Updated July 2026
Best Owner-Operator Companies in Chelsea, Massachusetts (July 2026)
492 carriers are hiring owner-operators in Chelsea, Massachusetts right now, per Lanefinder's July 2026 snapshot. 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.
The owner-operator carriers leading Chelsea, 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 Chelsea, Massachusetts ranking with the strongest composite score across pay, safety, benefits, and operational signals. ROLLING ON WHEELS LLC sits in the 93rd percentile for gross weekly revenue among Chelsea, Massachusetts carriers. ROLLING ON WHEELS LLC's FMCSA score is strongest on driver fitness — 96th percentile. ROLLING ON WHEELS LLC responds to driver applications more reliably than the Chelsea, Massachusetts median.
#2INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC sits in the 88th percentile for gross weekly revenue among Chelsea, Massachusetts carriers.
#3WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
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 Chelsea, Massachusetts drivers actually run
Of active CDL postings in Chelsea, Massachusetts this month, 8% are regional and 92% are OTR (long-haul). Local and semi-local routes account for the remaining 0%.
Guaranteed pay is on offer at 2% of Chelsea, Massachusetts postings; dedicated routes at 28%; take-truck-home at 93%. Pet-friendly policies appear at 73% and riders-allowed at 71%.
Chelsea, Massachusetts vs Massachusetts: the numbers that diverge
The largest gap is on average weekly pay: Chelsea, Massachusetts sits 12% 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 Chelsea, Massachusetts
- CDL driver salary in Chelsea, Massachusetts
- Best owner-operator companies in Massachusetts
How we compile these rankings
Composite-score formula: compensation × 0.30, FMCSA safety × 0.25, benefits × 0.25, operational performance × 0.20. Compensation is anchored on pay percentile and lifted by sign-on bonus tier and guaranteed-pay availability. Operational performance is built mostly from driver-application response data in Lanefinder's platform, with fleet-scale percentile contributing a smaller portion. Updated July 2026.