Driving Jobs in Pittsfield, MA — Immediate Openings

As of April 2026, there are 230+ open driving positions in Pittsfield, MA. Current pay ranges from $425 to $10,000 per year. Top hiring areas include Delivery Driver, General and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

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

On-Demand Tasks Network

On-demand Tasks Network(Pittsfield)Hiring:Independent Contractor

Pittsfield, MA

$1,760 - $3,520

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

Local Merchant Delivery Network

Early Morning Bakery/floral(Contract)-Pittsfield | Hiring

Pittsfield, MA

$2,688 - $4,704

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

DoorDash

DoorDash Shop & Deliver Expert (Grocery/Retail)

Pittsfield, MA

$2,576 - $4,416

Driving Jobs in Pittsfield — FAQ

How many driving jobs are available in Pittsfield, MA right now?
There are currently 230+ open driving positions in Pittsfield, MA. These include delivery drivers, CDL truck drivers, couriers, bus drivers, DSP drivers, and local route positions. New jobs are added daily.
How much do driving jobs pay in Pittsfield?
Driving job pay in Pittsfield varies by role: Delivery drivers earn $18–$25/hr, CDL truck drivers $55K–$90K+/year, couriers $16–$22/hr, and bus drivers $20–$30/hr. Night and weekend routes often pay premium rates.
Can I get a driving job with no experience in Pittsfield?
Yes. Many delivery driver, courier, and DSP positions in Pittsfield require no prior experience and provide paid training. Delivery driver positions require a valid driver's license but no CDL. Some carriers offer free CDL training programs.
What schedules do driving jobs offer in Pittsfield?
Driving jobs in Pittsfield offer flexible schedules: day routes (6 AM–4 PM), evening routes (1 PM–10 PM), overnight/line haul (6 PM–6 AM), and weekend-only schedules (Fri–Sun or Sat–Mon). Part-time and gig-style shifts are also available. Overnight and weekend routes typically pay premium rates.
What benefits do driving jobs offer in Pittsfield?
Benefits vary by employer, but many driving positions in Pittsfield offer: health, dental, and vision insurance; 401(k) or retirement plans; paid time off; sign-on bonuses; weekly or daily pay; company-provided vehicles for delivery positions; and CDL training assistance from select employers.
How much do drivers take home after taxes in Pittsfield?
Your take-home pay as a driver in Pittsfield depends on your pay rate, hours worked, and state tax rate. For example, a delivery driver earning $22/hr in a no-tax state like Texas takes home about $750/week, while in California it's closer to $670/week after state tax.
Are driving companies hiring immediately in Pittsfield?
Yes, many driving positions in Pittsfield are hiring immediately with start dates within 1–2 weeks of applying. Delivery driver and courier roles often offer same-week start dates. Browse the 230+ listings above and apply directly.

Last updated: April 17, 2026