Trucking Companies in Winona, MO
Winona, MO has 9 registered for-hire trucking companies as of May 2026, making it one of Missouri's largest carrier markets by operating authority count. This figure includes active, inactive, and revoked authorities tracked by the Federal Motor Carrier Safety Administration (FMCSA).
Source: FMCSA operating authority and compliance records. Truck Graph analysis. View methodology
Fleet size and equipment distribution
9 carriers broken down by power-unit count and operation type in Winona, MO.
Fleet size distribution
By registered power-unit count. Source: FMCSA carrier census. View methodology
Operation type breakdown
Classification by carrier operation type and hazmat endorsement status. View methodology
About the Winona, MO freight market
Winona, MO is home to 9 registered for-hire motor carriers, of which 9 (100.0%) hold active operating authority as of May 2026. According to FMCSA records, the average fleet size among Winona carriers is 5.2 power units, reflecting a market dominated by owner-operators and small fleets. The Winona carrier population contributes to Missouri's broader freight economy, which the Bureau of Labor Statistics ranks among the nation's largest by trucking employment.
The fleet composition in Winona shows 11 single-truck operators (122.2% of all carriers) alongside 0 carriers operating fleets of 101+ power units. Other operations represent the largest segment with 22 carriers. This distribution is consistent with FMCSA's national pattern where approximately 91% of registered carriers operate fewer than 6 power units (FMCSA Industry Snapshot, 2024).
Authority tenure data reveals 0 carriers received new operating authority in the past 6 months, while 10 carriers have maintained continuous authority for 20+ years. New entrants face elevated scrutiny under FMCSA's New Entrant Safety Assurance Program, which mandates an 18-month monitoring period including at least one safety audit. The presence of 0 carriers with prior revocations on record underscores the importance of verifying authority status before tendering freight — a carrier's historical compliance record is publicly available through the FMCSA SAFER System.
Truck Graph identifies 0 active risk indicators among Winona carriers (0.00% of the population), flagged through cross-referencing authority history, insurance filing patterns, and known chameleon carrier behaviors. The FMCSA defines chameleon carriers as entities that "successively obtain and relinquish operating authority to evade enforcement actions." Shippers and brokers should verify carrier authority, insurance coverage, and safety ratings before every load tender — Truck Graph's Risk Check tool provides instant verification against all available compliance data.
Sources: FMCSA.dot.gov, BLS Trucking Industry Data, FMCSA SAFER System. Data verified as of .
Authority age distribution
Years since initial FMCSA authority grant date. View methodology
Risk and compliance overview
Risk indicators and fleet composition across 9 Winona carriers.
Fleet size vs carrier count
Carrier population by fleet tier. Source: FMCSA census data. View methodology
Equipment type share
Based on operation type classification and endorsements. View methodology
Largest carriers in Winona, MO
Ranked by fleet size (power units). Top 3 featured. Showing 9 of 9 total carriers.
Osburn Trucking LLC has operated for 4.5y with 15 power units and 19 drivers under Common authority.
Gateway Forest Transport LLC has operated for 4.3y with 9 power units and 6 drivers under Common authority.
Jvanwinkle Trucking LLC has operated for 9.7y with 6 power units and 6 drivers under Common authority.
Sartin'S Automotive & Towing has operated for 6.9y with 6 power units and 4 drivers under Carrier authority.
Bland Trucking LLC has operated for 24.0y with 4 power units and 4 drivers under Common authority.
Dilly Dally Trucking LLC has operated for 22.2y with 3 power units and 3 drivers under Common authority.
Michael Voyles has operated for 29.3y with 2 power units and 3 drivers under Carrier authority.
Heathen Haulin LLC has operated for 0.9y with 1 power units and 1 drivers under Common authority.
Jos Trucking LLC has operated for 3.7y with 1 power units and 1 drivers under Common authority.
All Winona carriers — complete directory
9 carriers total. Page 1 of 1. Sorted by fleet size descending.
| # | Carrier | MC # | DOT # | Fleet | Auth. age | Type | Safety | Status |
|---|---|---|---|---|---|---|---|---|
| 01 | Osburn Trucking LLC Winona, MO | MC1352990 | 3780305 | 15 | 4.5y | Dry van | 99 | Active |
| 02 | Gateway Forest Transport LLC Winona, MO | MC1410475 | 3814783 | 9 | 4.3y | Dry van | 95 | Active |
| 03 | Jvanwinkle Trucking LLC Winona, MO | MC988064 | 2927425 | 6 | 9.7y | Dry van | 95 | Active |
| 04 | Sartin'S Automotive & Towing Winona, MO | - | 3312584 | 6 | 6.9y | Dry van | 95 | Active |
| 05 | Bland Trucking LLC Winona, MO | MC535371 | 1034771 | 4 | 24.0y | Dry van | 95 | Active |
| 06 | Dilly Dally Trucking LLC Winona, MO | MC492143 | 1224884 | 3 | 22.2y | Dry van | 95 | Active |
| 07 | Michael Voyles Winona, MO | - | 675555 | 2 | 29.3y | Dry van | 95 | Active |
| 08 | Heathen Haulin LLC Winona, MO | MC1746734 | 4437166 | 1 | 0.9y | Dry van | 95 | Active |
| 09 | Jos Trucking LLC Winona, MO | MC1478268 | 3962600 | 1 | 3.7y | Dry van | 95 | Active |
Truck Graph carrier directory. Data from FMCSA operating authority records. View methodology
Find Winona carriers by equipment type
Browse specialized carriers operating in Winona, MO by trailer and equipment classification.
Explore the Missouri carrier directory
Winona is one of the top freight markets in Missouri. Browse the full Missouri trucking company directory to find carriers across all cities, or return to the national carrier index to compare states.
Nearby freight markets in Missouri
Winona trucking questions
Answers verified against FMCSA records.
How many trucking companies are in Winona, Missouri?
Winona, MO has 9 registered for-hire motor carriers as of May 2026. Of these, 9 hold active operating authority from the FMCSA.
What is the average fleet size in Winona?
The average fleet size among Winona carriers is 5.2 power units. Approximately 11 carriers operate a single truck, while 0 operate fleets of 101+ units.
How many Winona carriers have risk indicators?
Truck Graph identifies 0 active risk indicators among Winona-based carriers. These indicators are derived from authority history patterns, insurance filing anomalies, and known chameleon carrier behaviors.
How do I verify a Winona trucking company?
Use Truck Graph's DOT Lookup tool to instantly verify any carrier's authority status, insurance coverage, and safety record. You can also check the FMCSA SAFER System directly at safer.fmcsa.dot.gov.
What types of trucking companies operate in Winona?
Winona's carrier population includes other, dry van / mixed operations. The market serves general freight, specialized, and regional distribution needs.
Is Truck Graph data reliable?
Truck Graph compiles data from FMCSA authority records, insurance filings, inspection histories, and crash reports. Data refreshes continuously from verified federal sources. All 9 Winona carriers are cross-referenced against multiple compliance databases.
For journalists and researchers
Truck Graph data is open and citable. For press inquiries, contact our editorial team.