Driving Jobs in Pittsfield, MA — Apply Today

As of October 2026, there are 50+ open driving jobs in Pittsfield, MA. Current pay ranges from $21 to $132,000 per year. Top hiring areas include Delivery Driver, Owner Operator and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Pittsfield, MA

$2,640 - $4,840

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Pittsfield, MA

$2,400 - $4,200

Local Merchant Delivery Network

[Part-Time] Early Morning Bakery/floral-Pittsfield

Pittsfield, MA

$2,400 - $4,200

On-Demand Tasks Network

Student Friendly:Driver Opportunity(Pittsfield)

Pittsfield, MA

$2,000 - $4,000

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Pittsfield, MA

$5,250 - $8,925

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Pittsfield, MA

$2,800 - $5,040

Secure Document Couriers

(Pittsfield)Part-Time:Night Shift Legal/document Courier

Pittsfield, MA

$2,800 - $5,000

FedEx

Driver Opportunity(Part-Time)@ Fedex-Pittsfield

Pittsfield, MA

$3,500 - $6,500

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Pittsfield, MA

$1,760 - $3,520

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Pittsfield, MA

$3,024 - $5,184

Auto Logistics Pros

Driver Opportunity(Part-Time)@ Auto Logistics Pros-Pittsfield

Pittsfield, MA

$2,800 - $4,800

Heavy Freight Logistics

Cargo Van / Box Truck Specialist needed in Pittsfield(Apply Now)

Pittsfield, MA

$5,000 - $8,500

Driving Jobs in Pittsfield — FAQ

How many driving jobs are available in Pittsfield, MA right now?
There are currently 50+ 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 50+ open routes above and apply directly.

Last updated: October 28, 2026