Updated November 2026
Best Trucking Companies in Annapolis, Maryland (November 2026)
For W2 company drivers in Annapolis, Maryland, Lanefinder tracks 273 carriers as of November 2026. Herrington Transportation Inc. leads with an average weekly pay of $2,000. True Transport Inc. follows at $2,250/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
Mountain States L.P. Gas at #4 and TAYLOR TRUCK LINE INC at #8 are new to the top 50 in Annapolis, Maryland. Biggest climb: Herrington Transportation Inc. (#27 → #1). Biggest falls: LAWRENCE TRANSPORTATION COMPANY (#1 → #14) and REISCH TRUCKING INC (#36 → #47). KEYSTONE TRANSPORT SERVICES LLC (was #5) left the top 50. Elsewhere in the top 50, 3 carriers joined, 4 left, and 33 changed rank.
All changes since October 2026
Annapolis, Maryland's top trucking carriers right now
The top of the list is Herrington Transportation Inc. at $2,000/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1Herrington Transportation Inc. — $2,000/wk
Herrington Transportation Inc. tops the Annapolis, Maryland ranking with the strongest composite score across pay, safety, benefits, and operational signals. Herrington Transportation Inc. sits in the 90th percentile for weekly pay among Annapolis, Maryland carriers. Lanefinder's application data flags Herrington Transportation Inc. as a responsive employer.
#2True Transport Inc. — $2,250/wk
True Transport Inc. rose 8 positions month-over-month, from #10 to #2. The carrier ranks in the 95th percentile for weekly pay in Annapolis, Maryland. True Transport Inc. ranks in the 98th percentile for unsafe-driving avoidance on FMCSA SAFER data.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC sits in the 93rd percentile for weekly pay among Annapolis, Maryland carriers. JK MOVING & STORAGE INC's FMCSA score is strongest on vehicle maintenance — 94th percentile.
Also in the top 10: #4 Mountain States L.P. Gas at $2,000/wk, #5 Covenant Transport Inc at $1,762/wk, #6 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #7 GATEWAY DISTRIBUTION at $1,750/wk, #8 TAYLOR TRUCK LINE INC at $1,750/wk, #9 JS HELWIG & SON LLC at $1,850/wk, #10 ALBA TRANS INC at $3,000/wk.
What Annapolis, Maryland drivers actually run
21% of Annapolis, Maryland's active CDL postings are regional and 69% are OTR; local plus semi-local accounts for the rest (10%).
Guaranteed pay is on offer at 2% of Annapolis, Maryland postings; dedicated routes at 28%; take-truck-home at 74%. Pet-friendly policies appear at 61% and riders-allowed at 59%.
How Annapolis, Maryland compares to Maryland
| Annapolis, Maryland | Maryland top 50 | Delta | |
|---|---|---|---|
| Sign-on bonus rate | 36% | 47% | -11 pt |
| Dedicated routes | 28% | 41% | -13 pt |
| Pet-friendly fleets | 78% | 65% | +13 pt |
| Riders-allowed policies | 82% | 73% | +9 pt |
| Take-truck-home | 90% | 82% | +8 pt |
Source: Lanefinder index, November 2026
The largest gap is on dedicated routes: Annapolis, Maryland sits 13 points below the Maryland 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 owner-operator companies in Annapolis, Maryland
- CDL driver salary in Annapolis, Maryland
- Best trucking companies in Maryland
Where this data comes from
Compensation (30%): pay percentile + sign-on bonus + guaranteed pay + settlement frequency. FMCSA safety (25%): weighted percentile across vehicle maintenance, unsafe driving, hours-of-service, driver fitness, and controlled substances. Benefits (25%): hiring-type-aware. Operational (20%): driver-application responsiveness, modulated by fleet scale. Updated November 2026.