Updated July 2026
Best Owner-Operator Companies in Medford, Massachusetts (July 2026)
Medford, Massachusetts has 492 active owner-operator carriers as of July 2026. The carriers ranked below are scored on real driver pay, FMCSA safety, benefits, and how they treat applicants. ROLLING ON WHEELS LLC leads with an average gross weekly revenue of $8,500. INLAND EMPIRE LLC follows at $7,875/week gross. Massachusetts freight runs on the I-90 / I-93 / I-95 metro grid through Boston, with Port of Boston handling bulk and container cargo and a major concentration of biotech and pharmaceutical manufacturing requiring cold-chain and hazmat lanes.
What changed in July 2026
We just started tracking monthly changes for this view. Check back next month to see how rankings have shifted.
Medford, Massachusetts's top owner-operator carriers right now
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 Medford, Massachusetts ranking with the strongest composite score across pay, safety, benefits, and operational signals. Pay sits above the 88th percentile in the Medford, Massachusetts market. On driver fitness, the carrier ranks in the 96th percentile per FMCSA SAFER data. ROLLING ON WHEELS LLC responds to driver applications more reliably than the Medford, Massachusetts median.
#2INLAND EMPIRE LLC — $7,875/wk
INLAND EMPIRE LLC's gross weekly revenue ranks in the 88th percentile across Medford, Massachusetts.
#3WINNERS TRANSPORTATION LLC — $2,437/wk
WINNERS TRANSPORTATION LLC's top FMCSA dimension is hours-of-service compliance, in the 96th percentile. WINNERS TRANSPORTATION LLC responds to driver applications more reliably than the Medford, Massachusetts median.
Also in the top 10: #4 TITANIUM AMERICAN TRUCKING INC at $6,250/wk, #5 Rickman Transport, LLC at $9,250/wk, #6 OVERLOG INC at $3,613/wk, #7 Ali Star Inc at $9,000/wk, #8 BB8 FREIGHT CO at $12,666/wk, #9 BLUE LIGHTNING LOGISTICS at $7,000/wk, #10 C & G TRANSPORTATION INC at $7,500/wk.
What Medford, Massachusetts drivers actually run
8% of Medford, Massachusetts's active CDL postings are regional and 92% are OTR; local plus semi-local accounts for the rest (0%).
Guaranteed pay is on offer at 2% of Medford, Massachusetts postings; dedicated routes at 28%; take-truck-home at 93%. Pet-friendly policies appear at 73% and riders-allowed at 71%.
Medford, Massachusetts vs Massachusetts: the numbers that diverge
Medford, Massachusetts's biggest divergence from Massachusetts is on average weekly pay, 9% above the state baseline.
Driving CDL in Massachusetts
Massachusetts freight runs on the I-90 / I-93 / I-95 grid through Boston, with the Port of Boston handling bulk and container cargo. A dense biotech and pharmaceutical manufacturing cluster around Cambridge / Boston / Worcester requires cold-chain and hazmat-eligible lanes. The Big Dig tunnels have truck-height and hazmat restrictions worth checking before routing. Boston congestion is consistently in the worst US tier. Cost of living is among the highest nationally. Massachusetts has a moderate flat state income tax with an added surtax on very high incomes (not relevant for most drivers).
Related guides
- Best trucking companies in Medford, Massachusetts
- CDL driver salary in Medford, Massachusetts
- Best owner-operator companies in Massachusetts
How we compile these rankings
Four weighted components. Compensation carries 30% and includes pay percentile, sign-on bonus tier, guaranteed-pay availability, and settlement frequency. FMCSA safety carries 25%, built from five SAFER dimensions. Benefits carry 25%, scored separately for W2 versus owner-operator carriers. Operational performance carries 20%, measuring application responsiveness and fleet scale. Updated July 2026.