High-paying driving jobs in Annapolis
Driving involves operating vehicles to transport passengers or goods safely. Drivers must follow traffic laws and ensure the vehicle's maintenance. They need good reflexes, focus, and the ability to navigate roads efficiently, often in various weather conditions.
We found 1,331 high-paying for you in Annapolis, MD. These driving jobs pay well, with salaries between $41,704 to $194,045 per hour. Popular roles include Truck Driver, Owner Operator Driver and Delivery Driver.
Job title
Updated Oct 25, 2026Owner Operator Driver
Annapolis
Maryland
Truck Driver
Annapolis
Maryland
Bus Driver
Annapolis
Maryland
Drivers Helper
Annapolis
Maryland
Delivery Driver
Annapolis
Maryland
Parts Driver
Annapolis
Maryland
Driver
Annapolis
Maryland
Job descriptions below are for educational purposes. Please refer to the employer's job description for complete details.
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Owner Operator Driver
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Owner Operator Drivers transport goods safely, manage logistics, and ensure compliance with regulations. Skills in route planning, knowledge of trucking regulations, and strong self-discipline are essential.
The top companies hiring Owner Operator Driver in Annapolis, MD are Evans Network of Companies (10 jobs), Forward Air (2 jobs), and Page Transportation & Page E.T.C. (1 job).
Owner Operator Driver jobs take 68 days on average from job posting to starting date. Currently, 2% of job openings are part-time roles.
See jobsAverage pay
Annapolis
$3,550 per weekMaryland
$3,056 per week -
Truck Driver
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Please refer to the employers job description for complete details.
Truck Drivers transport goods, maintain logs, and ensure vehicle safety. A valid commercial driver's license, adherence to regulations, and time management skills are essential. Experience in long-haul driving is advantageous.
The top companies hiring Truck Driver in Annapolis, MD are Crosby trucking Service, Inc. (3 jobs), Alabama Motor Express (2 jobs), and Cassens Transport (2 jobs).
Truck Driver jobs take 93 days on average from job posting to starting date. Currently, 2% of job openings are part-time roles.
See jobsAverage pay
Annapolis
$1,698 per weekMaryland
$1,728 per weekSkills
- Driving
- Load & unload
- Bus driving
- Commercial driving
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Bus Driver
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Bus Drivers transport passengers, ensure on-time service, and maintain vehicle safety. Essential qualifications include driving license, route navigation proficiency, and passenger communication skills.
The top companies hiring Bus Driver in Annapolis, MD are CITY OF ANNAPOLIS (1 job), Chesapeake Charter, Inc. (1 job), and Saint Marys Catholic Church (1 job).
Bus Driver jobs take 105 days on average from job posting to starting date. Currently, 49% of job openings are part-time roles.
See jobsAverage pay
Annapolis
$28.29 per hourMaryland
$24.58 per hourSkills
- Driving
- Forklift
- Freight
- Load & unload
- Automotive repair
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Drivers Helper
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Driver helpers assist with loading, unloading and navigating delivery routes, ensuring timely service. Strong teamwork, physical stamina and communication skills are essential in this role.
Drivers Helper jobs take 92 days on average from job posting to starting date. Currently, 84% of job openings are part-time roles.
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Annapolis
$20.85 per hourMaryland
$18.76 per hourSkills
- Load & unload
- Driving
- Bus driving
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Delivery Driver
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Delivery Drivers transport goods safely, navigate routes efficiently, and manage timely deliveries. They need valid driving licenses, strong knowledge of navigation tools, and effective time management to meet schedule demands and ensure customer satisfaction.
The top companies hiring Delivery Driver in Annapolis, MD are Papa John's (1 job), Domino's (1 job), and Fisher Auto Parts, Inc (1 job).
Delivery Driver jobs take 170 days on average from job posting to starting date. Currently, 37% of job openings are part-time roles.
See jobsAverage pay
Annapolis
$18.71 per hourMaryland
$20.29 per hourSkills
- Driving
- Load & unload
- Bus driving
- Hindi
- English
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Parts Driver
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Parts drivers deliver automotive parts to dealerships and repair shops, ensuring timely arrivals. Attention to detail, knowledge of parts and strong driving skills are essential in this role.
Parts Driver jobs take 76 days on average from job posting to starting date. Currently, 17% of job openings are part-time roles.
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Annapolis
$18.25 per hourMaryland
$18.30 per hour -
Driver
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Please refer to the employers job description for complete details.
Drivers operate vehicles safely, follow schedules, and handle delivery documentation. A valid driver's license, time management skills, and navigation abilities are essential.
The top companies hiring Driver in Annapolis, MD are My City Transportation (2 jobs), Asbury Automotive Group (1 job), and Chick-fil-A Restaurants (1 job).
Driver jobs take 81 days on average from job posting to starting date. Currently, 42% of job openings are part-time roles.
See jobsAverage pay
Annapolis
$18.01 per hourMaryland
$21.16 per hourSkills
- Driving
- Load & unload
- Bus driving
- Automotive repair