Driving Jobs in Pittsfield, MA — See Openings

As of October 2026, there are 250+ open driving positions in Pittsfield, MA. Current pay ranges from $12 to $364,000 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.

XPO Logistics

Evening Role:Driver Opportunity(Pittsfield)

Pittsfield, MA

$22 - $28

Penske Logistics

CDL A Yard Hostler Truck Driver - Trailer Spotter

Pittsfield, MA

$27 - $34

US Postal Service Contractors

Pittsfield Career:Highway Contract Route(HCR)Driver at US Postal

Pittsfield, MA

$4,000 - $7,000

PepsiCo Beverages North America

Immediate Part-Time Pepsi Beverage Delivery Driver-CDL A Job –

Pittsfield, MA

$21 - $29

E-Comm Transit Solutions

Courier(Part-Time)@ E-comm Transit Solutions-Pittsfield

Pittsfield, MA

$3,200 - $4,800

Uber Eats

Daily Pay Delivery Driver Position in Pittsfield | Hiring

Pittsfield, MA

$3,136 - $5,376

United States Postal Service

$3k-$5.5k/Month Seasonal Postal Delivery Worker job in Pittsfield

Pittsfield, MA

$3,000 - $5,500

Postal Transport Network

Pittsfield Local Mail Transport & Logistics Driver with

Pittsfield, MA

$3,800 - $5,500

Amazon AMXL Delivery Partners

Pittsfield Contract:Amazon AMXL Box Truck Delivery Driver

Pittsfield, MA

$4,200 - $5,800

Canteen

Vending Machine Delivery Driver and Route Service

Pittsfield, MA

$18 - $24

Lyft

Now Hiring Pittsfield:Delivery Driver-Rideshare And Package(PT)

Pittsfield, MA

$15 - $24

Uber Eats

Pittsfield Career:Premium Delivery Driver at Uber Eats | Hiring

Pittsfield, MA

$4,500 - $7,000

Driving Jobs in Pittsfield — FAQ

How many driving jobs are available in Pittsfield, MA right now?
There are currently 250+ 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 250+ listings above and apply directly.

Last updated: October 03, 2026