Updated July 2026
Best Owner-Operator Companies in Bridgeport, Connecticut (July 2026)
514 owner-operator carriers are hiring in Bridgeport, Connecticut this July 2026. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $8,500. INLAND EMPIRE LLC follows at $7,875/week gross. Connecticut freight moves on I-95 and I-91 / I-84 connecting to the Northeast corridor, with Port of New Haven handling petroleum and heating oil (with breakbulk as a secondary segment) and a dense concentration of aerospace and defense manufacturing.
What changed in July 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
The owner-operator carriers leading Bridgeport, Connecticut this month
The top of the list is ROLLING ON WHEELS LLC at $8,500/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1ROLLING ON WHEELS LLC — $8,500/wk
ROLLING ON WHEELS LLC tops the Bridgeport, Connecticut ranking with the strongest composite score across pay, safety, benefits, and operational signals. Pay sits above the 88th percentile in the Bridgeport, Connecticut market. ROLLING ON WHEELS LLC's FMCSA score is strongest on driver fitness — 96th percentile. Lanefinder's application data flags ROLLING ON WHEELS LLC as a responsive employer.
#2INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC sits in the 88th percentile for gross weekly revenue among Bridgeport, Connecticut carriers.
#3WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC ranks in the 96th percentile for hours-of-service compliance on FMCSA SAFER data. Lanefinder's application data flags WINNERS TRANSPORTATION LLC as a responsive employer.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 OVERLOG INC at $3,613/wk, #6 Ali Star Inc at $10,000/wk, #7 BLUE LIGHTNING LOGISTICS at $7,000/wk, #8 BB8 FREIGHT CO at $12,666/wk, #9 C & G TRANSPORTATION INC at $7,500/wk, #10 MEGA TRUCKS INC at $13,500/wk.
Lane mix and benefits across Bridgeport, Connecticut
8% of Bridgeport, Connecticut's active CDL postings are regional and 91% are OTR; local plus semi-local accounts for the rest (1%).
Guaranteed pay is on offer at 2% of Bridgeport, Connecticut postings; dedicated routes at 28%; take-truck-home at 92%. Pet-friendly policies appear at 73% and riders-allowed at 69%.
Bridgeport, Connecticut vs Connecticut: the numbers that diverge
Bridgeport, Connecticut's biggest divergence from Connecticut is on average weekly pay, 8% above the state baseline.
Driving CDL in Connecticut
Connecticut CDL work is mostly last-mile and short-haul on the dense I-95 / I-91 / I-84 metro grid feeding the Northeast corridor. The Port of New Haven handles breakbulk; aerospace and defense manufacturing (Pratt & Whitney in East Hartford, Sikorsky in Stratford, plus RTX-related supplier networks) generate high-value freight. Cost of living is among the highest in the country and state income tax is high. Many drivers based here run out-of-state lanes to keep the math working. Truck-route restrictions on parkways and dense urban congestion make CT one of the higher-overhead states to operate in.
Related guides
- Best trucking companies in Bridgeport, Connecticut
- CDL driver salary in Bridgeport, Connecticut
- Best owner-operator companies in Connecticut
How we compile these rankings
Rankings combine four signals: compensation (30%) including pay percentile, sign-on bonuses, guaranteed pay, and settlement frequency; FMCSA safety (25%); benefits (25%) scored differently for W2 vs owner-operator carriers; and operational performance (20%) measuring employer responsiveness and fleet scale. Recomputed monthly from real active job postings. Updated July 2026.