Driving Jobs in Pittsfield, MA — See Openings - Page 21
250+ driving jobs in Pittsfield, MA hiring now — CDL, delivery driver, courier & more. $18–$90K+, many with benefits. See what's open in Pittsfield.
Last Mile Logistics Network
Independent Contractor Driver - Last-Mile Logistics
Pittsfield, MA
$2,464 - $4,400
Auto Logistics Pros
Independent Contractor Driver - Auto Parts Courier
Pittsfield, MA
$2,464 - $4,224
Final Mile Delivery Co.
Independent Contractor Driver - Final Mile Parcel
Pittsfield, MA
$3,000 - $5,500
Corporate Catering Couriers
Independent Contractor Driver - Catering Logistics
Pittsfield, MA
$3,185 - $5,460
Local Merchant Delivery Network
Independent Contractor Driver - Early Morning Bakery/Floral
Pittsfield, MA
$2,592 - $4,536
Secure Document Couriers
Independent Contractor Driver - Night Shift Legal/Document Courier
Pittsfield, MA
$3,219 - $5,750
Heavy Freight Logistics
Independent Contractor Driver - Cargo Van / Box Truck Specialist
Pittsfield, MA
$5,250 - $8,925
On-Demand Tasks Network
Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)
Pittsfield, MA
$1,700 - $3,400
Urban Pedal Logistics
Independent Contractor Driver - Urban E-Bike/Scooter Courier
Pittsfield, MA
$2,625 - $4,725
Regional Expedite Logistics
Independent Contractor Driver - Long Distance / Regional Courier
Pittsfield, MA
$3,185 - $5,460
Last updated: October 03, 2026