Updated November 2026
Best Owner-Operator Companies in Annapolis, Maryland (November 2026)
Lanefinder is tracking 572 owner-operator carriers in Annapolis, Maryland (November 2026). ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $8,500. MONDO MOTION LLC follows at $9,250/week gross. 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
ROLLING ON WHEELS LLC at #1, MONDO MOTION LLC at #2, and MAYBACH INTERNATIONAL GROUP INC at #3 are new to the top 50 in Annapolis, Maryland. RAY'S TRANSPORT INC (was #1), ANTLER TRANSPORT LLC (was #2), and KILO METER LOGISTIC INC (was #8) left the top 50. Average weekly pay moved most at EXPRESS CR INC (up 18.2% from $2,750 to $3,250). Elsewhere in the top 50, 7 carriers joined, 7 left, and 32 changed rank.
All changes since October 2026
| Carrier | Last month | This month | Change |
|---|---|---|---|
| ROLLING ON WHEELS LLC | Not ranked | #1 | New |
| MONDO MOTION LLC | Not ranked | #2 | New |
| MAYBACH INTERNATIONAL GROUP INC | Not ranked | #3 | New |
| WINNERS TRANSPORTATION LLC | Not ranked | #4 | New |
| WIDER GROUP INC | #3 | #5 | Down 2 places |
| IKKO LOGISTICS LLC | #7 | #6 | Up 1 place |
| BLUE LIGHTNING LOGISTICS | #4 | #7 | Down 3 places |
| Ali Star Inc | #5 | #8 | Down 3 places |
| C & G TRANSPORTATION INC | #6 | #9 | Down 3 places |
| M&D TRANSPORT | #9 | #10 | Down 1 place |
| JK MOVING & STORAGE INC | #13 | #12 | Up 1 place |
| TITAN FREIGHT LINES INC | #10 | #13 | Down 3 places |
| Goldway Trans LLC | #12 | #14 | Down 2 places |
| HERMES NVC CORP | Not ranked | #15 | New |
| ITF Group | #15 | #16 | Down 1 place |
| LUXOR DRIVE INC | #14 | #17 | Down 3 places |
| FIVE STAR TRUCKING INC | #16 | #18 | Down 2 places |
| WLC GROUP INC | Not ranked | #19 | New |
| CO Lines Inc | #17 | #20 | Down 3 places |
| SUPERTRANSPORT LLC | #22 | #21 | Up 1 place |
| BIG JOHN EXPEDITED INC | #18 | #22 | Down 4 places |
| LEGACY CARGO LLC | #21 | #23 | Down 2 places |
| SOUTHLAND TRANSPORTATION | #25 | #24 | Up 1 place |
| STEPANOV TRUCKING LLC | Not ranked | #25 | New |
| J & J Oil LLC | #19 | #26 | Down 7 places |
| Blue Diamond Transportation LLC | #28 | #27 | Up 1 place |
| EXPRESS CR INC | #31 | #28 | Up 3 placesweekly pay up 18.2% ($2,750 → $3,250) |
| SUNGOR TRANSPORTATION INC | #24 | #29 | Down 5 places |
| COMMONWEALTH TRANSPORTATION LLC | #34 | #31 | Up 3 places |
| A & H INC | #35 | #32 | Up 3 places |
| AS TRANSPORTATION INC | Not ranked | #33 | New |
| OTRL Recruiting | Not ranked | #34 | New |
| D & H CATTLE COMPANY LLC | #33 | #35 | Down 2 places |
| LINESTAR EXPRESS LLC | #32 | #37 | Down 5 places |
| STAR PARTNERS LLC | Not ranked | #38 | New |
| EOS Trucking Inc. | #37 | #39 | Down 2 places |
| LANDSHARK LOGISTICS GROUP LLC | #38 | #40 | Down 2 places |
| MILESTONE TRUCKING LLC | #39 | #41 | Down 2 places |
| AN ENTERPRISE INC | #41 | #43 | Down 2 places |
| HORIZON TRANSPORTATION | #40 | #44 | Down 4 places |
| BREEZE TRANSPORTATION INCORPORATED | #44 | #45 | Down 1 place |
| VITAL TRANSPORTATION CORP | #43 | #46 | Down 3 places |
| REVEL TRANSPORT LLC | #46 | #47 | Down 1 place |
| RAY'S TRANSPORT INC | #1 | Not ranked | Dropped out |
| ANTLER TRANSPORT LLC | #2 | Not ranked | Dropped out |
| KILO METER LOGISTIC INC | #8 | Not ranked | Dropped out |
| A&M CARRIERS INC | #20 | Not ranked | Dropped out |
| BLACK EAGLE EXPRESS LLC | #23 | Not ranked | Dropped out |
| MAX MOVE LLC | #26 | Not ranked | Dropped out |
| DOGE Trucking LLC | #27 | Not ranked | Dropped out |
| WESTERN MOUNTAIN TRANSPORT INC | #29 | Not ranked | Dropped out |
| STRAIGHT LOGISTICS INC | #45 | Not ranked | Dropped out |
| TXI Logistics | #47 | Not ranked | Dropped out |
Where owner-operator pay is strongest in Annapolis, Maryland this month
The top of the list is ROLLING ON WHEELS LLC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $8,500/wk
ROLLING ON WHEELS LLC tops the Annapolis, Maryland ranking with the strongest composite score across pay, safety, benefits, and operational signals. The carrier ranks in the 94th percentile for gross weekly revenue in Annapolis, Maryland. Top FMCSA dimension here is driver fitness, in the 87th percentile. ROLLING ON WHEELS LLC tracks as a responsive employer on application-response data.
#2MONDO MOTION LLC — $9,250/wk
MONDO MOTION LLC makes its first-time appearance in Annapolis, Maryland's ranking this month. The carrier ranks in the 96th percentile for gross weekly revenue in Annapolis, Maryland. Strongest FMCSA dimension is hours-of-service compliance — 98th percentile. The carrier tracks as a responsive employer on Lanefinder's data.
#3MAYBACH INTERNATIONAL GROUP INC — $3,025/wk
MAYBACH INTERNATIONAL GROUP INC makes its first-time appearance in Annapolis, Maryland's ranking this month. MAYBACH INTERNATIONAL GROUP INC's FMCSA score is strongest on driver fitness — 96th percentile. Lanefinder's application data flags MAYBACH INTERNATIONAL GROUP INC as a responsive employer.
Also in the top 10: #4 WINNERS TRANSPORTATION LLC at $2,657/wk, #5 WIDER GROUP INC at $6,250/wk, #6 IKKO LOGISTICS LLC at $7,500/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 Ali Star Inc at $10,000/wk, #9 C & G TRANSPORTATION INC at $7,500/wk, #10 M&D TRANSPORT at $7,000/wk.
What Annapolis, Maryland drivers actually run
Of active CDL postings in Annapolis, Maryland this month, 10% are regional and 89% are OTR (long-haul). Local and semi-local routes account for the remaining 1%.
Across Annapolis, Maryland CDL postings: 1% with guaranteed pay, 29% dedicated, 92% take-truck-home, 71% pet-friendly, 68% riders-allowed.
How Annapolis, Maryland compares to Maryland
| Annapolis, Maryland | Maryland top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,422 | $5,238 | +23% |
| Dedicated routes | 52% | 43% | +9 pt |
| Riders-allowed policies | 86% | 80% | +6 pt |
Source: Lanefinder index, November 2026
Annapolis, Maryland's biggest divergence from Maryland is on average weekly pay, 23% above the state baseline.
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 trucking companies in Annapolis, Maryland
- CDL driver salary in Annapolis, Maryland
- Best owner-operator companies in Maryland
How we compile these rankings
Lanefinder's ranking algorithm weights compensation at 30%, FMCSA SAFER safety at 25%, benefits at 25%, and operational performance at 20%. Compensation reflects pay percentile plus sign-on bonus, guaranteed pay, and settlement-frequency adjustments. Benefits scoring is hiring-type-aware. Operational performance comes mostly from how carriers handle real driver applications. Updated November 2026.