Delivery Driver Jobs in Pittsfield, MA — Start This Week

As of April 2026, there are 187 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.

Bimbo Bakeries USA

Bimbo Bakeries Box Truck Route Driver

Pittsfield, MA

$4,000 - $5,500

Mobile Tool Networks

Pittsfield Job:Mobile Tool Sales Route Driver(Part-Time)

Pittsfield, MA

$4,500 - $8,000

Local Logistics Network

Independent Contractor Driver-Medical Courier•Pittsfield,MA•Local

Pittsfield, MA

$3,000 - $5,000

CareDrop Couriers

Pharmacy Delivery Courier (Last-Mile Healthcare)

Pittsfield, MA

$3,000 - $4,500

Postal Transport Network

Local Mail Transport & Logistics Driver

Pittsfield, MA

$3,458 - $5,005

Grubhub

Night Shift Grubhub Courier

Pittsfield, MA

$2,464 - $4,224

Uber

Pittsfield Job:Part-time Ubereats Driver(lunch Rush)(Contractor)

Pittsfield, MA

$800 - $1,800

Night Owl Expedite

Overnight Regional Expedite Courier (Hot Shot)

Pittsfield, MA

$3,990 - $6,090

Urban Pedal Logistics

Pittsfield-based Independent Contractor Driver-Urban E-bike/scooter

Pittsfield, MA

$2,500 - $4,500

Uber

Join Uber in Pittsfield as a WAV Driver | Hiring

Pittsfield, MA

$3,500 - $5,500

Grubhub

Suburban Route Grubhub Driver

Pittsfield, MA

$2,688 - $4,704

United Parcel Service (UPS)

Pittsfield Job:Driver Opportunity(No Exp Req*)

Pittsfield, MA

$4,500 - $8,000

Delivery Driver Jobs in Pittsfield — FAQ

How many delivery driver jobs are open in Pittsfield, MA?
There are currently 187+ 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 187+ 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

17 open positions

Cdl Driver Jobs in Pittsfield

11 open positions

Part-Time Driving Jobs in Pittsfield

5 open positions

DSP Driver Jobs in Pittsfield

3 open positions

Grocery Jobs in Pittsfield

3 open positions

Weekend Driving Jobs in Pittsfield

2 open positions

Warehouse Jobs in Pittsfield

1 open positions

Overnight Driving Jobs in Pittsfield

1 open positions

Last updated: April 17, 2026