Updated July 2026
Best Owner-Operator Companies in Westfield, Massachusetts (July 2026)
506 owner-operator carriers are currently posting jobs in Westfield, Massachusetts as of July 2026. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $8,500. WINNERS TRANSPORTATION LLC follows at $2,437/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 Westfield, 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 Westfield, 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 Westfield, Massachusetts carriers. ROLLING ON WHEELS LLC's top FMCSA dimension is driver fitness, in the 96th percentile. Driver applications get a faster-than-median response in Westfield, Massachusetts.
#2WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Westfield, Massachusetts median.
#3INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC sits in the 88th percentile for gross weekly revenue among Westfield, Massachusetts carriers.
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 BLUE LIGHTNING LOGISTICS at $7,000/wk, #9 BB8 FREIGHT CO at $12,666/wk, #10 MEGA TRUCKS INC at $13,500/wk.
How drivers spend their time on the road in Westfield, Massachusetts
8% of Westfield, Massachusetts's active CDL postings are regional and 92% are OTR; local plus semi-local accounts for the rest (0%).
Guaranteed pay is on offer at 2% of Westfield, Massachusetts postings; dedicated routes at 28%; take-truck-home at 93%. Pet-friendly policies appear at 74% and riders-allowed at 71%.
Westfield, Massachusetts vs Massachusetts: the numbers that diverge
The largest gap is on average weekly pay: Westfield, Massachusetts sits 11% 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 Westfield, Massachusetts
- CDL driver salary in Westfield, Massachusetts
- Best owner-operator companies in Massachusetts
Where this data comes from
Four weighted components. Compensation carries 30% and includes pay percentile, sign-on bonus tier, guaranteed-pay availability, and settlement frequency. FMCSA safety carries 25%, built from five SAFER dimensions. Benefits carry 25%, scored separately for W2 versus owner-operator carriers. Operational performance carries 20%, measuring application responsiveness and fleet scale. Updated July 2026.