Updated September 2026
Best Owner-Operator Companies in Hagerstown, Maryland (September 2026)
581 owner-operator carriers are hiring in Hagerstown, Maryland this September 2026. RAY'S TRANSPORT INC leads with an average gross weekly revenue of $8,500 and an average $2,000 sign-on bonus. WINNERS TRANSPORTATION LLC follows at $2,657/week gross. 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.
Where Hagerstown, Maryland differs from the Maryland baseline
| Hagerstown, Maryland | Maryland top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,431 | $5,597 | +15% |
| Dedicated routes | 46% | 39% | +7 pt |
Source: Lanefinder index, September 2026
Hagerstown, Maryland's biggest divergence from Maryland is on average weekly pay, 15% above the state baseline.
The owner-operator carriers leading Hagerstown, Maryland this month
The top of the list is RAY'S TRANSPORT INC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1RAY'S TRANSPORT INC — $8,500/wk
RAY'S TRANSPORT INC leads the Hagerstown, Maryland market on combined gross revenue and ranking score this month. The carrier ranks in the 94th percentile for gross weekly revenue in Hagerstown, Maryland. Strongest FMCSA dimension is driver fitness — 87th percentile. Application-response data flags this carrier as a responsive employer.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is driver fitness, in the 92nd percentile. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Hagerstown, Maryland median.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. Driver applications get a faster-than-median response in Hagerstown, Maryland.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #6 WIDER GROUP INC at $6,250/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 KILO METER LOGISTIC INC at $7,500/wk, #9 C & G TRANSPORTATION INC at $7,500/wk, #10 AIA TRUCKING INC at $3,450/wk.
How drivers spend their time on the road in Hagerstown, Maryland
The route mix in Hagerstown, Maryland this month tilts OTR: 9% regional, 90% OTR, 1% local, 1% semi-local — drawn from active postings, not historical surveys.
Guaranteed pay is on offer at 2% of Hagerstown, Maryland postings; dedicated routes at 28%; take-truck-home at 92%. Pet-friendly policies appear at 72% and riders-allowed at 69%.
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 trucking companies in Hagerstown, Maryland
- CDL driver salary in Hagerstown, Maryland
- Best owner-operator companies in Maryland
How we compile these rankings
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.