Updated May 2026
Best Trucking Companies in Massachusetts (May 2026)
For W2 company drivers in Massachusetts, Lanefinder tracks 321 carriers as of May 2026. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. 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 May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
The trucking companies leading Massachusetts this month
The top of the list is KEEP TRUCKING LLC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1KEEP TRUCKING LLC — $2,200/wk
KEEP TRUCKING LLC tops the Massachusetts ranking with the strongest composite score across pay, safety, benefits, and operational signals. Pay sits above the 90th percentile in the Massachusetts market. KEEP TRUCKING LLC's FMCSA score is strongest on controlled-substances compliance — 88th percentile. Lanefinder's application data flags KEEP TRUCKING LLC as a responsive employer.
#2True Transport Inc. — $2,250/wk
True Transport Inc. pays above the 92nd percentile on weekly pay for the Massachusetts market. On unsafe-driving avoidance, the carrier ranks in the 99th percentile per FMCSA SAFER data. Driver applications get a faster-than-median response in Massachusetts.
True Transport Inc. actually pays more weekly than the top-ranked carrier — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC's weekly pay ranks in the 95th percentile across Massachusetts. Top FMCSA dimension here is unsafe-driving avoidance, in the 94th percentile.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 HMD TRUCKING INC at $1,800/wk, #6 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #7 DIVINE ENTERPRISES at $1,375/wk, #8 GATEWAY DISTRIBUTION at $1,750/wk, #9 ABENAQUI CARRIERS at $1,750/wk, #10 PREMIER TRANSPORTATION at $1,700/wk.
What Massachusetts drivers actually run
20% of Massachusetts's active CDL postings are regional and 62% are OTR; local plus semi-local accounts for the rest (18%).
Across Massachusetts CDL postings: 2% with guaranteed pay, 27% dedicated, 65% take-truck-home, 53% pet-friendly, 54% riders-allowed.
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 owner-operator companies in Massachusetts
- CDL driver salary in Massachusetts
- Best trucking companies in the United States
How we compile these rankings
Compensation is the largest single weight at 30% — pay percentile, sign-on bonus, guaranteed-pay availability, and settlement cadence. FMCSA safety contributes 25%, built from five SAFER dimensions with unsafe-driving and hours-of-service weighted 2× heavier. Benefits contribute 25%, scored separately for W2 versus owner-operator and 1099 carriers. Operational performance — application responsiveness and fleet scale — contributes 20%. Updated May 2026.