Driving Jobs in Winterset, IA — Start This Week - Page 5

Driving companies hiring in Winterset, IA — 50+ open positions across CDL trucking, delivery, courier & more. Weekly pay, benefits available. Browse openings in Winterset.

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Winterset, IA

$2,275 - $4,095

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Winterset, IA

$3,080 - $5,280

Last updated: March 20, 2026