Delivery Driver Jobs in Pittsfield, MA — See Openings

As of May 2026, there are 152 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.

Shipt

Weekend Shift:Driver Opportunity-Pittsfield

Pittsfield, MA

$2,500 - $4,500

Uber

Part-time Driver-Pittsfield,MA | Hiring

Pittsfield, MA

$425 - $1,275

Instacart

Dedicated Instacart Shopper & Driver

Pittsfield, MA

$3,000 - $5,500

Uber

Join Uber in Pittsfield as a Night Shift Rideshare Driver | Hiring

Pittsfield, MA

$3,200 - $5,500

Grubhub

Pittsfield Part-Time:Part-time Driver(lunch Rush)(Hiring) | Part

Pittsfield, MA

$800 - $1,800

DoorDash

DoorDash Large Order (Catering) Driver

Pittsfield, MA

$3,780 - $6,480

Uber

$2.5k-$4.5k/Month Ubereats Bicycle & Scooter Courier job in Pittsfield

Pittsfield, MA

$2,500 - $4,500

Local Merchant Delivery Network

Pittsfield Independent Contractor Driver-Early Morning Bakery/floral

Pittsfield, MA

$2,400 - $4,200

Uber

Uber(Pittsfield)Hiring:EV Rideshare Driver | Apply Now

Pittsfield, MA

$3,000 - $5,500

PepsiCo

Pittsfield Contract:Route Sales Delivery Driver

Pittsfield, MA

$4,500 - $7,000

Grubhub

Part-Time Suburban Route Driver at Grubhub – Pittsfield | Part

Pittsfield, MA

$2,400 - $4,200

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Pittsfield, MA

$2,800 - $5,040

Delivery Driver Jobs in Pittsfield — FAQ

How many delivery driver jobs are open in Pittsfield, MA?
There are currently 152+ 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 152+ 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

7 open positions

Cdl Driver Jobs in Pittsfield

3 open positions

Grocery Jobs in Pittsfield

2 open positions

Weekend Driving Jobs in Pittsfield

1 open positions

DSP Driver Jobs in Pittsfield

1 open positions

Last updated: May 04, 2026