Updated September 2026
Best Trucking Companies in Annapolis, Maryland (September 2026)
For W2 company drivers in Annapolis, Maryland, Lanefinder tracks 271 carriers as of September 2026. JK MOVING & STORAGE INC leads with an average weekly pay of $2,200. Big Foot Transport LLC follows at $2,650/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 September 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
How Annapolis, Maryland compares to Maryland
| Annapolis, Maryland | Maryland top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $1,960 | $1,884 | +4% |
| Sign-on bonus rate | 32% | 39% | -7 pt |
| Pet-friendly fleets | 78% | 55% | +23 pt |
| Riders-allowed policies | 80% | 61% | +19 pt |
| Take-truck-home | 90% | 73% | +17 pt |
| Dedicated routes | 26% | 39% | -13 pt |
Source: Lanefinder index, September 2026
The largest gap is on pet-friendly fleets: Annapolis, Maryland sits 23 points above the Maryland baseline.
Annapolis, Maryland's top trucking carriers right now
The top of the list is JK MOVING & STORAGE INC at $2,200/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1JK MOVING & STORAGE INC — $2,200/wk
JK MOVING & STORAGE INC leads the Annapolis, Maryland market on combined pay and ranking score this month. 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 unsafe-driving avoidance — 93rd percentile.
#2Big Foot Transport LLC — $2,650/wk
Big Foot Transport LLC's weekly pay ranks in the 98th percentile across Annapolis, Maryland. FMCSA composite safety lands in the 88th percentile. Driver applications get a faster-than-median response in Annapolis, Maryland.
#3Covenant Transport Inc — $1,762/wk
Covenant Transport Inc's FMCSA score is strongest on driver fitness — 99th percentile.
Also in the top 10: #4 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #5 KEYSTONE TRANSPORT SERVICES LLC at $1,965/wk, #6 ECM ENERGY SERVICES INC at $1,950/wk, #7 GATEWAY DISTRIBUTION at $1,750/wk, #8 Diaz Stone & Pallet 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 27%; take-truck-home at 74%. Pet-friendly policies appear at 61% and riders-allowed at 59%.
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 September 2026.