Delivery Driver Jobs in Pittsfield, MA — Hiring Now

As of March 2026, there are 86 delivery driver openings in Pittsfield, MA. Local pay ranges from $500 to $7,500/year. Listings are updated daily — benefits start Day 1 for most positions.

Midday Logistics Co.

Earn Extra Cash:Driver Opportunity(Pittsfield)

Pittsfield, MA

$1,000 - $2,000

Uber

Pittsfield Contractor Rideshare Driver | Hiring

Pittsfield, MA

$3,000 - $5,000

Urban Pedal Logistics

Weekend Shift:Courier-Pittsfield

Pittsfield, MA

$2,500 - $4,500

Grubhub

Part-Time Grubhub Driver (Lunch Rush)

Pittsfield, MA

$896 - $2,016

Uber

Ubereats Delivery Driver(Gig)-Pittsfield

Pittsfield, MA

$2,500 - $4,500

Grubhub

Student-Friendly Part-Time Campus Area Driver in Pittsfield

Pittsfield, MA

$2,600 - $4,800

Uber

Flexible Gig:Ubereats Bicycle & Scooter Courier(Pittsfield) | Hiring

Pittsfield, MA

$2,500 - $4,500

Grubhub

Part-Time Shop And Pay Driver – Pittsfield MA | Part Time Job

Pittsfield, MA

$2,800 - $4,800

DoorDash

Suburban Route DoorDash Driver

Pittsfield, MA

$2,592 - $4,536

Uber

Now Hiring in Pittsfield:Night Shift Ubereats Courier | Apply Now

Pittsfield, MA

$2,800 - $4,800

Uber

Ubereats Bicycle & Scooter Courier(Gig)-Pittsfield

Pittsfield, MA

$2,500 - $4,500

Grubhub

Night Shift Grubhub Courier

Pittsfield, MA

$2,464 - $4,224

Delivery Driver Jobs in Pittsfield — FAQ

How many delivery driver jobs are open in Pittsfield, MA?
There are currently 86+ 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 86+ 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

8 open positions

Part-Time Driving Jobs in Pittsfield

2 open positions

Weekend Driving Jobs in Pittsfield

2 open positions

Grocery Jobs in Pittsfield

1 open positions

Warehouse Jobs in Pittsfield

1 open positions

Last updated: March 15, 2026