Owner Operator Jobs in Chestertown, MD (79)

CDL-A Drivers / $0.59 - $0.63 CPM / Regional & OTR Routes

Ozark Motor Lines

Aberdeen Proving Ground, MD

Driver

Dental Insurance

Vision Insurance

Licensed CDL-A Truck Driver - Home Weekends - Earn Up to $100,000/Year

TMC

Dundalk, MD

Driver

Health Insurance

Dental Insurance

Vision Insurance

Education

$100k / year

CDL-A Truck Driver - Home Daily - Average $91,000/Year - 3 Months Exp.

C.R. England

Chestertown, MD

Driver

401(k)

$91k / year

School Psychologist

Supplemental Health Care

Chestertown, MD

New

Part-Time

Hourly

401(k)

Dental Insurance

Vision Insurance

$58 - $62 / hour

Experienced CDL-A Truck Driver - Earn Up to $1,575/Week + No-Touch

J&R Schugel

Dundalk, MD

New

Driver

Dental Insurance

Vision Insurance

$1,575 / week

CDL-A Truck Driver - Recent Grads Welcome - Home Weekends

TMC

Dundalk, MD

Driver

Health Insurance

Dental Insurance

Vision Insurance

$1,350 - $1,600 / week

‌

1 Year Exp Req. - CDL-A Truck Driver - Avg $92,254/Yr + Route Options

Crete Carrier

Dundalk, MD

Driver

401(k)

Dental Insurance

Vision Insurance

$92.3k / year

‌

Owner Operators

Clark Transfer

Middletown, DE

New

Health Insurance

$3,750 - $4,250 / month

‌

OTR Owner Operator Driver Job in Bridgeton, NJ(Up to $240K+/yr)

GREATWIDE

Massey, MD

Driver

$240k / year

‌

OTR Lease Contractor Truck Driver Job in Parkville, MD ($1.62 CPM)

CRST The Transportation Solution

Chestertown, MD

Driver

$2,000 sign-on bonus

‌

CDL-A Lease Truck Driver Job in Dover, DE ($1.62 CPM)

CRST The Transportation Solution

Chestertown, MD

Driver

$2,000 sign-on bonus

‌

CDL-A Lease Purchase Reefer Truck Driver Job in Chester, PA($9K Minimum + 2026 Truck in 6wk)

Hurricane Express

Middletown, DE

New

Driver

$9,000 / month

‌

CDL-A Dry Van Truck Driver Job in Dover, DE ( $.57-$.64 CPM )

US Xpress

Chestertown, MD

Driver

$1,000 sign-on bonus

401(k)

Dental Insurance

Vision Insurance

Education

‌

CDL-A Dry Van Truck Driver Job in Easton, MD( $.57-$.64 CPM )

US Xpress

Chestertown, MD

Driver

$1,000 sign-on bonus

401(k)

Dental Insurance

Vision Insurance

Education

‌

CDL-A Dry Van Truck Driver Job in Bel Air, MD( $.57-$.64 CPM )

US Xpress

Chestertown, MD

New

Driver

$1,000 sign-on bonus

401(k)

Dental Insurance

Vision Insurance

Education

‌

CDL-A OTR/Regional Truck Driver

DB Schenker

Dundalk, MD

New

Driver

$700 / week

‌

CDL-A Local Yard Truck Driver Job in Oxford, PA ($21/hr)

First Fleet

Worton, MD

Hourly

Driver

PTO

Dental Insurance

Vision Insurance

$21 / hour

‌

Class A Reefer Truck Driver Job in Wilmington, DE($1,900-$2,100/WK)

Holland Enterprises

Georgetown, MD

Driver

401(k)

Dental Insurance

Vision Insurance

$1,900 - $2,100 / week

‌

CDL-A Dry Van Truck Driver Job in New Castle, DE ( $.57-$.64 CPM )

US Xpress

Georgetown, MD

New

Driver

$1,000 sign-on bonus

401(k)

Dental Insurance

Vision Insurance

Education

‌

CDL Class A Truck Driver Job in Columbia, MD(Up to $90k/yr)

Western Express

Rock Hall, MD

Driver

401(k)

Dental Insurance

Vision Insurance

$90k / year

‌

CDL-A Dry Van Driving Job in Middletown, DE($.52-$.57 CPM)

Summitt Trucking

Chestertown, MD

Driver

401(k)

Health Insurance

Dental Insurance

Vision Insurance

‌

Class A Dry Van Driving Job in Smyrna, DE($.52-$.57 CPM)

Summitt Trucking

Chestertown, MD

New

401(k)

Health Insurance

Dental Insurance

Vision Insurance

‌

OTR Class A Reefer Driver Job in Baltimore, MD($1,900-$2,100/WK)

Holland Enterprises

Chestertown, MD

Driver

401(k)

Dental Insurance

Vision Insurance

$1,900 - $2,100 / week

‌

CDL-A Reefer Truck Driving Job in Annapolis, MD($.62-.$70CPM)

K&B Transportation

Chestertown, MD

Driver

Dental Insurance

Vision Insurance

$70 / hour

‌

CDL-A Dry Van Truck Driver Job in Parkton, MD( $.57-$.64 CPM )

US Xpress

Aberdeen Proving Ground, MD

Driver

$1,000 sign-on bonus

401(k)

Dental Insurance

Vision Insurance

Education

‌

CDL-A Dry Van Driving Job in Bear, DE ( $.57-$.64 CPM )

US Xpress

Chestertown, MD

Driver

$1,000 sign-on bonus

401(k)

Dental Insurance

Vision Insurance

Education

‌

Class A CDL Dry Van Driving Job in Baltimore, MD ( $.57-$.64 CPM )

US Xpress

Chestertown, MD

New

Driver

$1,000 sign-on bonus

401(k)

Dental Insurance

Vision Insurance

Education

‌

Franchise Business Consultant

International Dairy Queen

🌎 Remote

New

Remote

401(k)

Dental Insurance

Parental Leave

$92.8k - $113.7k / year

‌

Geriatric Nursing Assistant (GNA)

ACTS Retirement-Life Communities

Chestertown, MD

Dental Insurance

Vision Insurance

Education

$17.82 - $26.38 / hour

‌

Home Services Geriatric Nursing Assistant (GNA)

ACTS Retirement-Life Communities

Chestertown, MD

Dental Insurance

Vision Insurance

Education

$16.79 - $24.52 / hour

‌

Certified Nursing Assistant (CNA)

ACTS Retirement-Life Communities

Chestertown, MD

New

Dental Insurance

Vision Insurance

Education

$17.30 - $25.76 / hour

‌

Independent Travel Consultant: Contractor - Build Your Own Travel AgencyBusiness

Shaw Dream Destinations / Whimsical Wanders Travel

🌎 Remote

Remote

‌

Independent Contractor / Forensic Psychologist / Workers Compensation

Genesis Psychology Group

🌎 Remote

Part-Time

Remote

Flexible Schedule

Job Description

Working as an Owner Operator in Chestertown, MD

There are 79 Owner Operator opportunities available in Chestertown, MD all with unique requirements.

The Owner Operator job description includes those who own and operate their own trucks who are responsible for safely hauling cargo. Owner Operators earn a good income and are their own boss, as well as hiring their team. They may provide services covering short or long distances and deliver any type of resource from goods to people.

Owner Operator jobs near Chestertown, MD

Owner Operators in Chestertown, MD Resume Data

Average Experience for Owner Operators in Chestertown, MD

More than 10 years: 79%
6-10 years: 14%
3-5 years: 5%
1-2 years: 1%
Less than 1 year: 1%

Educational Background for Owner Operators in Chestertown, MD

Diploma: 61%
Associates: 16%
Bachelors: 15%
Masters: 7%
Doctorate: 2%

Top Skill for Owner Operators in Chestertown, MD

Work style: Reliability: 18%
Customer focus & orientation: 17%
Attention to detail: 14%
Customer service: 10%
Delivery driver: 9%
Sales skills: 9%
Management & leadership skills: Planning & execution: 6%
Work motivation: 6%
Administrative assistant/receptionist: 5%
Mechanical knowledge: 5%

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