Driving Jobs in Pittsfield, MA — See Openings - Page 8

160+ driving jobs in Pittsfield, MA hiring now — CDL, delivery driver, courier & more. $18–$90K+, many with benefits. See what's open in Pittsfield.

CRST The Transportation Solution

CDL A Truck Driver - OTR Team Driver

Pittsfield, MA

$76,120 - $96,800

The Home Depot

Driver Opportunity(Part-Time)@ The Home Depot-Pittsfield

Pittsfield, MA

$23 - $31

Sherwin-Williams

Part-Time Paint Store Delivery Driver-Commercial

Pittsfield, MA

$18 - $24

AAA Roadside

(Pittsfield)Part-Time:Driver Opportunity

Pittsfield, MA

$28 - $40

DoorDash

Pittsfield:Delivery Driver-Food Delivery Part Time Evenings

Pittsfield, MA

$15 - $22

Regional Expedite Logistics

Regional Expedite Logistics is hiring a Independent Contractor

Pittsfield, MA

$3,500 - $6,000

GoPuff

Pittsfield Contractor Convenience Store Delivery Driver | Hiring

Pittsfield, MA

$2,800 - $4,500

DoorDash

Morning Shift Delivery Driver•Pittsfield,MA•Doordash | Hiring

Pittsfield, MA

$2,700 - $4,600

DoorDash

Pittsfield Job:Delivery Driver(Contractor) | Hiring

Pittsfield, MA

$3,000 - $5,200

Amazon Flex

Flexible Gig:Delivery Driver-Independent Contractor(Pittsfield)

Pittsfield, MA

$18 - $25

First Student

Pittsfield School Bus Driver-CDL B With Passenger And S Endorsements

Pittsfield, MA

$21 - $30

Medline Industries

Medline Medical Supply Delivery Driver

Pittsfield, MA

$19 - $24

Last updated: May 13, 2026