Driving Jobs in Pittsfield, MA — Now Hiring - Page 3

Driving jobs near Pittsfield — 200+ positions open now. CDL & non-CDL roles, no experience required for many positions. Benefits, weekly pay & sign-on bonuses.

Grubhub

Part-Time Night Shift Courier – Pittsfield,MA | Part Time Job

Pittsfield, MA

$2,800 - $4,800

Uber

Pittsfield Career:Campus Area Ubereats Driver at Uber | Hiring

Pittsfield, MA

$2,600 - $4,800

Regional Expedite Logistics

Pittsfield Contractor Opening:Independent Contractor Driver-Long

Pittsfield, MA

$3,500 - $6,000

Grubhub

Part-Time Large Order Delivery Driver(Pittsfield,MA)|Grubhub

Pittsfield, MA

$3,500 - $6,000

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Pittsfield, MA

$2,380 - $4,250

Flex Delivery Network

Part-Time Independent Parcel Courier Job in Pittsfield | Part

Pittsfield, MA

$2,000 - $4,000

Heavy Haul Last Mile

Part-Time Heavy/bulky Item Delivery Specialist – Pittsfield

Pittsfield, MA

$3,496 - $5,060

Sysco Corporation

Pittsfield Flexible Role:Sysco Local CDL-A Delivery Truck Driver

Pittsfield, MA

$6,000 - $9,000

Prime Beverage Distributors

Pittsfield Part-Time:Beverage Distribution Route Driver

Pittsfield, MA

$5,000 - $8,000

Uber

Immediate Opening in Pittsfield for a Black Driver | Hiring

Pittsfield, MA

$4,950 - $8,250

Lyft

Pittsfield:Premium Rideshare Driver(Contractor,$4.5k-$7.5k/Month)

Pittsfield, MA

$4,500 - $7,500

Instacart

Instacart Full-Service Shopper

Pittsfield, MA

$2,625 - $4,725

Last updated: May 03, 2026