Delivery Driver Jobs in Pittsfield, MA — Hiring Now

As of April 2026, there are 121 delivery driver openings in Pittsfield, MA. Local pay ranges from $425 to $8,500/year. Listings are updated daily — benefits start Day 1 for most positions.

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Pittsfield, MA

$2,940 - $5,040

Uber

Flexible Gig:Night Shift Ubereats Courier(Pittsfield) | Hiring

Pittsfield, MA

$2,800 - $4,800

Wholesale Transit Partners

Start ASAP:Driver Opportunity(Pittsfield)

Pittsfield, MA

$3,040 - $5,225

DoorDash

DoorDash Delivery Driver (Dasher)

Pittsfield, MA

$2,200 - $3,960

Auto Logistics Pros

Auto Logistics Pros Needs Independent Contractor Driver-Auto Parts

Pittsfield, MA

$2,800 - $4,800

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Pittsfield, MA

$3,500 - $6,000

Auto Logistics Pros

Independent Contractor Driver-Auto Parts

Pittsfield, MA

$2,576 - $4,416

Uber

Green Driver($3.3k-$6.1k/Month)-Pittsfield,MA | Hiring

Pittsfield, MA

$3,300 - $6,050

Uber

Uber is hiring a Weekend Driver in Pittsfield | Apply Now

Pittsfield, MA

$2,300 - $4,024

Final Mile Delivery Co.

Independent Contractor Driver-Final Mile Parcel•Pittsfield,MA•Final

Pittsfield, MA

$2,760 - $5,060

Shipt

Weekend Shift:Driver Opportunity-Pittsfield

Pittsfield, MA

$2,500 - $4,500

Midnight Logistics

Late Night Convenience & Grocery Courier needed in Pittsfield(Apply Now)

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 121+ 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 121+ 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

10 open positions

Part-Time Driving Jobs in Pittsfield

6 open positions

Grocery Jobs in Pittsfield

2 open positions

Weekend Driving Jobs in Pittsfield

1 open positions

Last updated: April 26, 2026