CDL Truck Driver Jobs in Chestertown, MD

A CDL (Commercial Driver's License) Truck Driver plays a critical role in the transportation industry by ensuring the safe and timely delivery of goods. Their tasks include planning routes, inspecting vehicles for mechanical items and safety issues, and complying with truck driving rules and regulations (size, weight, route designations, parking, and break periods). It is their responsibility to manage loads, keep logs of their activities, report any incidents or issues encountered, and maintain a professional and customer-focused attitude. CDL Truck Drivers are key links in the supply chain, as they facilitate the movement of goods from manufacturers to consumers, impacting sectors such as retail, food services, and manufacturing.

Prior to becoming a CDL Truck Driver, an individual might have held roles such as a delivery driver, warehouse worker, or freight handler. These positions provide the necessary experience in handling goods, understanding delivery protocols, and operating within the logistics sector. In addition to prior experience, a CDL Truck Driver must possess a Commercial Driver's License (CDL) and often undergo further specialized training depending on the type of materials they transport. Essential skills for this role include a solid understanding of road safety, excellent time management to ensure timely deliveries, mechanical knowledge to perform basic vehicle maintenance, and physical stamina to manage long hours on the road.

1-15 of 23 Jobs

Top 50% of OTR CDL A drivers avg. $92,254/Year

Kenton, DE (22 miles from Chestertown, MD)
7 hours ago

Kenton, DE (22 miles from Chestertown, MD)
7 hours ago

Drivers from the First State will find first rate opportunities with Crete Carrier and Shaffer Trucking, whether youre looking for frequent home time or prefer regional or national OTR. Salary:...

OTR CDL A Drivers Needed-Top 50% average $92,254-21 Days Out

Kenton, DE (22 miles from Chestertown, MD)
7 hours ago

Kenton, DE (22 miles from Chestertown, MD)
7 hours ago

Shaffer Trucking offers a 21-Day Out Moving National Freight. Salary: Top 50% average $92,254 per year CPM: Starting pay $.63 to $.66 cpm Experience: One-year verifiable tractor trailer experience...

Truck Driver - Hiker/Vehicle Transporter/CDL - Part Time - 1st Shift

Belcamp, MD (21 miles from Chestertown, MD)
8 hours ago

Belcamp, MD (21 miles from Chestertown, MD)
8 hours ago

Penske Truck Leasing seeks highly motivated and qualified applicants to fill the unique position of Hiker (Vehicle Transporter/Truck Driver). This position is responsible for vehicle delivery and...

Local CDL-A Truck Driver - Home Daily - Earn $30.24/Hour

Essex, MD (20 miles from Chestertown, MD)
9 hours ago

Essex, MD (20 miles from Chestertown, MD)
9 hours ago

Have a Class-A CDL with doubles/triples, tanker, and hazardous materials endorsements and no automatic restriction....

Class A Truck Driver

White Marsh, MD (22 miles from Chestertown, MD)
2 days ago

White Marsh, MD (22 miles from Chestertown, MD)
2 days ago

Class A Truck Driver White Marsh, Maryland - Posted on July 9, 2025 Published By Lindsay Strohman Now hiring CDL Class A Truck Drivers in Dundalk! Trillium Drivers is now seeking CDL Class A...

Local Cdl A Truck Driver / Yard Jockey

Aberdeen, MD (22 miles from Chestertown, MD)
2 days ago

Aberdeen, MD (22 miles from Chestertown, MD)
2 days ago

Qualifications Valid Commercial Driver's License Class A Proven experience as a class A CDL driver with a satisfactory MVR driving record....

Home depot delivery driver box truck

Sparrows Point, MD (18 miles from Chestertown, MD)
3 days ago

Sparrows Point, MD (18 miles from Chestertown, MD)
3 days ago

Looking for a team of two job consist of going to our Home Depot customer house after our flatbed driver drop off the merchandise and we bring it in inside and pack product at house so it can be...

Local Delivery Driver - CDL A

White Marsh, MD (22 miles from Chestertown, MD)
3 days ago

White Marsh, MD (22 miles from Chestertown, MD)
3 days ago

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, protected veteran status, or...

Dedicated Class A Tanker Driver

Essex, MD (20 miles from Chestertown, MD)
3 days ago

Essex, MD (20 miles from Chestertown, MD)
3 days ago

Centerline is hiring local Class A tanker drivers that will be dedicated to the team. We are looking for local truck drivers who have expertise in navigating the area What you'll do: Haul...

$90,000 - $100,000/ Annual Dedicated Class A Tanker Driver

Essex, MD (20 miles from Chestertown, MD)
5 days ago

Essex, MD (20 miles from Chestertown, MD)
5 days ago

opportunities, trucking company, student truck drivers, Class A truck driver, class A cdl, semi driver, company truck driver, transport, trucking jobs, cdl truck driver training, truck driver schools...

Driver - CDL A

Joppa, MD (22 miles from Chestertown, MD)
6 days ago

Joppa, MD (22 miles from Chestertown, MD)
6 days ago

Join Our Team! Sunbelt Rentals strives to be the customer's first choice in the equipment rental industry. From pumps to scaffolding to general construction tools, we aim to be the only call...

Local Delivery Driver - CDL A

White Marsh, MD (22 miles from Chestertown, MD)
6 days ago

White Marsh, MD (22 miles from Chestertown, MD)
6 days ago

view our Driver Job Preview Video *Greatly preferred that candidates have no restrictions on the license and also be able to drive a 10-speed manual transmission. Position will deliver to all...

CDL A Driver - Local Home Daily

Barclay, MD (12 miles from Chestertown, MD)
6 days ago

Barclay, MD (12 miles from Chestertown, MD)
6 days ago

Reeb Millwork an SBP Brand is currently looking for a CDL Class A Driver to join our VALUES based organization. Perks of working at Reeb Millwork: Home daily - working Monday-Friday $26/Hr....

CDL-A Truck Driver - Home Time Options - Start at 59-63 CPM + No-Touch

Dundalk, MD (22 miles from Chestertown, MD)
8 days ago

Dundalk, MD (22 miles from Chestertown, MD)
8 days ago

Ozark Motor Lines is now hiring CDL-A OTR Company Drivers Multiple OTR Home Time Options Available $0.59 - $0.63 Starting Pay per Mile* - No-Touch Freight Pay & Details: $0.59 - $0.63 Starting pay...

CDL-A - Intermodal truck driver

Edgewood, MD (20 miles from Chestertown, MD)
14 days ago

Edgewood, MD (20 miles from Chestertown, MD)
14 days ago

Qualifications + Valid Class A Commercial Driver's License (CDL). + Drivers on this account are required to drive at night. + Tanker endorsement and HazMat endorsement are strongly preferred. + Live...

View all 23 jobs

Demographic Data for Chestertown, MD

Moving to Chestertown, MD? Find some basic demographic data about Chestertown, MD below.

Median Age

Average Household Income

Home Value vs Household Income in Chestertown, MD

Local

National

Total Population

12,726

Number of Businesses

422

City Size

Medium/Sm

CDL Truck Driver Online Courses and Training Opportunities

iHireTransportation curates thousands of courses in order to recommend the best ones to help further your career. If you register for a course using the links on our site, we may receive a small commission.

How to Get Your Class A CDL and Become a Truck Driver

Trucking can offer you many opportunities to earn a great living and have some adventure in the process. It can also even lead to you owing your own successful trucking business - if that is...

How To Become a Truck Driver

Let's talk about the money, most truck drivers can expect to earn $30,000-$40,000 in their 1st year. I know some drivers who work as Solo drivers and decide to give up their apartments so they can...

Truck Driver Recruiter Certification Course

Introducing the Ultimate Online Course for Aspiring Truck Driver Recruiters!Are you ready to embark on a lucrative work-from-home career? Look no further! Our comprehensive online course is...

Salary for CDL Truck Driver Jobs in Chestertown, MD

Estimated salary range based on data from US Bureau of Labor Statistics (BLS) and iHireTransportation research efforts.

Licensing / Certification

Required or preferred licenses and certifications for CDL Truck Driver positions.

Highest Education Level

CDL Truck Drivers in Chestertown, MD offer the following education background

High School or GED

37.4%

Vocational Degree or Certification

23.0%

Bachelor's Degree

16.0%

Associate's Degree

13.3%

Master's Degree

4.5%

Some College

3.7%

Some High School

1.4%

Doctorate Degree

0.6%

Average Work Experience

Here's a breakdown of the number of years' experience offered by CDL Truck Drivers in Chestertown, MD

None

39.3%

1-2 years

31.7%

Less than 1 year

29.0%

Qualifications / Skill Sets

The following top skills are often required or desired to land a CDL Truck Driver position

In-Demand skills () are the most popular among employers according to the current jobs in our database. Last updated today!

Other Career Titles

Here are some other career titles that require similar skills

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