Updated July 2026
Best Owner-Operator Companies in Cambridge, Massachusetts (July 2026)
Cambridge, Massachusetts has 492 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. INLAND EMPIRE LLC follows at $7,875/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 Cambridge, Massachusetts this month
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 tops the Cambridge, Massachusetts ranking with the strongest composite score across pay, safety, benefits, and operational signals. The carrier ranks in the 93rd percentile for gross weekly revenue in Cambridge, Massachusetts. ROLLING ON WHEELS LLC ranks in the 96th percentile for driver fitness on FMCSA SAFER data. ROLLING ON WHEELS LLC tracks as a responsive employer on application-response data.
#2INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC pays above the 83rd percentile on gross weekly revenue for the Cambridge, Massachusetts market.
#3WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. WINNERS TRANSPORTATION LLC tracks as a responsive employer on application-response data.
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.
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, 71% riders-allowed.
How Cambridge, Massachusetts compares to Massachusetts
The largest gap is on average weekly pay: Cambridge, Massachusetts sits 10% 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 July 2026.