Top 592 Otr Jobs in Winchester, Ky

CDL A OTR Truck Driver - Lexington OTR Division
DSL Express —Lexington, KY
- $1,900 - $2,700 a week
- Online Application
- Dedicated
- Clean driving record
- No touch freight
- Fuel card
Quick Apply
CDL-A Regional Flatbed Truck Driver - $5,000 Sign On Bonus
Loudon County Trucking —Lexington, KY
- $1,200 - $1,600 a week
- Urgently hiring
- CDL A
- Mid-level
- Flatbed truck
- Passenger ride along program
- Dental insurance
Quick Apply
CDL-A OTR Driver - Dry Van 100% No Touch
Barr-Nunn Transportation LLC —Lexington, KY
- $0.69 - $0.75 per mile
- No touch freight
- Dry van
- CDL A
- Passenger ride along program
- Dental insurance
Quick Apply
12d
CDL-A OTR Truck Driver
Continental Express Inc. —Mount Sterling, KY
- $0.68 - $0.72 per mile
- No touch freight
- CDL A
- Mid-level
- Health insurance
- Dental insurance
Quick Apply
12d
Hazmat / Tanker Driver
Lion Freight Systems Inc —Lexington, KY
- $2,000 - $3,000 a week
- Full-time
- Hazmat Endorsement
- Dry van
- CDL A
Quick Apply
CDL A Owner Operator End Dump No Wkends
Page Transportation & Page E.T.C. —Kentucky
- $5,500 - $6,500 a week
- Owner-operator
- Hazmat Endorsement
- CDL A
Quick Apply
12d
CDL-A OTR Driver - Flatbed & Dry Van
Olympic Transport LLC —Nicholasville, KY
- $1,500 - $3,000 a week
- Full-time
- Clean driving record
- Dry van
- CDL A
- Passenger ride along program
- Fuel card
Quick Apply
CDL A Owner Operator Truck Driver
TRC Freight Inc —Kentucky
- $8,000 - $14,000 a week
- Call employer
- Clean driving record
- Owner-operator
- Dry van
- Fuel card
- Referral program
Quick Apply
5d
Entry Level Class A CDL Truck Driver
Western Express —Winchester, KY
- Up to $0.48 per mile
- Urgently hiring
- Dry van
- No experience needed
- CDL A
- Health insurance
- Dental insurance
Quick Apply
Experienced CDL A Company Drivers & Owner Operators Wanted
Raj Transport Inc. —Kentucky
- Full-time
- Owner-operator
- DOT physical examination
- Local
- Health insurance
- Dental insurance
Quick Apply
CDL Class A Owner Operators
GBA Group LLC —Kentucky
- $3,000 - $6,000 a week
- Owner-operator
- Dry van
- CDL A
- Fuel card
- Paid orientation
Quick Apply
6d
Box Truck Owner Operator OTR
ALFA FREIGHT INC —Lexington, KY
- $5,500 - $8,000 a week
- Full-time
- Owner-operator
- Mid-level
- Driver's License
- Fuel card
- Referral program
Quick Apply
CDL-A Dedicated Team Truck Driver
AAT Carriers —Lexington, KY
- $120,000 a year
- Full-time
- Hazmat Endorsement
- CDL A
- Mid-level
Quick Apply
Experienced Class A CDL Truck Driver
Western Express —Richmond, KY
- Up to $0.70 per mile
- Urgently hiring
- Dry van
- CDL A
- Mid-level
- Health insurance
- Dental insurance
Quick Apply
Class A CDL Drivers - $5000 Hiring Bonus - Top Performers +$100k |X5G|
Koch Trucking —Lexington, KY
- From $0.58 per mile
- Full-time
- Clean driving record
- Owner-operator
- CDL A
- Passenger ride along program
- Disability insurance
Quick Apply
4d
CDL A Owner Operator OTR Truck Driver
Crane Freight —Lexington, KY
- $12,000 a week
- Full-time
- Owner-operator
- Dry van
- CDL A
- Employee discount
- Fuel discount
Quick Apply
CDL A Owner Operator OTR Truck Driver
Crane Freight —Lexington, KY
- $12,000 a week
- Full-time
- Owner-operator
- Dry van
- CDL A
- Employee discount
- Fuel discount
Quick Apply
CDL-A Team Truck Driver - Dedicated Lane
Covenant Transport —Lexington, KY
- Call employer
- Dedicated
- Clean driving record
- Owner-operator
- Disability insurance
- Health insurance
Quick Apply
8d
CDL-A Team Truck Driver - Dedicated Lane
Covenant Transport —Lexington, KY
- Call employer
- Dedicated
- Clean driving record
- Owner-operator
- Disability insurance
- Health insurance
Quick Apply
8d
CDL A Team Drivers - $25,000 Sign-On
Transco Lines —Lexington, KY
- Up to $220,000 a year
- Full-time
- Hazmat Endorsement
- Dry van
- CDL A
- Passenger ride along program
- Referral program
Quick Apply
1d

I want to receive the latest job alert for otr in winchester, ky

By signing in to your account, you agree to SimplyHired's Terms of Service and consent to our Cookie and Privacy Policy.

Explore jobs in more locations

otr jobs near winchester, ky

CDL A OTR Truck Driver - Lexington OTR Division

DSL Express -
Lexington, KY

Quick Apply

Job Details

Full-time
$1,900 - $2,700 a week

Benefits

Fuel card

Qualifications

CDL A
Long-haul driving experience

Full Job Description

Our routes often begin or conclude in this region, giving local drivers reliable home time on nationwide runs doing over the road services. We are actively hiring experienced Class A CDL Solo OTR Truck Drivers for our modern fleet who live in the Lexington, KY area and surrounding communities. Lexington is a solid market for us in Kentucky with steady freight demand.

Typical Pay Highlights:

30% of line haul OR 65 a mile + bonuses (the choice most solo drivers prefer).
Average weekly gross: $1,900 – $2,400 with peaks reaching $2,700+ on legal hours.
Switch between percentage and miles pay whenever you choose.
Consistent drivers earned between $115,000 and $125,000 in 2025.
Anyone who wants to put in the effort will make good money!

Pay Details & Realistic Expectations:
Pay is performance-based. In 2025, 87% of our drivers went with the 30% percentage plan because it consistently delivered better earnings in the current market. Slow season (Q1) typically ranges from $1,900–$2,100 per week with some weeks hitting $2,400. Peak seasons (Q2 and Q4) usually run $2,100–$2,400 with some $2,700 weeks. Q3 is somewhere between. This seasonal pattern has been reliable for the past 25 years. A few exceptional top performers reached $145,000 last year driving full time.

Pay Options:

Percentage Pay (Best Option for Most Solos) - We pay up to 30% of line haul plus bonuses. We intentionally keep miles lower on percentage (2,000–2,500 in slow season and up to 3,000 in busy season) because it maximizes earnings, reduces fuel costs, and helps prevent burnout.
Miles Pay Option - Switch at any time. Up to 65 cents per mile plus bonuses based on experience and record. Typical miles: 2,500–3,600 per week.
Team Pay (Miles Only) - Up to 75¢ per mile split. Average $2,000–$2,600 per driver per week. Note: Solo percentage pay is currently the stronger choice in this market.

Apply here and get approved faster — https://www.dslfreight.com/join-our-team/.

Important Info About Our Work Ethic:
We receive a high volume of applications and are selective — we are looking for “A” stringers and true professionals. Motivated, honest, and hard-working drivers earn excellent money and are treated like family. If you prefer coasting, missing loads, or spending time at truck stops, this is not the right opportunity. We are fair, but success depends on your effort.

Still interested? Great — Here’s the link again: https://www.dslfreight.com/join-our-team/.

What Makes DSL Express Different:

We are a well-established company with 25 years in business since 2001 — large enough to offer strong support and modern equipment, yet small enough that every driver counts.
We welcome veterans and give fair-chance employment to anyone ready to work hard.
24/7 dispatch from three offices with real experienced staff.
Modern trucks (mostly automatics with some manuals available) equipped with fridges and inverters.
Company-owned mechanic shops in Chicago and Las Vegas.
Dedicated dispatchers who learn your style and preferences.
All no-touch freight in dry van or reefer trailers.
Strong carrier partnerships that combine big-company resources with a family-owned feel.

Perks:

No forced dispatch.
Ability to take the truck home during hometime with parking support.
Fuel cards and EZ-Passes provided.
Weekly direct deposit.
Flexible and reliable home time.
Dedicated lanes can be set up for consistent drivers.
Hazard occupational insurance covering lost wages, medical, and beneficiary.
Monthly bonuses for safety, delivery performance, and communication.
Extra bonuses for successful DOT inspections.

Job Description:

Class A CDL required (additional endorsements a plus).
Minimum 2+ years verifiable CDL experience.
Clean MVR and acceptable PSP report.
Dry van or reefer — all no-touch freight.
Must be comfortable with modern ELD systems and able to pass pre-employment drug screen.

Minimum Driver Qualifications:

Must be physically fit and prepared for the demands of over-the-road driving.
Valid Class A CDL with no pending suspensions.
Up-to-date valid medical card.
No failed or refused drug/alcohol tests in the last 4 years.
No DWI, DUI, or BAC convictions in the last 4 years.
No reckless driving convictions in the last 3 years.
No more than 3 moving violations or accidents in the last 3 years.
No license suspension for points or unpaid tickets in the last 3 years.
No more than 2 moving violations in the past year.
At least 3+ years of verifiable work history (including non-driving time).

We want serious, good people who take this job seriously. Apply today — https://www.dslfreight.com/join-our-team/.

About DSL Express:

WE'VE BUILT A REPUTATION ON EXCELLENCE IN SHIPPING AND LOGISTICS... DSL Express is a family-owned company with 25+ years in the Midwest, West Coast, and East Coast. We’re part of a federation of 5 companies with ~500 trucks total and 60+ years of combined experience. We have strong relationships with Chicago shippers/brokers and partners nationwide/Canada. Our experienced dispatchers (10+ years average) keep a low ratio (~5 trucks per dispatcher) so they can focus on you — flexible home time, the loads/miles you want, and support when needed. Yard parking, mechanic shops, and warehouses in Chicago + Las Vegas offices make life easier. Visit www.dslfreight.com or call 888-602-1140 x140 to learn more!

Quick Apply

Refine Your Search

otr jobs in winchester, ky

CDL A OTR Truck Driver - Lexington OTR Division

CDL-A Regional Flatbed Truck Driver - $5,000 Sign On Bonus

CDL-A OTR Driver - Dry Van 100% No Touch

CDL-A OTR Truck Driver

Hazmat / Tanker Driver

CDL A Owner Operator End Dump No Wkends

CDL-A OTR Driver - Flatbed & Dry Van

CDL A Owner Operator Truck Driver

Entry Level Class A CDL Truck Driver

Experienced CDL A Company Drivers & Owner Operators Wanted

CDL Class A Owner Operators

Box Truck Owner Operator OTR

CDL-A Dedicated Team Truck Driver

Experienced Class A CDL Truck Driver

Class A CDL Drivers - $5000 Hiring Bonus - Top Performers +$100k |X5G|

CDL A Owner Operator OTR Truck Driver

CDL A Owner Operator OTR Truck Driver

CDL-A Team Truck Driver - Dedicated Lane

CDL-A Team Truck Driver - Dedicated Lane

CDL A Team Drivers - $25,000 Sign-On

I want to receive the latest job alert for otr in winchester, ky

Related Searches

Explore jobs in more locations

Job Seeker Tools

Employer Tools

Browse

Stay Connected