High-paying driving jobs in Pittsfield
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 161 high-paying for you in Pittsfield, MA. These driving jobs pay well, with salaries between $55,288 to $348,878 per hour. Popular roles include Truck Driver, Delivery Driver and Driver.
Job title
Updated Oct 20, 2026
Job title
Pittsfield, MA
Massachusetts
Job openings (Pittsfield)
Owner Operator Driver
Pittsfield
$6,383
per week
Massachusetts
$5,545
per week
Truck Driver
Pittsfield
$2,477
per week
Massachusetts
$1,554
per week
Driver (independent Contractor)
Pittsfield
$27.85
per hour
Massachusetts
$31.35
per hour
Delivery Driver
Pittsfield
$20.38
per hour
Massachusetts
$21.03
per hour
Van Driver
Pittsfield
$20.26
per hour
Massachusetts
$21.20
per hour
Driver
Pittsfield
$18.94
per hour
Massachusetts
$22.08
per hour
Job descriptions below are for educational purposes. Please refer to the employer's job description for complete details.
-
Owner Operator Driver
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Please refer to the employers job description for complete details.
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.
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 4 jobsAverage pay
Pittsfield
$6,383 per weekMassachusetts
$5,545 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.
Truck Driver jobs take 93 days on average from job posting to starting date. Currently, 2% of job openings are part-time roles.
See 52 jobsAverage pay
Pittsfield
$2,477 per weekMassachusetts
$1,554 per weekSkills
- Driving
- Load & unload
- Bus driving
- Commercial driving
-
Driver (independent Contractor)
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Please refer to the employers job description for complete details.
Independent contractor drivers use their own vehicles for deliveries, managing their own schedules and client interactions. Strong self-management skills, reliable transportation and knowledge of local routes are essential in this role.
Driver (independent Contractor) jobs take 59 days on average from job posting to starting date. Currently, 92% of job openings are part-time roles.
See 18 jobsAverage pay
Pittsfield
$27.85 per hourMassachusetts
$31.35 per hour -
Delivery Driver
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Please refer to the employers job description for complete details.
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.
Delivery Driver jobs take 170 days on average from job posting to starting date. Currently, 33% of job openings are part-time roles.
See 52 jobsAverage pay
Pittsfield
$20.38 per hourMassachusetts
$21.03 per hourSkills
- Driving
- Load & unload
- Bus driving
- Hindi
- English
-
Van Driver
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Please refer to the employers job description for complete details.
Van Drivers transport goods or passengers safely, maintain vehicle compliance, and ensure timely delivery. Valid driver's license, safe driving record, and reliability are essential.
Van Driver jobs take 67 days on average from job posting to starting date. Currently, 23% of job openings are part-time roles.
See 7 jobsAverage pay
Pittsfield
$20.26 per hourMassachusetts
$21.20 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.
Driver jobs take 81 days on average from job posting to starting date. Currently, 46% of job openings are part-time roles.
See 28 jobsAverage pay
Pittsfield
$18.94 per hourMassachusetts
$22.08 per hourSkills
- Driving
- Load & unload
- Bus driving
- Automotive repair