Driving Jobs in Pittsfield, MA — Start This Week

As of May 2026, there are 50+ open driving positions in Pittsfield, MA. Current pay ranges from $14 to $85,000 per year. Top hiring areas include Delivery Driver, Cdl Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

FedEx Ground

Pittsfield Career:Delivery Driver-Package Handler at Fedex Ground

Pittsfield, MA

$21 - $26

Domino's Pizza

Pittsfield Flexible Job:Delivery Driver-Pizza Delivery Tips Plus Wages

Pittsfield, MA

$14 - $20

Wayfair

$21-$27/hr Delivery Driver-Furniture And Appliance Home Installation

Pittsfield, MA

$21 - $27

Quest Diagnostics

Immediate Opening in Pittsfield for a Delivery Driver-Medical Courier

Pittsfield, MA

$20 - $26

XPO Logistics

Immediate Opening in Pittsfield for a Delivery Driver-Package Handler

Pittsfield, MA

$22 - $28

Instacart

Immediate Opening in Pittsfield for a Delivery Driver-Grocery Same Day

Pittsfield, MA

$16 - $23

Schneider National

Schneider National seeks Delivery Driver-CDL Class A Regional Routes

Pittsfield, MA

$70,000 - $85,000

DoorDash

Immediate Opening in Pittsfield for a Delivery Driver-Food Delivery

Pittsfield, MA

$15 - $22

Amazon Flex

Delivery Driver-Independent Contractor(Contract)-Pittsfield | Hiring

Pittsfield, MA

$18 - $25

Express Logistics

Flexible Gig:Delivery Driver-Full Time Local Routes(Pittsfield)

Pittsfield, MA

$19 - $24

Roadie

Box Truck Delivery Driver

Pittsfield, MA

$4,500 - $7,800

Uber Eats

Daily Pay Delivery Driver

Pittsfield, MA

$3,219 - $5,520

Driving Jobs in Pittsfield — FAQ

How many driving jobs are available in Pittsfield, MA right now?
There are currently 50+ 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 50+ listings above and apply directly.

Last updated: May 10, 2026