Driving Jobs in Pittsfield, MA — Open Positions

As of September 2026, there are 20+ open driving jobs in Pittsfield, MA. Current pay ranges from $14 to $90,000 per year. Top hiring areas include Delivery Driver and Box Truck. New roles are posted daily — listings on this page are verified and updated regularly.

Transportation Concepts

Part-Time Job in Pittsfield – Non-cdl Box Truck Delivery Driver

Pittsfield, MA

$20 - $26

Performance Foodservice

Part-Time CDL Class A Route Delivery Driver|Pittsfield,MA | Part

Pittsfield, MA

$70,000 - $90,000

Spark Driver

Part-Time Walmart Spark Delivery Driver(Pittsfield,MA)|Spark

Pittsfield, MA

$15 - $21

Domino's Pizza

Pittsfield Part-Time:Delivery Driver(Now Hiring) | Part Time Job

Pittsfield, MA

$14 - $22

Quest Diagnostics

Part-Time Medical Courier Delivery Driver Job in Pittsfield

Pittsfield, MA

$15 - $22

UPS

Part-Time Package Delivery Driver – Pittsfield,MA | Part Time Job

Pittsfield, MA

$23 - $30

DoorDash

Pittsfield Part-Time:Delivery Driver-Dasher(Hiring) | Part Time

Pittsfield, MA

$15 - $25

Amazon Flex

Pittsfield Part-Time Job:Delivery Driver-Independent Contractor

Pittsfield, MA

$18 - $25

FedEx

Pittsfield Part-Time Job:Ground Delivery Driver | Part Time Job

Pittsfield, MA

$21 - $26

Amazon DSP

Weekend Part-Time Delivery Driver – Pittsfield | Part Time Job

Pittsfield, MA

$22 - $28

Domino's Pizza

Pizza Delivery Driver

Pittsfield, MA

$2,500 - $4,200

Amazon DSP

Amazon DSP Delivery Driver

Pittsfield, MA

$3,920 - $5,376

Driving Jobs in Pittsfield — FAQ

How many driving jobs are available in Pittsfield, MA right now?
There are currently 20+ open driving jobs in Pittsfield, MA. They range from CDL-A truck driving and local home-daily routes to delivery, box truck, bus and non-CDL driving work. New routes are added daily.
How much do driving jobs pay in Pittsfield?
Pay in Pittsfield depends on the licence and the type of driving: delivery and non-CDL routes usually run $18–$26/hr, local CDL work $22–$32/hr, and CDL-A regional or OTR seats $1,200–$1,900 a week. Night runs and specialised freight such as flatbed or tanker pay more.
Are there driving jobs in Pittsfield with no experience?
Yes. Many employers in Pittsfield run paid CDL training or hire recent CDL school graduates, and non-CDL delivery, shuttle and rideshare work needs only a regular licence and a clean record.
Can I get a driving job in Pittsfield that is home every night?
Local routes in Pittsfield are home daily, including delivery, box truck, yard, dump truck and local CDL-A work. Regional runs get you home weekly, and OTR means longer stretches away for higher weekly pay.
Do I need a CDL to drive in Pittsfield?
Not for every job. Cargo van, sprinter, courier, shuttle and most 26' box truck routes need only a regular driver's licence. A CDL-B is needed for heavier straight trucks and buses, and a CDL-A for tractor-trailers.
What do employers check before hiring a driver in Pittsfield?
Your driving record for the last 3–5 years, a background check, and for commercial roles a DOT physical and drug test. Most insurers require drivers to be at least 21 for interstate work.
Which companies are hiring drivers immediately in Pittsfield?
Many carriers, delivery firms and local fleets in Pittsfield hire on a rolling basis, with start dates often within one to two weeks of applying. Browse the 20+ open routes above and apply directly.

Last updated: September 28, 2026