Updated May 2026
Best Trucking Companies in Annapolis, Maryland (May 2026)
For W2 company drivers in Annapolis, Maryland, Lanefinder tracks 276 carriers as of May 2026. KEEP TRUCKING LLC leads with an average weekly pay of $2,200. True Transport Inc. follows at $2,250/week. Maryland freight flows through Port of Baltimore — a major East Coast container and auto-import port (recovering from 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 May 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Annapolis, Maryland's top trucking carriers right now
The top of the list is KEEP TRUCKING LLC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1KEEP TRUCKING LLC — $2,200/wk
KEEP TRUCKING 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 weekly pay in Annapolis, Maryland. KEEP TRUCKING LLC ranks in the 88th percentile for controlled-substances compliance on FMCSA SAFER data. Application-response data flags this carrier as a responsive employer.
#2True Transport Inc. — $2,250/wk
True Transport Inc. pays above the 91st percentile on weekly pay for the Annapolis, Maryland market. True Transport Inc. ranks in the 99th percentile for unsafe-driving avoidance on FMCSA SAFER data. The carrier tracks as a responsive employer on Lanefinder's data.
Despite ranking below #1, True Transport Inc. outpays the leader on weekly average — $2,250/week.
#3JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC sits in the 94th percentile for weekly pay among Annapolis, Maryland carriers. JK MOVING & STORAGE INC's FMCSA score is strongest on unsafe-driving avoidance — 94th percentile.
Also in the top 10: #4 Covenant Transport Inc at $1,762/wk, #5 HMD TRUCKING INC at $1,800/wk, #6 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #7 ECM ENERGY SERVICES INC at $1,950/wk, #8 GATEWAY DISTRIBUTION at $1,750/wk, #9 JS HELWIG & SON LLC at $1,850/wk, #10 Diaz Stone & Pallet Inc. at $1,750/wk.
What Annapolis, Maryland drivers actually run
20% of Annapolis, Maryland's active CDL postings are regional and 71% are OTR; local plus semi-local accounts for the rest (9%).
Guaranteed pay is on offer at 1% of Annapolis, Maryland postings; dedicated routes at 27%; take-truck-home at 74%. Pet-friendly policies appear at 60% and riders-allowed at 60%.
How Annapolis, Maryland compares to Maryland
| Annapolis, Maryland | Maryland top 50 | Delta | |
|---|---|---|---|
| Take-truck-home | 90% | 80% | +10 pt |
| Pet-friendly fleets | 70% | 63% | +7 pt |
Source: Lanefinder index, May 2026
The largest gap is on take-truck-home: Annapolis, Maryland sits 10 points above the Maryland baseline.
Driving CDL in Maryland
Maryland freight flows through the Port of Baltimore — a major East Coast container and auto-import port (recovering from the 2024 Key Bridge collapse) — and along the I-95 / I-70 / I-695 (Baltimore Beltway) corridor connecting mid-Atlantic manufacturing and DC-metro distribution. The Beltway is consistently top-tier in US congestion. 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 May 2026.