Updated September 2026
Best Owner-Operator Companies in Chelsea, Massachusetts (September 2026)
494 carriers are hiring owner-operators in Chelsea, Massachusetts right now, per Lanefinder's September 2026 snapshot. 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.
The owner-operator carriers leading Chelsea, 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 Chelsea, 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 Chelsea, Massachusetts. Top FMCSA dimension here is driver fitness, in the 87th percentile. Application-response data flags this carrier as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
#3TITANIUM AMERICAN TRUCKING INC — $6,250/wk
TITANIUM AMERICAN TRUCKING INC's FMCSA score is strongest on hours-of-service compliance — 98th percentile.
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 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 70%.
Chelsea, Massachusetts vs Massachusetts: the numbers that diverge
The largest gap is on average weekly pay: Chelsea, 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 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 September 2026.