Delivery Driver Jobs in Pittsfield, MA — Apply Today - Page 4
65+ open delivery driver roles in Pittsfield, MA. Weekly pay, health insurance, no experience needed for many positions. See what's available in Pittsfield now.
Regional Expedite Logistics
Independent Contractor Driver - Long Distance / Regional Courier
Pittsfield, MA
$3,500 - $6,000
Urban Pedal Logistics
Independent Contractor Driver - Urban E-Bike/Scooter Courier
Pittsfield, MA
$2,275 - $4,095
On-Demand Tasks Network
Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)
Pittsfield, MA
$1,700 - $3,400
Heavy Freight Logistics
Independent Contractor Driver - Cargo Van / Box Truck Specialist
Pittsfield, MA
$5,000 - $8,500
Secure Document Couriers
Independent Contractor Driver - Night Shift Legal/Document Courier
Pittsfield, MA
$2,548 - $4,550
Local Merchant Delivery Network
Independent Contractor Driver - Early Morning Bakery/Floral
Pittsfield, MA
$2,400 - $4,200
Corporate Catering Couriers
Independent Contractor Driver - Catering Logistics
Pittsfield, MA
$3,080 - $5,280
Final Mile Delivery Co.
Independent Contractor Driver - Final Mile Parcel
Pittsfield, MA
$2,550 - $4,675
Auto Logistics Pros
Independent Contractor Driver - Auto Parts Courier
Pittsfield, MA
$3,136 - $5,376
United Parcel Service (UPS)
UPS Package Delivery Driver
Pittsfield, MA
$4,400 - $8,250
Elite Hand Courier
White-glove Specialty Courier(Gig)-Pittsfield
Pittsfield, MA
$4,000 - $6,500
CareDrop Couriers
Pharmacy Delivery Courier(Gig)-Pittsfield
Pittsfield, MA
$3,000 - $4,500
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Last updated: September 11, 2026