Updated September 2026
Best Trucking Companies in Pittsfield, Massachusetts (September 2026)
Pittsfield, Massachusetts, September 2026: 232 active W2 trucking carriers. JK MOVING & STORAGE INC leads with an average weekly pay of $2,200. Covenant Transport Inc follows at $1,762/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 September 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 JK MOVING & STORAGE INC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC is number-one in Pittsfield, Massachusetts this month on the composite ranking. 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 93rd percentile.
#2Covenant Transport Inc — $1,762/wk
Covenant Transport Inc's top FMCSA dimension is driver fitness, in the 99th percentile.
#3HandledNow LLC — $1,900/wk
HandledNow LLC's FMCSA score is strongest on driver fitness — 98th percentile.
Also in the top 10: #4 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #5 GATEWAY DISTRIBUTION at $1,750/wk, #6 Diaz Stone & Pallet Inc. at $1,750/wk, #7 JS HELWIG & SON LLC at $1,850/wk, #8 True Transport Inc. at $2,250/wk, #9 G-DIAMOND TRANSPORT INC at $2,045/wk, #10 HARDING METALS INC at $2,300/wk.
How drivers spend their time on the road in Pittsfield, Massachusetts
The route mix in Pittsfield, Massachusetts this month tilts OTR: 20% regional, 75% 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 25%; take-truck-home at 75%. Pet-friendly policies appear at 60% and riders-allowed at 61%.
Where Pittsfield, Massachusetts differs from the Massachusetts baseline
| Pittsfield, Massachusetts | Massachusetts top 50 | Delta | |
|---|---|---|---|
| Take-truck-home | 88% | 78% | +10 pt |
| Pet-friendly fleets | 70% | 62% | +8 pt |
| Riders-allowed policies | 78% | 70% | +8 pt |
Source: Lanefinder index, September 2026
The largest gap is on take-truck-home: Pittsfield, Massachusetts sits 10 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 September 2026.