Updated September 2026
Best Owner-Operator Companies in Portsmouth, Virginia (September 2026)
573 owner-operator carriers are hiring in Portsmouth, Virginia 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. Virginia freight is anchored by the Port of Virginia at Norfolk and Hampton Roads, the deepest commercial harbor on the East Coast (55 ft after the Gateway dredging program), with I-95 / I-64 / I-81 truck corridors connecting it to the mid-Atlantic and Southeast markets.
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 Portsmouth, Virginia compares to Virginia
| Portsmouth, Virginia | Virginia top 50 | Delta | |
|---|---|---|---|
| Average weekly pay | $6,287 | $5,276 | +19% |
| Sign-on bonus rate | 24% | 29% | -5 pt |
Source: Lanefinder index, September 2026
Among the figures above, average weekly pay is where Portsmouth, Virginia differs most from Virginia — 19% above statewide.
Where owner-operator pay is strongest in Portsmouth, Virginia 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 tops the Portsmouth, Virginia ranking with the strongest composite score across pay, safety, benefits, and operational signals. Pay sits above the 89th percentile in the Portsmouth, Virginia market. On driver fitness, the carrier ranks in the 87th percentile per FMCSA SAFER data. Driver applications get a faster-than-median response in Portsmouth, Virginia.
#2WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC's FMCSA score is strongest on driver fitness — 92nd percentile. WINNERS TRANSPORTATION LLC tracks as a responsive employer on application-response data.
#3LOAD MONSTER INC — $5,125/wk
LOAD MONSTER INC's FMCSA score is strongest on hours-of-service compliance — 96th percentile. Application-response data flags this carrier as a responsive employer.
Also in the top 10: #4 WESTERN MOUNTAIN TRANSPORT INC at $8,750/wk, #5 WIDER GROUP INC at $6,250/wk, #6 BLUE LIGHTNING LOGISTICS at $7,000/wk, #7 KILO METER LOGISTIC INC at $7,500/wk, #8 C & G TRANSPORTATION INC at $7,500/wk, #9 M&D TRANSPORT at $7,000/wk, #10 AIA TRUCKING INC at $3,450/wk.
How drivers spend their time on the road in Portsmouth, Virginia
9% of Portsmouth, Virginia's active CDL postings are regional and 90% are OTR; local plus semi-local accounts for the rest (1%).
Across Portsmouth, Virginia CDL postings: 2% with guaranteed pay, 27% dedicated, 93% take-truck-home, 72% pet-friendly, 71% riders-allowed.
Driving CDL in Virginia
Virginia freight is anchored by the Port of Virginia at Norfolk and Hampton Roads — the deepest commercial harbor on the East Coast and a top-tier US container gateway. The I-95 / I-64 / I-81 truck corridors connect Norfolk to mid-Atlantic and Southeast markets, with I-81 north-south through the Shenandoah Valley a major regional freight spine. Cost of living varies widely (high in Northern Virginia, moderate elsewhere). Virginia has a moderate graduated state income tax. Northern Virginia (DC suburbs) congestion is consistently top-tier; central and western VA is generally easier driving.
Related guides
- Best trucking companies in Portsmouth, Virginia
- CDL driver salary in Portsmouth, Virginia
- Best owner-operator companies in Virginia
Where this data comes from
Compensation, FMCSA safety, benefits, and operational performance — weighted 30, 25, 25, and 20 percent respectively. Compensation extends beyond headline pay to include sign-on bonus tier and settlement cadence. Benefits scoring differs by hiring type because the perks that matter to a W2 driver and a contractor are not the same. Updated September 2026.