126 Results for

Trucker Jobs in Winchester, KY

Jobs

New!

Richmond, KYToday

$65–$75 Per Hour

With more than 35 years of expertise, our owners and executives know how to support their drivers, keep the fleet operating smoothly, and foster a culture of hard work so drivers can succeed. Free round trip flight back and forth to home for their home time for drivers residing outside our operating area.

New!

Georgetown, KY4 days ago

Full pay package also includes other accessorial compensation to include tarp pay, stop pay, detention pay, border crossing pay, safety bonuses, and over-dimensional pay as appropriate. See Advantage AI Privacy Policy at https://www.advantage.ai/legal/privacy-policy and SonicJobs Privacy Policy at https://www.sonicjobs.com/us/privacy-policy and Terms of Use at https://www.sonicjobs.com/us/terms-conditions.

New!

Richmond, KY3 days ago

$1,350–$1,600 Per Week

Our Experienced Driver Orientation Program keeps you separated from newbies and is only 3-5 days long, depending upon your experience levelIf you have limited or no flatbed experience, we will allow you to ride with a Driver Trainer to learn the ropes of flatbedding. Percentage pay is loved by Experienced drivers because it pays more than traditional per-mile programs, and they get a share of the gain every time TMC gets a rate increase from our customers.

New!

Georgetown, KY4 days ago

Full pay package also includes other accessorial compensation to include tarp pay, stop pay, detention pay, border crossing pay, safety bonuses, and over-dimensional pay as appropriate. That's right Recent CDL-A graduates—qualified applicants with a valid CDL-A license may have the opportunity to receive training and start their driving career with us during this special period and special offer, only valid through May 31, 2026.

Lexington, KY8 days ago

Pass a Ryder Background and Motor vehicle check including drug and alcohol verification from previous employers for the last 3 years. Ryder is a commercial transportation, logistics, and supply chain management solutions company in business for over 80 years.

New!

Lexington, KY1 day ago

Enjoy 99% no-touch freight, competitive accessorial pay, strong Hazmat pay, and bonuses-including a $2,000 maintenance bonus* for new contractors, the Dart Diamond Rewards annual bonus and a $3,000 referral bonus.*. Pick steady miles and stability, ride high as your own boss, or step into truck ownership with programs designed to reduce risk and increase earning power.

New!

Richmond, KY2 days ago

$90,000–$100,000 Per Year

Werner's Career Track Program allows drivers to focus on the enhancement of their skills by getting valuable, hands-on experience with one of our highly skilled Leader Drivers. Whether you’re a seasoned veteran with a knack for hauling refrigerated freight or just starting your career, we have truck-driving jobs available to fit all levels of experience.

New!

Lexington-Fayette, KY3 days ago

$1,200–$1,500 Per Week

Mesilla Valley Transportation (MVT) is looking for truck drivers that are passionate about being on the road and understand that safety and delivering on time are critical. Must live within highlighted markets in Texas and New Mexico or within:50 miles of Salt Lake City.

New!

Richmond, KY4 days ago

$85,000–$105,000 Per Year

Barr-Nunn's exceptional safety record, combined with our award-winning on-time service, gives us the ability to efficiently meet the needs of top-notch shippers and has made Barr-Nunn a stable and profitable operation. Higher band pay per mile on complete loads less than 400 miles0 - 100 miles earn $35 per load.

New!

Lexington, KY6 days ago

$52,000–$84,000 Per Year

Latest Kenworth, Freightliner, & International tractorsWe buy new and keep it while under warrantee to have better uptime for you to keep rolling. Newly updated and remodeled coast-to-coast terminal facilitiesFree showers.

New!

Lexington-Fayette, KY3 days ago

$1,200–$1,500 Per Week

New!

Richmond, KY2 days ago

$55–$57 Per Week

Founded in 1974, Indian River Transport provides reliable, competitive interstate, intrastate, and international transportation of bulk food-grade commodities. As a leader in bulk liquid food-grade tank carriers, Indian River Transport sets the tone for the rest of our industry.

New!

Lexington, KY1 day ago

$800–$900 Per Week

Fixed, discounted fuel rate: Hirschbach drivers pay $.99/gallon for fuel, regardless of price at pump. We offer drivers industry-leading 24/7 support and our ultra-modern truck fleet comes with the latest features and technology.

New!

Richmond, KY4 days ago

$0.59–$0.63 Per Year

We offer truckload, dedicated, and intermodal services throughout the eastern United States, with terminals located in Tennessee, Missouri, North Carolina, and Kentucky. Ozark Motor Lines, Inc. partners with drivers across the Mid-South to keep vital supply chains moving.

New!

Nicholasville, KY4 days ago

Delivery locations: California, Arizona, New Mexico, Oklahoma, Texas, Missouri, Arkansas, Louisiana, Illinois, Indiana, Michigan, Ohio, Kentucky, Tennessee, Mississippi, Alabama, Georgia, North Carolina, South Carolina, and Florida. See Advantage AI Privacy Policy at https://www.advantage.ai/legal/privacy-policy and SonicJobs Privacy Policy at https://www.sonicjobs.com/us/privacy-policy and Terms of Use at https://www.sonicjobs.com/us/terms-conditions.

New!

Lexington, KY2 days ago

$65,000–$75,000

The CDL-A Driver is responsible for driving a tractor trailer or straight truck on intrastate and interstate local, over-the-road (OTR), shuttle, and overnight and drive and drop routes for the purpose of delivering and/or unloading food and food related products to customers in a safe and timely manner and in accordance with Department of Transportation (DOT) regulations. Performance Foodservice, PFG’s broadline distributor, maintains a unique relationship with a variety of local customers, including independent restaurants and hotels, healthcare facilities, schools, and quick-service eateries.

New!

Lexington, KY1 day ago

$1,400–$2,200 Per Week

Now under new management, Boyd is focused on what drivers want most: more home time, better planning, and expanded running lanes. Top drivers earn up to $90,000 per year, with a $1,200 weekly minimum when running 1,800+ miles.

New!

Lexington, KY1 day ago

$1,500–$1,800 Per Week

And it's not just our opinion - in a recent survey of flatbed drivers, nearly 90% confirmed that P&S pays better than other flatbed trucking companies and is better to work for. We hire experienced flatbed drivers and treat them like family, providing higher support, better pay and utmost respect - and clean, comfortable trucks!

Richmond, KY16 days ago

$0.45–$0.65 Per Hour

Our support, strong freight base, and routes are all designed to give contractors every opportunity the open road has to offer. Oklahoma City terminal is centrally located on I-40 for easy access from the lower 48 states.

New!

Richmond, KY4 days ago

$60,000–$99,000 Per Year

Earn $60,000-$99,000 per year - average is $72,000 per yearEarn an additional 5 CPM paid for all miles driven north of MD and east of I-81. Latest Kenworth, Freightliner, & International tractorsWe buy new and keep it while under warrantee to have better uptime for you to keep rolling.

Richmond, KY10 days ago

$4,450–$5,600 Per Week

At Anderson Trucking Service (ATS), our OTR Dry Van Lease Operator program gives you access to quality freight, newer equipment, and full backing from a trusted carrier. Cloud, Minnesota, ATS has built a reputation for supporting drivers, providing reliable freight, and maintaining newer equipment.

New!

Lexington, KY1 day ago

We focus on consistency, communication, and respect, building long-term relationships with drivers who want steady pay, reliable home time, and a company that puts people first. High levels of contracted freight with award-winning shippers, paid miles both empty and loaded while on duty, and fewer drivers per dispatcher for better communication.

New!

Lexington, KY1 day ago

$1,400–$1,600

We know drivers are the backbone of our success, and we work hard to create a safe, supportive environment where your experience is valued and your performance is rewarded. Strong earnings averaging $1,400-$1,600, with 60-61CPM base pay, plus safety and performance incentives built in.*.

New!

Lexington, KY1 day ago

$0.62–$0.66 Per Year

Run dedicated regional routes supporting specific distribution centers and get home weekly, giving you predictable resets without sacrificing steady miles. At Dollar General, drivers aren't just moving freight - they're supporting stores that communities rely on every day.

New!

Richmond, KY1 day ago

$0.55–$0.66 Per Hour

Run 2,200-2,500+ miles per week on steady OTR freight, staying out about two weeks at a time with planned home time built into a reliable work-rest rhythm. Average 2,200-2,500+ miles per week on consistent OTR lanes, typically running one to two weeks out with structured time off you can plan around.

Richmond, KY11 days ago

Minimum of 6 months of verifiable OTR tractor-trailer experience in the last 12 months or 12+ Months Experience in Last 2 Years. Must be 23 years of age or older (21 years if prior military).

New!

Georgetown, KY1 day ago

$60–$69 Per Week

With decades of experience and a reputation built on safety and integrity, we provide the tools, equipment, and culture to help you succeed on and off the road. All pay and bonus amounts may vary by job type, location, experience level, and performance and are subject to change based on company discretion.

New!

Richmond, KY1 day ago

$65–$72 Per Hour

New!

Richmond, KY3 days ago

$86,000–$86,000 Per Year

See Dollar General Fleet Privacy Policy at https://www.careerweb.site/disclosure-form/ and SonicJobs Privacy Policy at https://www.sonicjobs.com/us/privacy-policy and Terms of Use at https://www.sonicjobs.com/us/terms-conditions. As a driver for Dollar General's private fleet, you will be connecting our distribution centers with existing Dollar General stores and new stores opening across the country.

New!

Lexington, KY1 day ago

$90,000–$95,000 Per Year

With multiple driving opportunities, late-model equipment, and a freight network designed to keep you moving-not waiting-you can choose the path that fits your goals and grow your income your way. Run 2,500-3,000 miles per week across the Midwest, Mid-Atlantic, and Southeast-no NYC and mostly drop + hook to keep your week moving smoothly.

New!

Lexington, KY1 day ago

$60–$65 Per Hour

With multiple driving opportunities, late-model equipment, and a freight network designed to keep you moving-not waiting-you can choose the path that fits your goals and grow your income your way. Independent operators get higher earning potential and business flexibility without the heavy commitment-or financial risk-of full ownership.

New!

Lexington, KY1 day ago

$600–$700

Lease Purchase drivers average $6,000 gross per week, earning 72% of linehaul plus fuel surcharge, turning steady freight into serious weekly income. Whether you're running as a company driver or stepping into a Lease Purchase role, Suit offers respectful dispatch, predictable freight, and real support.

New!

Cynthiana, KY6 days ago

$100,000–$110,000

Our nationwide network of dedicated opportunities allows drivers the opportunity to find predictable home time, competitive pay rates, and stable customer freight that best suits their needs. Drivers can expect a career embodied by safety, teamwork, professionalism, integrity, and the constant pursuit of excellence.

New!

Richmond, KY1 day ago

$1,400–$1,650 Per Week

Lease Purchase drivers average $1,400-$1,650 in weekly take-home pay, combining mileage pay, fuel surcharge, and accessorial earnings. We focus on consistency, communication, and respect, building long-term relationships with drivers who want steady pay, reliable home time, and a company that puts people first.

New!

Richmond, KY1 day ago

New!

Georgetown, KY1 day ago

$0.45–$0.56 Per Week

As a driver-focused agency with deep experience across the transportation industry, we understand what today's professional drivers expect-and we don't make promises we can't keep. We believe drivers are the backbone of this country, and we make sure they're treated that way-credited, supported, and respected for the work they do every day.

New!

Cynthiana, KY5 days ago

Working to build more dedicated opportunities – sister company is logistics based and will help to build those opportunities as well . If working on an observed holiday - $50 on top of regular revenue .

New!

Stanton, KY6 days ago

$915–$1,120 Per Year

This diversity and openness ensures all associates have equal access to opportunities and resources to contribute fully to the organization's success, and it fuels innovation, improves strategic thinking and cultivates leadership. Company-paid CDL training options: tuition reimbursement ($200/month) or CDL Apprenticeship Training (paid five-to-six week training at a Schneider facility).

New!

Lexington, KY1 day ago

$1,600–$1,800 Per Week

We offer a full month of paid training with an experienced mentor so you can gain confidence, develop real-world skills, and begin your career with the support you need. If you are ready to start your trucking career with paid training, strong weekly pay, and reliable home time, apply today.

New!

Berea, KY3 days ago

$1,200–$1,470 Per Year

This diversity and openness ensures all associates have equal access to opportunities and resources to contribute fully to the organization's success, and it fuels innovation, improves strategic thinking and cultivates leadership. The feeling you get from keeping the customer's freight moving and contributing to the overall success of the customer will be nothing short of pride.

Lexington, KY25 days ago

$1,600–$1,800 Per Week

We provide stable W2 employment, consistent freight, modern equipment, and an operations team focused on supporting drivers as they develop safe, productive careers. With consistent freight and milage, our routes offer regular weekly home time, a good weekly pay-check and a full benefits package from day one.

Stanton, PA21 days ago

$1,500–$1,500

Currently, we have a need for drivers in various areas for a Regional truck driving positions (see below). Drivers need a safe and secure place to park truck near their home.

Lexington, KY30+ days ago

$104,000–$120,000

Join a top-paying regional dry van fleet hauling 100% no-touch freight across the Northeast and Midwest. 101–400 miles: $25/load (loaded, non-relayed only).

Lexington, KY30+ days ago

$0.40–$0.48

Western Express has immediate openings for entry level company truck drivers and driver trainers. Experienced top earners and trainers make up to $100,000 per year!

Winchester, KY30+ days ago

$0.40–$0.48

Western Express has immediate openings for entry level company truck drivers and driver trainers. Experienced top earners and trainers make up to $100,000 per year!

Georgetown, KY30+ days ago

$0.40–$0.48

Western Express has immediate openings for entry level company truck drivers and driver trainers. Experienced top earners and trainers make up to $100,000 per year!

Lexington, KY30+ days ago

$0.40–$0.63

Western Express has immediate openings in our Flatbed and Dry Van divisions for company drivers and driver trainers! NEW SAFETY BONUS - Qualify for an extra 5 CPM (van) or extra 7 CPM (flatbed) and take home up to $800 more every month!*.

Winchester, KY30+ days ago

$0.40–$0.63

Georgetown, KY30+ days ago

$0.40–$0.63

Lexington, KY30+ days ago

$1,670–$2,020 Per Week

As a Regional Dedicated Class A Driver, you will be a vital part of a transportation team, responsible for safely and efficiently transporting goods to their destinations. With core skills in truck driving, and commercial driving, you will operate tractor-trailers with precision and care.

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Trucker Jobs in Winchester, KY

CDL-A Truck Driver - Start at 75 CPM K&B Transportation

Flatbed CDL Driver, Regional Route System Transport

CDL-A Truck Driver - Home Weekends TMC

Recent Flatbed CDL Driver System Transport

CDL-A Truck Driver - No-Touch Freight Ryder

Regional Truck Driver: 99% no-touch, 1099 options Dart Transit

CDL-A Truck Driver Werner Enterprises

Regional CDL A Truck Drivers Mesilla Valley Transportation (MVT)

CDL-A Truck Driver - Earn $85k-$105k/Year Barr-Nunn Transportation

CDL-A Truck Driver - Home Weekly Heartland Express

CDL A Truck Driver Mesilla Valley Transportation (MVT)

CDL-A Tanker Truck Driver Indian River Transport

CDL-A Truck Driver - 1099 - $130k+/yr Hirschbach Motor Lines

CDL-A Truck Driver Ozark Motor Lines, Inc.

CDL A OTR Truck Drivers South East Carriers, Inc.

CDL Class A Delivery Driver Performance Foodservice

Flatbed Truck Driver - $2600 Onboarding Pay Boyd Bros. Transportation Inc.

CDL A Truck Driver, $5k bonus P&S Transportation

OTR CDL-A Company Truck Driver Western Flyer Xpress

CDL-A Truck Driver - Earn $60,000-$99,000/Year Heartland Express

OTR CDL-A Truck Driver Anderson Trucking Service

CDL-A Truck Driver Riverside Transport

CDL A Truck Driver - up to $1,600+ / wk Kivi Bros Trucking

Company CDL-A Truck Driver Dollar General

CDL A Truck Driver - up to $92k / yr J&R Schugel

OTR Team CDL-A Company Truck Drivers - Multiple Locations - $15,000 Sign-On Bonus per team (limited time) Transco Lines, Inc.

CDL A Truck Driver - up to $120,000 / yr E.W. Wylie

Specialized CDL A Truck Driver - $3500 Onboarding Pay E.W. Wylie

CDL A Truck Driver Dollar General Fleet

Reefer Truck Driver - up to $130k / yr EOS Trucking

CDL A Truck Driver - 1099 - Up to $130k / yr EOS Trucking

CDL A Truck Driver - 1099 - $5,500 / wk Suit Transportation

CDL A Truck Driver - Earn $100,000-$110,000 Annually Hogan Transportation

CDL A Truck Driver (1099) - $5,500 Onboarding Pay Riverside Transport

Company CDL A Truck Driver - 100% No-Touch Riverside Transport

Local CDL A Truck Driver HandledNow

CDL A OTR Truck Drivers BBI Transportation

CDL-A - Regional Van Truckload truck driver Schneider

New Commercial Truck Driver Regional 10-4 Logistics USA

CDL-A - Dedicated nighttime truck driver Schneider

CDL A School Graduate - Regional Truck Driver 10-4 Logistics USA

CDL A - REGIONAL TRUCK DRIVERS JDEE Transport Services

Regional CDL-A Truck Driver (Southeast) Cooperidge Consulting Firm

CDL-A Flatbed Truck Driver - $0.40 to $0.48 per mile in Lexington, KY Western Express

CDL-A Flatbed Truck Driver - $0.40 to $0.48 per mile in Winchester, KY Western Express

CDL-A Flatbed Truck Driver - $0.40 to $0.48 per mile in Georgetown, KY Western Express

CDL-A Flatbed Truck Driver - $0.40 to $0.63 per mile in Lexington, KY Western Express

CDL-A Flatbed Truck Driver - $0.40 to $0.63 per mile in Winchester, KY Western Express

CDL-A Flatbed Truck Driver - $0.40 to $0.63 per mile in Georgetown, KY Western Express

Regional Dedicated CDL A driver (CREDTSC-3) SoarElite

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