Driving Jobs in Pittsfield, MA — Apply Today - Page 14

Driving companies hiring in Pittsfield, MA — 160+ open positions across CDL trucking, delivery, courier & more. Weekly pay, benefits available. Browse openings in Pittsfield.

DoorDash

Apply Now:Catering Delivery Driver in Pittsfield | Hiring

Pittsfield, MA

$4,200 - $6,800

Grubhub

Recruiting in Pittsfield:Part-time Delivery Driver | Hiring

Pittsfield, MA

$600 - $1,800

Uber Eats

E-bike Delivery Driver Needed-Pittsfield Area | Hiring

Pittsfield, MA

$2,400 - $4,200

Amazon Flex

Pittsfield Contractor Package Delivery Driver | Hiring

Pittsfield, MA

$3,600 - $5,800

Last updated: September 20, 2026