Updated May 2026
Best Trucking Companies in Boston, Massachusetts (May 2026)
239 carriers are hiring W2 company drivers in Boston, Massachusetts right now, per Lanefinder's May 2026 snapshot. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. Boston freight runs on the I-90 / I-93 / I-95 metro grid, with the Port of Boston handling bulk and break-bulk cargo and a major biotech and pharmaceutical manufacturing cluster 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.
Boston, Massachusetts's top trucking carriers right now
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 Boston, Massachusetts ranking with the strongest composite score across pay, safety, benefits, and operational signals. KEEP TRUCKING LLC pays above the 89th percentile on weekly pay for the Boston, Massachusetts market. KEEP TRUCKING LLC's top FMCSA dimension is controlled-substances compliance, in the 88th percentile. KEEP TRUCKING LLC responds to driver applications more reliably than the Boston, Massachusetts median.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 97th percentile across Boston, Massachusetts. True Transport Inc.'s FMCSA score is strongest on unsafe-driving avoidance — 99th percentile. Lanefinder's application data flags True Transport Inc. as a responsive employer.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC pays above the 89th percentile on weekly pay for the Boston, Massachusetts market. JK MOVING & STORAGE INC ranks in the 94th percentile for unsafe-driving avoidance on FMCSA SAFER data.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 HMD TRUCKING INC at $1,875/wk, #6 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #7 DIVINE ENTERPRISES at $1,375/wk, #8 JS HELWIG & SON LLC at $1,850/wk, #9 PREMIER TRANSPORTATION at $1,700/wk, #10 ABENAQUI CARRIERS at $1,750/wk.
Lane mix and benefits across Boston, Massachusetts
17% of Boston, Massachusetts's active CDL postings are regional and 75% are OTR; local plus semi-local accounts for the rest (8%).
Across Boston, Massachusetts CDL postings: 1% with guaranteed pay, 27% dedicated, 71% take-truck-home, 61% pet-friendly, 60% 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 Boston, Massachusetts
- CDL driver salary in Boston, Massachusetts
- Best trucking companies in Massachusetts
Where this data comes from
The score is built from four buckets. Thirty percent compensation, drawn from real active job postings and modified by bonus and settlement structure. Twenty-five percent safety, from FMCSA SAFER. Twenty-five percent benefits, scored hiring-type-aware. Twenty percent operational performance, drawn from how carriers actually behave toward applicants. Updated May 2026.