Updated May 2026
Best Trucking Companies in Maryland (May 2026)
Maryland's W2 trucking market includes 468 active 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.
The trucking companies leading Maryland this month
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 leads the Maryland market on combined pay and ranking score this month. Pay sits above the 91st percentile in the Maryland market. KEEP TRUCKING LLC's top FMCSA dimension is controlled-substances compliance, in the 88th percentile. Driver applications get a faster-than-median response in Maryland.
#2True Transport Inc. — $2,250/wk
True Transport Inc.'s weekly pay ranks in the 97th percentile across Maryland. True Transport Inc.'s top FMCSA dimension is unsafe-driving avoidance, in the 99th percentile. Lanefinder's application data flags True Transport Inc. as a responsive employer.
True Transport Inc. doesn't top the ranking but offers higher weekly pay than #1 — $2,250/week.
#3Covenant Transport Inc — $1,762/wk
Covenant Transport Inc's top FMCSA dimension is hours-of-service compliance, in the 94th percentile.
Also in the top 10: #4 HMD TRUCKING INC at $1,800/wk, #5 PRAIRIE FIELD SERVICES LLC at $1,750/wk, #6 Maumee Express, Inc. at $1,925/wk, #7 ECM ENERGY SERVICES INC at $1,950/wk, #8 GATEWAY DISTRIBUTION at $1,750/wk, #9 JK MOVING & STORAGE INC at $1,800/wk, #10 YARBROUGH TRANSFER COMPANY at $1,850/wk.
What Maryland drivers actually run
Of active CDL postings in Maryland this month, 27% are regional and 58% are OTR (long-haul). Local and semi-local routes account for the remaining 15%.
Across Maryland CDL postings: 1% with guaranteed pay, 27% 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 (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 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 May 2026.