CDL Driver Jobs in Winchester, NY

CDL-A Company Driver - Recent Grads

Melton Truck Lines

Location: Winchester, NY
Posted: December 23, 2024

CDL-A Flatbed Driver - No Experience Required

Western Express, Inc.

Location: Winchester, NY
Posted: April 29, 2023

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

Werner Enterprises

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

Dedicated CDL-A Truck Driver - Multiple Options Available

Werner Enterprises

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

Entry Level CDL-A Driver - No Experience Required

Western Express, Inc.

Location: Winchester, NY
Posted: April 29, 2023

East Coast Regional CDL-A Driver

Western Express, Inc.

Location: Winchester, NY
Posted: August 11, 2023

CDL-A Student Driver

TMC

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

CDL-A Driver - Dry Van

Crete Carrier Corporation

Location: Winchester, NY
Posted: February 21, 2024

Dedicated Regional CDL-A Drivers - East

C.R. England

Location: Winchester, NY
Posted: February 21, 2024

Dedicated CDL-A Solo & Team Driver

Werner Enterprises

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

CDL-A OTR Truck Recovery Drivers - 48 States

C.R. England

Location: Winchester, NY
Posted: February 14, 2025

CDL-A Driver Leader

Werner Enterprises

Location: Winchester, NY
Posted: September 5, 2025

Dedicated CDL-A Dry Van Driver

Werner Enterprises

Location: Winchester, NY
Posted: February 4, 2026

CDL-A Solo OTR Truck Driver

U.S. Xpress

Location: Winchester, NY
Posted: June 18, 2026

OTR CDL-A Truck Driver

Barr-Nunn Transportation

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

CDL-A Driver Leaders

Werner Enterprises

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

CDL-A Van Solo Elite Drivers

Werner Enterprises

Location: Winchester, NY
Posted: August 13, 2026

CDL-A Company Driver - Multiple Routes

Werner Enterprises

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

CDL-A Company Truck Driver - Regional

Bolus Freight Systems, Inc.

Location: Winchester, NY
Posted: November 1, 2023

CDL-A Driver - Dry Van

Western Express, Inc.

Location: Winchester, NY
Posted: April 29, 2023

CDL-A Company Truck Driver - National

Shaffer Trucking

Location: Winchester, NY
Posted: April 29, 2023

CDL-A Driver - Zanesville, OH Fresh

Dollar General Fleet

Location: Winchester, NY
Posted: October 2, 2026

Dedicated Regional CDL-A Driver - Northeast Regional

C.R. England

Location: Winchester, NY
Posted: October 2, 2026

CDL-A Team Driver - Driver Match

Werner Enterprises

Location: Winchester, NY
Posted: September 30, 2025

CDL-A Team Truck Driver - Driver Match Program

Werner Enterprises

Location: Winchester, NY
Posted: December 30, 2025

OTR CDL-A Drivers

U.S. Xpress

Location: Winchester, NY
Posted: July 24, 2026

CDL-A Company Driver - National

Shaffer Trucking

Location: Winchester, NY
Posted: April 29, 2023

Lease Purchase

R.E. Garrison Trucking

Location: Winchester, NY
Posted: July 20, 2026

Dedicated Local CDL-A Driver

C.R. England

Location: Winchester, NY
Posted: May 4, 2023

Experienced Flatbed Driver

TMC

Location: Winchester, NY
Posted: July 25, 2023

Team OTR CDL-A Truck Drivers

Heartland Express

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

OTR CDL-A Truck Drivers

Heartland Express

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

OTR CDL-A Truck Drivers - Eastern Regional

Heartland Express

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

Dedicated CDL-A Company Driver

USA Truck

Location: Winchester, NY
Posted: September 16, 2026

Owner Operator - Solo & Team

TForce Freight

Location: Winchester, NY
Posted: September 22, 2026

Owner Operator - Solo & Team Drivers

TForce Freight

Location: Winchester, NY
Posted: September 22, 2026

CDL-A OTR Driver - National

Crete Carrier Corporation

Location: Winchester, NY
Posted: April 29, 2023

Dedicated CDL-A Truck Driver

Werner Enterprises

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

Local Dedicated CDL-A Truck Drivers - General

C.R. England

Location: Winchester, NY
Posted: July 27, 2023

CDL-A & B OTR Team Driver

Expediter Services

Location: Winchester, NY
Posted: August 29, 2023

Experienced CDL-A Truck Drivers

Western Express, Inc.

Location: Winchester, NY
Posted: April 3, 2025

CDL-A Dry Van Truck Driver

J&R Schugel

Location: Winchester, NY
Posted: February 1, 2026

OTR CDL-A Truck Driver - 12 Days Out

Crete Carrier Corporation

Location: Winchester, NY
Posted: February 10, 2026

CDL-A Solo Company Truck Driver

Barr-Nunn Transportation

Location: Winchester, NY
Pay: $85,000 – $114,000 a year
Posted: June 10, 2026

Dedicated CDL-A Company Drivers

USA Truck

Location: Winchester, NY
Posted: September 16, 2026

CDL-A Team Company Drivers

USA Truck

Location: Winchester, NY
Posted: September 16, 2026

CDL-A Owner Operators & Lease Purchase Drivers

USA Truck

Location: Winchester, NY
Posted: September 16, 2026

OTR & Regional CDL-A Driver

USA Truck

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

OTR & Regional CDL-A Drivers

USA Truck

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

CDL-A Solo OTR Truck Driver - Northeast

U.S. Xpress

Location: Winchester, NY
Posted: September 3, 2026

OTR CDL-A Flatbed Drivers

E.W. Wylie

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

OTR CDL-A Flatbed Truck Driver

Koch Trucking

Location: Winchester, NY
Posted: October 22, 2026

CDL-A Company Driver - Home Daily

J.B. Hunt

Location: Winchester, NY
Pay: $56,000 – $95,000 a year
Posted: April 29, 2023

CDL-A Team Driver - No Experience Required

Western Express, Inc.

Location: Winchester, NY
Posted: February 1, 2024

CDL-A OTR Company Driver - National

Crete Carrier Corporation

Location: Winchester, NY
Posted: April 29, 2023

CDL-A Driver - Recent Graduate

TMC

Location: Winchester, NY
Posted: July 25, 2023

OTR CDL-A Driver

Millis Transfer

Location: Winchester, NY
Posted: May 1, 2026

CDL-A Owner Operator & Independent Contractor

Expediter Services

Location: Winchester, NY
Posted: March 16, 2026

CDL-A Driver - No Experience Required

Western Express, Inc.

Location: Winchester, NY
Posted: July 14, 2026

Flatbed CDL-A Company Driver & Lease Operator

Anderson Trucking Service

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

Regional CDL-A Drivers

Hogan Transports

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

Experienced CDL-A Truck Driver

C.R. England

Location: Winchester, NY
Posted: October 23, 2026

Experienced Dedicated CDL-A Truck Driver - Earn Big

C.R. England

Location: Winchester, NY
Posted: October 23, 2026

Dedicated CDL-A Truck Driver

C.R. England

Location: Winchester, NY
Posted: October 27, 2026

CDL-A Company Driver - Home Weekly

Roehl Transport

Location: Winchester, NY
Pay: $1,482 – $2,484 a week
Posted: April 29, 2023

Student Drivers

Millis Transfer

Location: Winchester, NY
Posted: May 1, 2026

Dedicated CDL-A Truck Driver

C.R. England

Location: Winchester, NY
Posted: April 30, 2026

CDL-A Flatbed Driver

Koch Trucking

Location: Winchester, NY
Posted: October 2, 2026

CDL A & B Driver - East

Expediter Services

Location: Winchester, NY
Posted: April 1, 2026

CDL-A Flatbed Truck Driver

Western Express, Inc.

Location: Winchester, NY
Posted: April 29, 2023

CDL-A Lease Purchase Driver

Western Express, Inc.

Location: Winchester, NY
Posted: April 29, 2023

CDL-A Yard Truck Driver - Buffalo, NY

C.R. England

Location: Winchester, NY
Posted: April 29, 2023

CDL-A Team Driver - Driver Match Program Available

Werner Enterprises

Location: Winchester, NY
Posted: April 29, 2023

Student Truck Driver

TMC

Location: Winchester, NY
Posted: July 25, 2023

Entry Level Student Truck Driver

TMC

Location: Winchester, NY
Posted: July 25, 2023

CDL-A Recent Graduate

TMC

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

CDL-A Recent Graduate Truck Driver

TMC

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

Experienced CDL-A Driver

TMC

Location: Winchester, NY
Posted: July 25, 2023

Experienced Flatbed CDL-A Driver

TMC

Location: Winchester, NY
Posted: July 25, 2023

CDL-A Northeast Region Driver

Shaffer Trucking

Location: Winchester, NY
Posted: February 14, 2024

CDL-A Driver - Refrigerated

Shaffer Trucking

Location: Winchester, NY
Posted: February 21, 2024

Local Intermodal CDL-A Driver - Buffalo, NY

C.R. England

Location: Winchester, NY
Posted: March 5, 2025

Dedicated CDL-A Truck Driver - Home Daily

Werner Enterprises

Location: Winchester, NY
Posted: May 15, 2025

CDL-A OTR Open Deck Truck Driver - Nationwide

Tucker Freight Lines

Location: Winchester, NY
Posted: September 17, 2026

Regional CDL-A Driver - Michigan & Ohio

Hogan Transports

Location: Winchester, NY
Pay: $2,077 – $2,212 a week
Posted: November 26, 2025

Regional CDL-A Truck Driver - Northeast Regional

Heartland Express

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

Regional CDL-A Truck Driver - Northeast

Heartland Express

Location: Winchester, NY
Pay: $55,000 – $83,000 a year
Posted: January 2, 2026

Regional CDL-A Truck Drivers - Ohio Regional

Heartland Express

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

CDL-A Team Elite Driver

Werner Enterprises

Location: Winchester, NY
Posted: March 26, 2026

Flatbed CDL-A Company Driver

TMC

Location: Winchester, NY
Posted: July 28, 2026

CDL driver jobs in Winchester, NY