Updated November 2026
Best Trucking Companies in Maryland (November 2026)
Maryland's W2 trucking market includes 464 active carriers as of November 2026. HandledNow LLC leads with an average weekly pay of $1,800 and an average $2,500 sign-on bonus. Herrington Transportation Inc. follows at $2,000/week. Maryland freight flows through Port of Baltimore — a major East Coast container and auto-import port (whose channel reopened within months of the 2024 Key Bridge collapse) — and along the I-95 / I-70 / I-695 Beltway corridor connecting mid-Atlantic manufacturing and DC-metro distribution.
What changed in November 2026
McLeod Express LLC at #3, SAFE WAY CARRIER LLC at #7, and Mountain States L.P. Gas at #9 are new to the top 50 in Maryland. Biggest climbs: Herrington Transportation Inc. (#38 → #2) and True Transport Inc. (#20 → #5). Biggest falls: LAWRENCE TRANSPORTATION COMPANY (#3 → #27) and KEYSTONE TRANSPORT SERVICES LLC (#8 → #29). Average weekly pay moved most at KEYSTONE TRANSPORT SERVICES LLC (down 39.6% from $1,965 to $1,187). Elsewhere in the top 50, 5 carriers joined, 8 left, and 28 changed rank.
All changes since October 2026
| Carrier | Last month | This month | Change |
|---|---|---|---|
| Herrington Transportation Inc. | #38 | #2 | Up 36 places |
| McLeod Express LLC | Not ranked | #3 | New |
| Pipco Transportation | #2 | #4 | Down 2 places |
| True Transport Inc. | #20 | #5 | Up 15 places |
| HAZMAT ENVIRONMENTAL GROUP INC | #4 | #6 | Down 2 places |
| SAFE WAY CARRIER LLC | Not ranked | #7 | New |
| Covenant Transport Inc | #5 | #8 | Down 3 places |
| Mountain States L.P. Gas | Not ranked | #9 | New |
| DICK LAVY TRUCKING | Not ranked | #10 | New |
| INSULATION COMPANY OF AMERICA LLC | #9 | #11 | Down 2 places |
| PRAIRIE FIELD SERVICES LLC | #7 | #12 | Down 5 places |
| Maumee Express, Inc. | #6 | #13 | Down 7 places |
| GATEWAY DISTRIBUTION | #15 | #14 | Up 1 place |
| JK MOVING & STORAGE INC | #11 | #15 | Down 4 places |
| C & G TRANSPORTATION INC | #14 | #16 | Down 2 places |
| PREMIER TRANSPORTATION | #12 | #17 | Down 5 places |
| TAYLOR TRUCK LINE INC | Not ranked | #18 | New |
| ROAD SCHOLAR TRANSPORTATION LLC | #10 | #19 | Down 9 places |
| JS HELWIG & SON LLC | #18 | #20 | Down 2 places |
| SECOR LOGISTICS LLC | #13 | #21 | Down 8 places |
| Diaz Stone & Pallet Inc. | #17 | #22 | Down 5 places |
| G-DIAMOND TRANSPORT INC | #19 | #23 | Down 4 places |
| GEORGE'S FOODS LLC | #16 | #24 | Down 8 places |
| ELBERTA LOGISTICS INTERNATIONAL LLC | #22 | #25 | Down 3 places |
| ALBA TRANS INC | #21 | #26 | Down 5 places |
| LAWRENCE TRANSPORTATION COMPANY | #3 | #27 | Down 24 places |
| MC CARRIER LLC | #23 | #28 | Down 5 places |
| KEYSTONE TRANSPORT SERVICES LLC | #8 | #29 | Down 21 placesweekly pay down 39.6% ($1,965 → $1,187); added dedicated routes |
| HOLLAND ENTERPRISES INC | #28 | #30 | Down 2 places |
| CUSTOM TRANSPORT INC | #24 | #31 | Down 7 places |
| A & H INC | #37 | #33 | Up 4 places |
| RIVER CITY TRANSPORT INC | #27 | #34 | Down 7 places |
| KAISER TRANSPORT INC | #30 | #35 | Down 5 places |
| R B HUMPHREYS INC | Not ranked | #36 | New |
| AFC Transport, Inc | #36 | #37 | Down 1 place |
| ARCTIC EXPRESS | #33 | #38 | Down 5 places |
| LUCKY WORLD INC | Not ranked | #40 | New |
| HUTCHINSON TRUCKING LLC | #43 | #42 | Up 1 place |
| MARK IV TRANSPORTATION & LOGISTICS INC | #44 | #43 | Up 1 place |
| StaffWorthy | Not ranked | #44 | New |
| H & M TRUCKING INC | #25 | Not ranked | Dropped out |
| TRANSERVICE LOGISTICS INC | #26 | Not ranked | Dropped out |
| WILLIAMS PRESTIGE ENTERPRISE | #29 | Not ranked | Dropped out |
| AIR-GROUND XPRESS INC | #31 | Not ranked | Dropped out |
| Safeway Trucking Corporation | #34 | Not ranked | Dropped out |
| Hiltz Propane Systems, Inc | #35 | Not ranked | Dropped out |
| B & T EXPRESS INC | #40 | Not ranked | Dropped out |
| ANTLER TRANSPORT LLC | #42 | Not ranked | Dropped out |
The trucking companies leading Maryland this month
The top of the list is HandledNow LLC at $1,800/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1HandledNow LLC — $1,800/wk
HandledNow LLC is number-one in Maryland this month on the composite ranking. HandledNow LLC ranks in the 99th percentile for driver fitness on FMCSA SAFER data. HandledNow LLC tracks as a responsive employer on application-response data.
#2Herrington Transportation Inc. — $2,000/wk
Herrington Transportation Inc. climbed from #38 to #2 this month — one of the biggest moves in Maryland. Herrington Transportation Inc.'s weekly pay ranks in the 92nd percentile across Maryland. The carrier tracks as a responsive employer on Lanefinder's data.
#3McLeod Express LLC — $1,550/wk
McLeod Express LLC debuts in the Maryland top 50 this month — it wasn't tracked here last month. McLeod Express LLC's top FMCSA dimension is unsafe-driving avoidance, in the 94th percentile. McLeod Express LLC guarantees weekly pay — useful when freight slows down.
McLeod Express LLC is the only Maryland top-10 carrier that guarantees weekly pay regardless of miles run.
Also in the top 10: #4 Pipco Transportation at $1,900/wk, #5 True Transport Inc. at $2,250/wk, #6 HAZMAT ENVIRONMENTAL GROUP INC at $1,975/wk, #7 SAFE WAY CARRIER LLC at $2,100/wk, #8 Covenant Transport Inc at $1,762/wk, #9 Mountain States L.P. Gas at $2,000/wk, #10 DICK LAVY TRUCKING at $1,950/wk.
What Maryland drivers actually run
Of active CDL postings in Maryland this month, 29% are regional and 56% are OTR (long-haul). Local and semi-local routes account for the remaining 15%.
Across Maryland CDL postings: 2% with guaranteed pay, 29% dedicated, 67% take-truck-home, 54% pet-friendly, 53% riders-allowed.
Driving CDL in Maryland
Maryland freight flows through the Port of Baltimore — a major East Coast container and auto-import port (the 2024 Key Bridge collapse closed the channel for about two months; the replacement bridge is due around 2030) — and along the I-95 / I-70 / I-695 (Baltimore Beltway) corridor connecting mid-Atlantic manufacturing and DC-metro distribution. The Beltway is a recurring truck bottleneck. Cost of living is high and state income tax is moderate-to-high depending on county add-ons. Eastern Shore freight (poultry processing especially) is a distinct regional segment. The Bay Bridge wind restrictions and weight rules complicate Eastern Shore route timing.
Related guides
- Best owner-operator companies in Maryland
- CDL driver salary in Maryland
- Best trucking companies in the United States
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 November 2026.