Driving Jobs in Pittsfield, MA — Hiring Now - Page 18

Driving companies hiring in Pittsfield, MA — 210+ open positions across CDL trucking, delivery, courier & more. Weekly pay, benefits available. Browse openings in Pittsfield.

Local Merchant Delivery Network

Early Morning Bakery/floral(PT)-Pittsfield,MA

Pittsfield, MA

$2,688 - $4,704

Secure Document Couriers

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

Pittsfield, MA

$3,080 - $5,500

Heavy Freight Logistics

Cargo Van / Box Truck Specialist at Heavy Freight Logistics

Pittsfield, MA

$5,000 - $8,500

On-Demand Tasks Network

Supplemental Income:Independent Contractor Driver-On-demand Errands

Pittsfield, MA

$2,000 - $4,000

Urban Pedal Logistics

Immediate Hire:Independent Contractor Driver-Urban E-bike/scooter

Pittsfield, MA

$2,750 - $4,950

Regional Expedite Logistics

Pittsfield Job:Independent Contractor Driver-Long Distance /

Pittsfield, MA

$3,500 - $6,000

Last updated: September 27, 2026