CDL Driver Jobs in Winchester, KY

CDL-A Company Driver - Recent Grads

Melton Truck Lines

Location: Winchester, KY
Posted: December 23, 2024

CDL-A Company Driver - Solos, Teams, and Leaders

Werner Enterprises

Location: Winchester, KY
Pay: $120,000 – $125,000 a year
Posted: April 29, 2023

Dedicated CDL-A Truck Driver - Multiple Options Available

Werner Enterprises

Location: Winchester, KY
Pay: $120,000 – $125,000 a year
Posted: April 29, 2023

Regional CDL-A Truck Driver - Shelbyville, KY

Ryder

Location: Winchester, KY
Posted: October 9, 2026

Entry Level CDL-A Driver - No Experience Required

Western Express, Inc.

Location: Winchester, KY
Posted: April 29, 2023

CDL-A Driver - Bowling Green, KY Fresh

Dollar General Fleet

Location: Winchester, KY
Posted: June 5, 2026

CDL-A Student Driver

TMC

Location: Winchester, KY
Pay: $500 a week
Posted: July 25, 2023

CDL-A Company Truck Driver

J&R Schugel

Location: Winchester, KY
Posted: January 8, 2024

CDL-A Driver - Dry Van

Crete Carrier Corporation

Location: Winchester, KY
Posted: February 21, 2024

Dedicated Regional CDL-A Drivers - East

C.R. England

Location: Winchester, KY
Posted: February 21, 2024

Dedicated CDL-A Solo & Team Driver

Werner Enterprises

Location: Winchester, KY
Pay: $120,000 – $125,000 a year
Posted: September 30, 2024

CDL-A Driver Leader

Werner Enterprises

Location: Winchester, KY
Posted: September 5, 2025

CDL-A OTR Company Truck Driver - Dry Van

Tucker Freight Lines

Location: Winchester, KY
Posted: October 10, 2025

CDL-A OTR Company Truck Driver - Open Deck

Tucker Freight Lines

Location: Winchester, KY
Posted: October 10, 2025

CDL-A Reefer Owner Operators

APL Cargo, Inc.

Location: Winchester, KY
Posted: November 1, 2025

Dedicated CDL-A Dry Van Driver

Werner Enterprises

Location: Winchester, KY
Posted: February 4, 2026

CDL-A Solo OTR Truck Driver

U.S. Xpress

Location: Winchester, KY
Posted: June 18, 2026

OTR CDL-A Truck Driver

Barr-Nunn Transportation

Location: Winchester, KY
Pay: $90,000 – $114,000 a year
Posted: March 30, 2026

CDL-A Driver Leaders

Werner Enterprises

Location: Winchester, KY
Pay: $1,500 a week
Posted: July 6, 2026

CDL-A Van Solo Elite Drivers

Werner Enterprises

Location: Winchester, KY
Posted: August 13, 2026

CDL-A Independent Contractors

IWX Motor Freight

Location: Winchester, KY
Posted: July 31, 2026

CDL-A Independent Contractor

IWX Motor Freight

Location: Winchester, KY
Posted: July 31, 2026

CDL-A Independent Contractor

IWX Motor Freight

Location: Winchester, KY
Posted: July 31, 2026

CDL-A Truck Driver - Virtual Hiring Event

Hogan Transports

Location: Winchester, KY
Posted: November 2, 2026

CDL-A Company Driver - Multiple Routes

Werner Enterprises

Location: Winchester, KY
Pay: $120,000 – $125,000 a year
Posted: April 29, 2023

CDL-A Driver - Dry Van

Western Express, Inc.

Location: Winchester, KY
Posted: April 29, 2023

CDL-A Company Truck Driver - National

Shaffer Trucking

Location: Winchester, KY
Posted: April 29, 2023

CDL-A Driver - Multiple Options Available

Hogan Transports

Location: Winchester, KY
Posted: April 29, 2023

CDL-A Truck Driver - Dollar Tree South Carolina

C.R. England

Location: Winchester, KY
Pay: $1,400 a week
Posted: May 2, 2023

Dedicated Regional CDL-A Driver - Southeast Regional

C.R. England

Location: Winchester, KY
Posted: October 2, 2026

OTR Team CDL-A Company Truck Drivers

Transco Lines

Location: Winchester, KY
Posted: May 14, 2026

CDL-A Company Flatbed Driver

Pioneer

Location: Winchester, KY
Posted: September 3, 2025

CDL-A Team Driver - Driver Match

Werner Enterprises

Location: Winchester, KY
Posted: September 30, 2025

CDL-A Team Truck Driver - Driver Match Program

Werner Enterprises

Location: Winchester, KY
Posted: December 30, 2025

Dedicated CDL-A Company Truck Driver

U.S. Xpress

Location: Winchester, KY
Posted: June 18, 2026

CDL-A Flatbed Truck Drivers

System Transport

Location: Winchester, KY
Pay: $52,968.74 – $130,117.87 a year
Posted: June 23, 2026

CDL-A OTR Truck Driver - Dry Van

Rock Solid Logistics

Location: Winchester, KY
Posted: October 8, 2026

OTR CDL-A Drivers

U.S. Xpress

Location: Winchester, KY
Posted: July 24, 2026

Dedicated CDL-A Driver

U.S. Xpress

Location: Winchester, KY
Posted: July 24, 2026

Regional CDL-A Truck Driver

U.S. Xpress

Location: Winchester, KY
Posted: September 22, 2026

CDL-A OTR Company Truck Drivers - Dry Van

Tucker Freight Lines

Location: Winchester, KY
Posted: October 5, 2026

CDL-A Company Driver - National

Shaffer Trucking

Location: Winchester, KY
Posted: April 29, 2023

Lease Purchase

R.E. Garrison Trucking

Location: Winchester, KY
Posted: July 20, 2026

Experienced Flatbed Driver

TMC

Location: Winchester, KY
Posted: July 25, 2023

CDL-A OTR Driver

Hunt Transportation

Location: Winchester, KY
Posted: October 2, 2023

CDL-A Truck Driver

Dollar General Fleet

Location: Winchester, KY
Posted: June 4, 2026

Dedicated Regional CDL-A Driver - Dollar Tree South Carolina

C.R. England

Location: Winchester, KY
Pay: $1,400 a week
Posted: January 20, 2026

Regional CDL-A Truck Drivers - Southeast Regional

Heartland Express

Location: Winchester, KY
Pay: $53,000 – $83,000 a year
Posted: January 2, 2026

Team OTR CDL-A Truck Drivers

Heartland Express

Location: Winchester, KY
Pay: $65,000 – $97,000 a year
Posted: January 2, 2026

OTR CDL-A Truck Drivers

Heartland Express

Location: Winchester, KY
Pay: $60,000 – $95,000 a year
Posted: January 2, 2026

OTR CDL-A Truck Drivers - Eastern Regional

Heartland Express

Location: Winchester, KY
Pay: $60,000 – $99,000 a year
Posted: January 2, 2026

Regional CDL-A Truck Driver - Southcentral Regional

Heartland Express

Location: Winchester, KY
Pay: $52,000 – $84,000 a year
Posted: January 2, 2026

CDL-A Team Truck Driver

Transco Lines

Location: Winchester, KY
Posted: May 5, 2026

CDL-A OTR Refrigerated Company Driver

Navajo Express

Location: Winchester, KY
Posted: August 4, 2026

Dedicated CDL-A Drivers - Winchester, KY

Hogan Transports

Location: Winchester, KY
Pay: $81,000 – $85,000 a year
Posted: August 18, 2026

Dedicated CDL-A Company Driver

USA Truck

Location: Winchester, KY
Posted: September 16, 2026

Owner Operator - Solo & Team

TForce Freight

Location: Winchester, KY
Posted: September 22, 2026

Owner Operator - Solo & Team Drivers

TForce Freight

Location: Winchester, KY
Posted: September 22, 2026

Owner Operator - Solo & Team CDL-A Drivers

TForce Freight

Location: Winchester, KY
Posted: November 3, 2026

CDL-A OTR Driver - National

Crete Carrier Corporation

Location: Winchester, KY
Posted: April 29, 2023

Dedicated CDL-A Truck Driver

Werner Enterprises

Location: Winchester, KY
Pay: $120,000 – $125,000 a year
Posted: April 29, 2023

CDL-A Extended Regional Driver

Service Transportation

Location: Winchester, KY
Pay: $85,000 – $100,000 a year
Posted: December 9, 2025

CDL-A & B OTR Team Driver

Expediter Services

Location: Winchester, KY
Posted: August 29, 2023

Experienced CDL-A Truck Drivers

Western Express, Inc.

Location: Winchester, KY
Posted: April 3, 2025

CDL-A Flatbed Company Driver

Pioneer

Location: Winchester, KY
Posted: August 28, 2025

CDL-A Dry Van Truck Driver

J&R Schugel

Location: Winchester, KY
Posted: February 1, 2026

OTR CDL-A Truck Driver - 12 Days Out

Crete Carrier Corporation

Location: Winchester, KY
Posted: February 10, 2026

Dedicated CDL-A Company Drivers

USA Truck

Location: Winchester, KY
Posted: September 16, 2026

CDL-A Team Company Drivers

USA Truck

Location: Winchester, KY
Posted: September 16, 2026

CDL-A Owner Operators & Lease Purchase Drivers

USA Truck

Location: Winchester, KY
Posted: September 16, 2026

OTR & Regional CDL-A Driver

USA Truck

Location: Winchester, KY
Pay: $1,200 – $1,700 a week
Posted: September 16, 2026

OTR & Regional CDL-A Drivers

USA Truck

Location: Winchester, KY
Pay: $1,200 – $1,700 a week
Posted: September 16, 2026

CDL-A Solo OTR Truck Driver - Midwest

U.S. Xpress

Location: Winchester, KY
Posted: September 3, 2026

CDL-A Solo and Team Driver

Paschall Truck Lines

Location: Winchester, KY
Posted: April 29, 2023

CDL-A Team Driver - No Experience Required

Western Express, Inc.

Location: Winchester, KY
Posted: February 1, 2024

CDL-A OTR Company Driver - National

Crete Carrier Corporation

Location: Winchester, KY
Posted: April 29, 2023

CDL-A Driver - Utility Fleet

Hogan Transports

Location: Winchester, KY
Pay: $2,400 – $2,500 a week
Posted: August 26, 2026

CDL-A Driver - Recent Graduate

TMC

Location: Winchester, KY
Posted: July 25, 2023

CDL-A Driver - Midwest Regional

Paschall Truck Lines

Location: Winchester, KY
Posted: March 17, 2026

OTR CDL-A Driver

Millis Transfer

Location: Winchester, KY
Posted: May 1, 2026

CDL-A Owner Operator & Independent Contractor

Expediter Services

Location: Winchester, KY
Posted: March 16, 2026

Flatbed CDL-A Company Driver & Lease Operator

Anderson Trucking Service

Location: Winchester, KY
Pay: $1,700 – $2,400 a week
Posted: July 7, 2026

Regional CDL-A Drivers

Hogan Transports

Location: Winchester, KY
Pay: $1,635 – $2,210 a week
Posted: September 1, 2026

Dry Van CDL-A Company Driver & Lease Operator

Anderson Trucking Service

Location: Winchester, KY
Pay: $1,500 – $1,900 a week
Posted: September 9, 2026

CDL-A Regional End Dump & OTR Dry Van Drivers

Woody Bogler Trucking

Location: Winchester, KY
Posted: October 9, 2026

Regional CDL-A Company Truck Driver

Convoy Systems

Location: Winchester, KY
Pay: $75,000 – $90,000 a year
Posted: October 2, 2026

OTR CDL-A Flatbed Drivers

E.W. Wylie

Location: Winchester, KY
Pay: $1,525 – $2,010 a week
Posted: October 6, 2026

Experienced Dedicated CDL-A Truck Driver - Earn Big

C.R. England

Location: Winchester, KY
Posted: October 23, 2026

Dedicated CDL-A Truck Driver

C.R. England

Location: Winchester, KY
Posted: October 27, 2026

OTR CDL-A Drivers

Premier Transportation

Location: Winchester, KY
Posted: November 4, 2026

CDL-A OTR Company Driver

Brady Trucking

Location: Winchester, KY
Posted: November 3, 2026

CDL-A Independent Contractors

Western Flyer Xpress

Location: Winchester, KY
Posted: November 5, 2026

Experienced CDL-A OTR Dry Van Driver

Woody Bogler Trucking

Location: Winchester, KY
Posted: September 11, 2026

Student Drivers

Millis Transfer

Location: Winchester, KY
Posted: May 1, 2026

OTR CDL-A Truck Driver - Reefer

APL Cargo, Inc.

Location: Winchester, KY
Pay: $78,000 – $109,200 a year
Posted: March 6, 2025

OTR CDL-A Reefer Driver

APL Cargo, Inc.

Location: Winchester, KY
Posted: March 6, 2025

OTR CDL-A Flatbed Driver

Hogan Transports

Location: Winchester, KY
Pay: $1,800 – $2,307 a week
Posted: November 3, 2026

Dedicated CDL-A Truck Driver

C.R. England

Location: Winchester, KY
Posted: April 30, 2026

CDL-A Regional Company Drivers - Home Weekly

APL Cargo, Inc.

Location: Winchester, KY
Posted: June 3, 2026

Dedicated Regional CDL-A Truck Drivers - Morehead, KY

Hogan Transports

Location: Winchester, KY
Pay: $95,000 – $100,000 a year
Posted: July 14, 2026

Regional CDL-A Company Driver

Paschall Truck Lines

Location: Winchester, KY
Posted: August 27, 2026

CDL-A Lease Purchase Truck Driver

Harpers Hot Shot Trucking

Location: Winchester, KY
Posted: September 11, 2026

CDL-A Company Truck Drivers

Western Flyer Xpress

Location: Winchester, KY
Posted: November 3, 2026

CDL-A Owner Operator

Hub Group

Location: Winchester, KY
Posted: April 16, 2026

Experienced CDL-A Company Driver

Dollar General Fleet

Location: Winchester, KY
Posted: June 26, 2026

CDL-A Truck Driver Trainers

Western Express, Inc.

Location: Winchester, KY
Posted: April 3, 2025

CDL A & B Driver - East

Expediter Services

Location: Winchester, KY
Posted: April 1, 2026

CDL-A Flatbed Truck Driver

Western Express, Inc.

Location: Winchester, KY
Posted: April 29, 2023

CDL-A Lease Purchase Driver

Western Express, Inc.

Location: Winchester, KY
Posted: April 29, 2023

Regional CDL-A Driver - S.E. Region

Hogan Transports

Location: Winchester, KY
Pay: $1,650 – $1,825 a week
Posted: May 1, 2026

CDL-A Team Driver - Driver Match Program Available

Werner Enterprises

Location: Winchester, KY
Posted: April 29, 2023

Student Truck Driver

TMC

Location: Winchester, KY
Posted: July 25, 2023

Entry Level Student Truck Driver

TMC

Location: Winchester, KY
Posted: July 25, 2023

CDL-A Recent Graduate

TMC

Location: Winchester, KY
Pay: $1,350 – $1,600 a week
Posted: July 25, 2023

CDL-A Recent Graduate Truck Driver

TMC

Location: Winchester, KY
Pay: $1,350 – $1,600 a week
Posted: July 25, 2023

Experienced CDL-A Driver

TMC

Location: Winchester, KY
Posted: July 25, 2023

Experienced Flatbed CDL-A Driver

TMC

Location: Winchester, KY
Posted: July 25, 2023

CDL-A Midwest Region Driver

Crete Carrier Corporation

Location: Winchester, KY
Posted: November 16, 2023

CDL-A Driver - Refrigerated

Shaffer Trucking

Location: Winchester, KY
Posted: February 21, 2024

Regional CDL-A Driver - Midwest Region

Crete Carrier Corporation

Location: Winchester, KY
Posted: April 24, 2024

CDL-A Team Drivers

APL Cargo, Inc.

Location: Winchester, KY
Posted: April 17, 2025

CDL-A OTR Open Deck Truck Driver - Nationwide

Tucker Freight Lines

Location: Winchester, KY
Posted: September 17, 2026

Regional CDL-A Truck Driver - Northeast Regional

Heartland Express

Location: Winchester, KY
Pay: $55,000 – $93,000 a year
Posted: January 2, 2026

Regional CDL-A Truck Driver - Midwest Regional

Heartland Express

Location: Winchester, KY
Pay: $55,000 – $80,000 a year
Posted: January 2, 2026

Regional CDL-A Truck Drivers - Ohio Regional

Heartland Express

Location: Winchester, KY
Pay: $55,000 – $73,000 a year
Posted: January 2, 2026

CDL-A Truck Driver - East Coast Regional 5.5 Days

Crete Carrier Corporation

Location: Winchester, KY
Posted: September 2, 2026

Dedicated CDL-A Truck Driver - Costco Dedicated Florida

Shaffer Trucking

Location: Winchester, KY
Posted: January 27, 2026

CDL-A Driver - Costco Dedicated Route

Crete Carrier Corporation

Location: Winchester, KY
Posted: March 6, 2026

CDL-A Team Elite Driver

Werner Enterprises

Location: Winchester, KY
Posted: March 26, 2026

Regional CDL-A Truck Driver

Barr-Nunn Transportation

Location: Winchester, KY
Pay: $85,000 – $105,000 a year
Posted: March 30, 2026

CDL-A Western Regional Refrigerated Driver

Shaffer Trucking

Location: Winchester, KY
Posted: May 11, 2026

Regional CDL-A Dry Van - Western Regional

Crete Carrier Corporation

Location: Winchester, KY
Pay: $87,430 – $98,417 a year
Posted: May 11, 2026

OTR CDL-A Driver

C.R. England

Location: Winchester, KY
Posted: May 15, 2026

CDL-A Operators

Expediter Services

Location: Winchester, KY
Posted: June 10, 2026

Flatbed CDL-A Company Driver

TMC

Location: Winchester, KY
Posted: July 28, 2026

Dedicated CDL-A Driver - Ohio Tractor Supply

Crete Carrier Corporation

Location: Winchester, KY
Posted: November 6, 2026

CDL-A Lease Purchase Drivers

J&R Schugel

Location: Winchester, KY
Posted: November 3, 2026

CDL driver jobs in Winchester, KY