Updated November 2026
Best Trucking Companies in Pittsfield, Massachusetts (November 2026)
Pittsfield, Massachusetts, November 2026: 236 active W2 trucking carriers. HandledNow LLC leads with an average weekly pay of $1,900 and an average $5,000 sign-on bonus. Herrington Transportation Inc. follows at $2,000/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 the nation's largest life-sciences cluster generating cold-chain and hazmat lanes.
What changed in November 2026
SAFE WAY CARRIER LLC at #4, Mountain States L.P. Gas at #6, and TAYLOR TRUCK LINE INC at #10 are new to the top 50 in Pittsfield, Massachusetts. Biggest climb: Herrington Transportation Inc. (#26 → #2). Biggest fall: REISCH TRUCKING INC (#32 → #45). Elsewhere in the top 50, 3 carriers joined, 6 left, and 40 changed rank.
All changes since October 2026
| Carrier | Last month | This month | Change |
|---|---|---|---|
| Herrington Transportation Inc. | #26 | #2 | Up 24 places |
| True Transport Inc. | #6 | #3 | Up 3 places |
| SAFE WAY CARRIER LLC | Not ranked | #4 | New |
| JK MOVING & STORAGE INC | #2 | #5 | Down 3 places |
| Mountain States L.P. Gas | Not ranked | #6 | New |
| Covenant Transport Inc | #3 | #7 | Down 4 places |
| PRAIRIE FIELD SERVICES LLC | #4 | #8 | Down 4 places |
| GATEWAY DISTRIBUTION | #5 | #9 | Down 4 places |
| TAYLOR TRUCK LINE INC | Not ranked | #10 | New |
| JS HELWIG & SON LLC | #8 | #11 | Down 3 places |
| G-DIAMOND TRANSPORT INC | #9 | #12 | Down 3 places |
| HARDING METALS INC | #10 | #13 | Down 3 places |
| ELBERTA LOGISTICS INTERNATIONAL LLC | #11 | #14 | Down 3 places |
| Diaz Stone & Pallet Inc. | #7 | #15 | Down 8 places |
| BRADY TRUCKING INC | #12 | #16 | Down 4 places |
| MC CARRIER LLC | #14 | #17 | Down 3 places |
| R B HUMPHREYS INC | Not ranked | #18 | New |
| M&D TRANSPORT | #16 | #19 | Down 3 places |
| A & H INC | #22 | #20 | Up 2 places |
| AFC Transport, Inc | #25 | #21 | Up 4 places |
| HOLLAND ENTERPRISES INC | #20 | #22 | Down 2 places |
| G & C FOOD DISTRIBUTORS & BROKERS INC | #24 | #23 | Up 1 place |
| WIN Waste Innovations | #19 | #24 | Down 5 places |
| NEIER INC | #17 | #25 | Down 8 places |
| RIVER CITY TRANSPORT INC | #18 | #26 | Down 8 places |
| Excel Trucking LLC | #21 | #27 | Down 6 places |
| ARCTIC EXPRESS | #23 | #29 | Down 6 places |
| LUCKY WORLD INC | Not ranked | #30 | New |
| CARGORX DRY CAPACITY | #29 | #31 | Down 2 places |
| AN ENTERPRISE INC | #27 | #32 | Down 5 places |
| Brenny Specialized Inc | #30 | #33 | Down 3 places |
| Prime Inc. | #31 | #34 | Down 3 places |
| StaffWorthy | Not ranked | #35 | New |
| CTK LOGISTICS LLC | #33 | #36 | Down 3 places |
| Cross Integrated Transport, LLC | #34 | #37 | Down 3 places |
| NTA, LTD. | #35 | #38 | Down 3 places |
| VITAL TRANSPORTATION CORP | #38 | #39 | Down 1 place |
| DAIM Trucking | #36 | #40 | Down 4 places |
| Bakers Express | #39 | #41 | Down 2 places |
| K & R TRANSPORT LLC | #40 | #42 | Down 2 places |
| S & R TRANSPORTATION LLC | #42 | #43 | Down 1 place |
| EAGLE EYE TRUCK LINES LLC | #41 | #44 | Down 3 places |
| REISCH TRUCKING INC | #32 | #45 | Down 13 places |
| LIBERTY HAULERS INC | #43 | #46 | Down 3 places |
| Parks Motor Group Inc | #44 | #47 | Down 3 places |
| 1 MTX LLC | #45 | #48 | Down 3 places |
| BROADWATER LOGISTICS & TRANSPORTATION INC | #47 | #49 | Down 2 places |
| HORIZON TRANSPORTATION | #49 | #50 | Down 1 place |
| H & M TRUCKING INC | #13 | Not ranked | Dropped out |
| WILLIAMS PRESTIGE ENTERPRISE | #15 | Not ranked | Dropped out |
| STONE TRANSPORT | #37 | Not ranked | Dropped out |
| KZY Logistics LLC | #46 | Not ranked | Dropped out |
| NAJJAR BROTHERS LLC | #48 | Not ranked | Dropped out |
| TRANSMASTER TRANSPORT LLC | #50 | Not ranked | Dropped out |
Pittsfield, Massachusetts's top trucking carriers right now
The top of the list is HandledNow LLC at $1,900/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1HandledNow LLC — $1,900/wk
HandledNow LLC is number-one in Pittsfield, Massachusetts this month on the composite ranking. HandledNow LLC's FMCSA score is strongest on driver fitness — 99th percentile. Driver applications get a faster-than-median response in Pittsfield, Massachusetts.
The top sign-on bonus in Pittsfield, Massachusetts's top 10 is HandledNow LLC's — $5,000.
#2Herrington Transportation Inc. — $2,000/wk
Herrington Transportation Inc. climbed from #26 to #2 this month — one of the biggest moves in Pittsfield, Massachusetts. Herrington Transportation Inc. sits in the 89th percentile for weekly pay among Pittsfield, Massachusetts carriers. Lanefinder's application data flags Herrington Transportation Inc. as a responsive employer.
#3True Transport Inc. — $2,250/wk
True Transport Inc. sits in the 95th percentile for weekly pay among Pittsfield, Massachusetts carriers. Strongest FMCSA dimension is unsafe-driving avoidance — 98th percentile.
For pure pay maximization, True Transport Inc. beats the #1-ranked carrier weekly at $2,250.
Also in the top 10: #4 SAFE WAY CARRIER LLC at $2,100/wk, #5 JK MOVING & STORAGE INC at $2,200/wk, #6 Mountain States L.P. Gas at $2,000/wk, #7 Covenant Transport Inc at $1,762/wk, #8 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #9 GATEWAY DISTRIBUTION at $1,750/wk, #10 TAYLOR TRUCK LINE 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: 20% regional, 76% 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 62%.
Where Pittsfield, Massachusetts differs from the Massachusetts baseline
| Pittsfield, Massachusetts | Massachusetts top 50 | Delta | |
|---|---|---|---|
| Take-truck-home | 88% | 78% | +10 pt |
| Pet-friendly fleets | 72% | 64% | +8 pt |
| Riders-allowed policies | 78% | 72% | +6 pt |
Source: Lanefinder index, November 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 a recurring truck bottleneck. 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 November 2026.