Driving Jobs in Winchester, KY — See Openings

As of May 2026, there are 160+ open driving positions in Winchester, KY. Current pay ranges from $14 to $155,250 per year. Top hiring areas include Delivery Driver, Cdl Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

Coach USA

Charter Bus Driver-CDL B With Passenger Endorsement-Winchester,KY

Winchester, KY

$20 - $29

Granite Construction

Winchester,KY:CDL B Water Truck Driver-Construction Site Dust Control

Winchester, KY

$26 - $32

Corporate Catering Couriers

Corporate Catering Couriers is hiring a Independent Contractor

Winchester, ID

$3,500 - $6,000

Express Logistics

Winchester Full-time Opening:Delivery Driver-Full Time Local Routes

Winchester, KY

$19 - $24

DoorDash

Doordash Needs Flower Delivery Driver in Winchester | Hiring

Winchester, IL

$2,640 - $4,620

Clean Harbors

Clean Harbors is hiring a CDL B Vacuum Truck Driver-Industrial

Winchester, KY

$26 - $35

GoPuff

Apply Now:Convenience Store Delivery Driver in Winchester | Hiring

Winchester, KY

$2,548 - $4,095

DoorDash

Apply Now in Winchester:Delivery Driver-Food Delivery Part Time

Winchester, ID

$15 - $22

Instacart

Winchester Pet Supply Delivery Driver with $2.9k-$4.8k/Month Pay

Winchester, KY

$2,900 - $4,800

Roadie

Big & Bulky Delivery Driver Needed-Winchester Area | Hiring

Winchester, KY

$4,200 - $7,200

GoPuff

Join Gopuff in Winchester as a Convenience Store Delivery Driver

Winchester, ID

$2,464 - $3,960

Wayfair

Winchester,KY:Delivery Driver-Furniture And Appliance Home

Winchester, KY

$21 - $27

Driving Jobs in Winchester — FAQ

How many driving jobs are available in Winchester, KY right now?
There are currently 160+ open driving positions in Winchester, KY. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Winchester?
Driving job pay in Winchester varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Winchester?
Yes. Many delivery driver, courier, and DSP positions in Winchester require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Winchester?
Driving jobs in Winchester offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Winchester?
Benefits vary by employer, but many driving positions in Winchester offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Winchester?
Your take-home pay as a driver in Winchester depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Winchester?
Yes, many driving positions in Winchester are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 160+ listings above and apply directly.

Last updated: May 13, 2026