Updated September 2026
Best Owner-Operator Companies in Bend, Oregon (September 2026)
As of September 2026, 432 carriers in Bend, Oregon are posting active jobs for owner-operators. WINNERS TRANSPORTATION LLC leads with an average gross weekly revenue of $2,657 and an average $2,142 sign-on bonus. WESTERN MOUNTAIN TRANSPORT INC follows at $8,500/week gross. Oregon freight moves on I-5 north-south through Portland and Eugene, with the Port of Portland handling bulk grain and auto imports, and agricultural and forestry exports — wheat, hay, lumber — generating significant outbound volumes.
What changed in September 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 Bend, Oregon this month
The top of the list is WINNERS TRANSPORTATION LLC at $2,657/week. A few names below the top earn more on a weekly-pay basis but rank lower on the composite.
#1WINNERS TRANSPORTATION LLC — $2,657/wk
WINNERS TRANSPORTATION LLC leads the Bend, Oregon market on combined gross revenue and ranking score this month. WINNERS TRANSPORTATION LLC ranks in the 92nd percentile for driver fitness on FMCSA SAFER data. Application-response data flags this carrier as a responsive employer.
#2WESTERN MOUNTAIN TRANSPORT INC — $8,500/wk
WESTERN MOUNTAIN TRANSPORT INC pays above the 89th percentile on gross weekly revenue for the Bend, Oregon market. WESTERN MOUNTAIN TRANSPORT INC's FMCSA score is strongest on driver fitness — 93rd percentile. WESTERN MOUNTAIN TRANSPORT INC responds to driver applications more reliably than the Bend, Oregon median.
#3Rickman Transport, LLC — $9,250/wk
Rickman Transport, LLC's gross weekly revenue ranks in the 96th percentile across Bend, Oregon. Top FMCSA dimension here is unsafe-driving avoidance, in the 91st percentile.
Rickman Transport, LLC leads Bend, Oregon's top 10 on sign-on bonus, advertising $6,000 for new drivers.
Also in the top 10: #4 GNS TRUCKING INC at $9,000/wk, #5 Ali Star Inc at $10,000/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 TP TRUCKING at $8,500/wk, #10 TITAN FREIGHT LINES INC at $8,500/wk.
How drivers spend their time on the road in Bend, Oregon
The route mix in Bend, Oregon this month tilts OTR: 7% regional, 92% OTR, 0% local, 1% semi-local — drawn from active postings, not historical surveys.
Across Bend, Oregon CDL postings: 1% with guaranteed pay, 26% dedicated, 92% take-truck-home, 74% pet-friendly, 73% riders-allowed.
How Bend, Oregon compares to Oregon
Bend, Oregon's biggest divergence from Oregon is on average weekly pay, 9% above the state baseline.
Driving CDL in Oregon
Oregon freight moves on I-5 north-south through the Willamette Valley (Portland-Salem-Eugene), with the Port of Portland handling bulk grain (one of the largest US wheat-export terminals) and auto imports. Agricultural and forestry exports — wheat, hay, lumber, Christmas trees in season — generate significant outbound volume. Mountain passes on I-84 east and on US-26 west of Mt. Hood are winter operational variables. Oregon has no general sales tax but a high graduated state income tax. Cost of living in Portland is high; rural OR is more affordable.
Related guides
- Best trucking companies in Bend, Oregon
- CDL driver salary in Bend, Oregon
- Best owner-operator companies in Oregon
The methodology behind the rankings
Pay carriers against each other within the same market (30%). Layer a weighted FMCSA SAFER safety percentile on top (25%). Score the benefits package against what actually matters for the hiring type — W2 health/financial benefits or owner-op operational perks (25%). Finish with operational performance: responsiveness to driver applications plus fleet scale (20%). All percentiles are recomputed monthly. Updated September 2026.