Trucking Companies in Winchester, KY

Winchester, KY is home to 50 registered for-hire motor carriers, of which 50 (100.0%) hold active operating authority as of May 2026. According to FMCSA records, the average fleet size among Winchester carriers is 6.4 power units, reflecting a market dominated by owner-operators and small fleets. The Winchester carrier population contributes to Kentucky's broader freight economy, which the Bureau of Labor Statistics ranks among the nation's largest by trucking employment.

The fleet composition in Winchester shows 224 single-truck operators (448.0% of all carriers) alongside 1 carriers operating fleets of 101+ power units. Other operations represent the largest segment with 399 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 8 carriers received new operating authority in the past 6 months, while 139 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 Winchester 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 May 31, 2026 at 1:42 PM.

Authority age distribution

Years since initial FMCSA authority grant date. View methodology

How many trucking companies are in Winchester, Kentucky?

Winchester, KY has 50 registered for-hire motor carriers as of May 2026. Of these, 50 hold active operating authority from the FMCSA.

What is the average fleet size in Winchester?

The average fleet size among Winchester carriers is 6.4 power units. Approximately 224 carriers operate a single truck, while 1 operate fleets of 101+ units.

How many Winchester carriers have risk indicators?

Truck Graph identifies 0 active risk indicators among Winchester-based carriers. These indicators are derived from authority history patterns, insurance filing anomalies, and known chameleon carrier behaviors.

How do I verify a Winchester 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 Winchester?

Winchester'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 50 Winchester carriers are cross-referenced against multiple compliance databases.