Driving Jobs in Pittsfield, MA — Start This Week

As of October 2026, there are 20+ open driving jobs in Pittsfield, MA. Current pay ranges from $34 to $382,200 per year. Top hiring areas include Delivery Driver, Cdl A and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Nightline Freight

Part-Time Overnight Parcel Transfer Driver – Pittsfield,MA | Part

Pittsfield, MA

$3,780 - $5,460

Peak Season Logistics

Part-Time Seasonal Holiday Package Driver(Pittsfield) | Part Time

Pittsfield, MA

$3,220 - $4,600

Metro Parcel Delivery

Evening Part-Time Urban Step Van Courier – Pittsfield | Part Time

Pittsfield, MA

$3,990 - $5,775

Health Transit Logistics

Part-Time Medical & Pharmacy Package Courier(Pittsfield) | Part

Pittsfield, MA

$2,912 - $4,095

Weekend Transit Co.

Pittsfield Part-Time Job:Weekend Parcel Delivery Driver | Part

Pittsfield, MA

$1,680 - $2,800

Heavy Haul Last Mile

Part-Time Job in Pittsfield:Heavy/bulky Item Delivery Specialist

Pittsfield, MA

$3,800 - $5,500

Flex Delivery Network

Part-Time Independent Parcel Courier Job – Pittsfield Hiring Now

Pittsfield, MA

$2,000 - $4,000

Corporate Courier Logistics

Part-Time B2B Route Logistics Driver(Pittsfield) | Part Time Job

Pittsfield, MA

$3,679 - $5,520

E-Comm Transit Solutions

Immediate Part-Time E-commerce Delivery Specialist Job –

Pittsfield, MA

$3,200 - $4,800

Local Logistics Pros

Local Package Delivery Driver|Part-Time Job|Pittsfield | Part

Pittsfield, MA

$3,000 - $4,500

Schneider National

CDL A Truck Driver - OTR Dry Van

Pittsfield, MA

$75,000 - $96,000

Crete Carrier

CDL A Truck Driver - Regional Dry Van Home Weekly

Pittsfield, MA

$72,000 - $92,000

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: October 05, 2026