Delivery Driver Jobs in Pittsfield, MA — Immediate Openings

As of May 2026, there are 169 delivery driver openings in Pittsfield, MA. Local pay ranges from $440 to $9,350/year. Listings are updated daily — benefits start Day 1 for most positions.

Morning Express Couriers

Driver Opportunity needed in Pittsfield(Apply Now)

Pittsfield, MA

$2,200 - $3,800

Lyft

Pittsfield XL Rideshare Driver(Contractor)-Lyft | Hiring

Pittsfield, MA

$4,000 - $6,500

Grubhub

Pittsfield Part-Time:Early Morning Driver(Apply Today) | Part

Pittsfield, MA

$2,200 - $3,800

Local Logistics Network

Independent Contractor Driver-Medical Courier Needed-Pittsfield Area

Pittsfield, MA

$3,449 - $5,750

Uber

Night Shift Rideshare Driver Needed-Pittsfield Area | Hiring

Pittsfield, MA

$3,200 - $5,500

Grubhub

Grubhub Delivery Driver

Pittsfield, MA

$2,200 - $3,960

Peak Season Logistics

Flexible Part-Time Seasonal Holiday Package Driver in Pittsfield

Pittsfield, MA

$3,500 - $5,000

ProWear Logistics

Part-Time Uniform & Apparel Route Driver in Pittsfield

Pittsfield, MA

$3,500 - $5,500

Lyft

Apply Now:Event Rideshare Driver in Pittsfield | Hiring

Pittsfield, MA

$2,800 - $5,000

Shipt

Weekend Shift:Courier-Pittsfield

Pittsfield, MA

$2,000 - $3,500

Secure Legal Logistics

Legal & Secure Document Courier

Pittsfield, MA

$3,500 - $5,500

Shipt

Start ASAP:Evening & Night Shift Courier(Pittsfield)

Pittsfield, MA

$2,800 - $4,800

Delivery Driver Jobs in Pittsfield — FAQ

How many delivery driver jobs are open in Pittsfield, MA?
There are currently 169+ delivery driver positions in Pittsfield, MA. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Pittsfield?
Delivery Driver pay in Pittsfield varies by employer, route type, and experience level. Many positions offer shift differentials, mileage bonuses, and sign-on bonuses. Browse the listings above to see pay details for each opening.
Do delivery driver jobs in Pittsfield require experience?
Many delivery driver positions in Pittsfield welcome entry-level applicants. Employers like Amazon, FedEx, and UPS often provide paid training. CDL positions may require a valid commercial license — check individual listings for specific requirements.
How do I apply for delivery driver jobs in Pittsfield?
Browse the 169+ delivery driver listings above, click on any position for full details including pay, schedule, and requirements, then follow the application link. Most driving positions have a simple online application.

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Other Driving Jobs in Pittsfield

Other Driving Jobs in Pittsfield

14 open positions

Part-Time Driving Jobs in Pittsfield

6 open positions

Cdl Driver Jobs in Pittsfield

3 open positions

Weekend Driving Jobs in Pittsfield

3 open positions

Grocery Jobs in Pittsfield

2 open positions

DSP Driver Jobs in Pittsfield

2 open positions

Warehouse Jobs in Pittsfield

1 open positions

Last updated: May 03, 2026