetts drivers actually run
Of active CDL postings in Cambridge, Massachusetts this month, 8% are regional and 92% are OTR (long-haul). Local and semi-local routes account for the remaining 0%.
Across Cambridge, Massachusetts CDL postings: 2% with guaranteed pay, 28% dedicated, 93% take-truck-home, 73% pet-friendly, 70% riders-allowed.
How Cambridge, Massachusetts compares to Massachusetts
The largest gap is on average weekly pay: Cambridge, Massachusetts sits 5% 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 Cambridge, Massachusetts
- CDL driver salary in Cambridge, 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 September 2026.