Updated May 2026
Best Trucking Companies in Pittsfield, Massachusetts (May 2026)
Pittsfield, Massachusetts, May 2026: 237 active W2 trucking carriers. 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.
Pittsfield, 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 is number-one in Pittsfield, Massachusetts this month on the composite ranking. The carrier ranks in the 94th percentile for weekly pay in Pittsfield, Massachusetts. Strongest FMCSA dimension is controlled-substances compliance — 88th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#2True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 96th percentile for weekly pay among Pittsfield, Massachusetts carriers. Strongest FMCSA dimension is unsafe-driving avoidance — 99th percentile. True Transport Inc. tracks as a responsive employer on application-response data.
For pure pay maximization, True Transport Inc. beats the #1-ranked carrier weekly at $2,250.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC pays above the 89th percentile on weekly pay for the Pittsfield, Massachusetts market. JK MOVING & STORAGE INC's top FMCSA dimension 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 JS HELWIG & SON LLC at $1,850/wk, #8 GATEWAY DISTRIBUTION at $1,750/wk, #9 DIVINE ENTERPRISES at $1,375/wk, #10 Diaz Stone & Pallet Inc. at $1,750/wk.
How drivers spend their time on the road in Pittsfield, Massachusetts
The route mix in Pittsfield, Massachusetts this month tilts OTR: 19% regional, 77% OTR, 3% local, 1% semi-local — drawn from active postings, not historical surveys.
Guaranteed pay is on offer at 2% of Pittsfield, Massachusetts postings; dedicated routes at 23%; take-truck-home at 77%. Pet-friendly policies appear at 62% and riders-allowed at 63%.
Where Pittsfield, Massachusetts differs from the Massachusetts baseline
| Pittsfield, Massachusetts | Massachusetts top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 48% | 43% | +5 pt |
| Pet-friendly fleets | 72% | 63% | +9 pt |
| Take-truck-home | 90% | 82% | +8 pt |
| Riders-allowed policies | 76% | 71% | +5 pt |
Source: Lanefinder index, May 2026
The largest gap is on pet-friendly fleets: Pittsfield, Massachusetts sits 9 points 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 owner-operator companies in Pittsfield, Massachusetts
- CDL driver salary in Pittsfield, Massachusetts
- Best trucking companies in Massachusetts
The methodology behind the rankings
Pay carriers in the same market against each other (30% of the score). Add a five-dimension FMCSA safety percentile from SAFER (25%). Score benefits based on whether the carrier hires W2 drivers or contractors (25%). Layer on employer responsiveness and fleet scale (20%). The weights are fixed and public. Updated May 2026.