Driving Jobs in Pittsfield, MA — Now Hiring

As of May 2026, there are 200+ open driving positions in Pittsfield, MA. Current pay ranges from $440 to $10,000 per year. Top hiring areas include Delivery Driver, General and Part Time. New roles are posted daily — listings on this page are verified and updated regularly.

Morning Express Couriers

Driver Opportunity needed in Pittsfield(Apply Now)

Pittsfield, MA

$2,200 - $3,800

Old Dominion Freight Line

Pittsfield Flexible Role:Old Dominion Linehaul Driver

Pittsfield, MA

$7,000 - $10,000

Lyft

Pittsfield XL Rideshare Driver(Contractor)-Lyft | Hiring

Pittsfield, MA

$4,000 - $6,500

Grubhub

Pittsfield Part-Time:Early Morning Driver(Apply Today) | Part

Pittsfield, MA

$2,200 - $3,800

Textile Transit Co.

Part-Time Job at Textile Transit Co.:Industrial Linen & Laundry

Pittsfield, MA

$4,000 - $5,800

Local Logistics Network

Independent Contractor Driver-Medical Courier Needed-Pittsfield Area

Pittsfield, MA

$3,449 - $5,750

Instacart

Suburban Instacart Shopper

Pittsfield, MA

$2,548 - $4,368

Uber

Night Shift Rideshare Driver Needed-Pittsfield Area | Hiring

Pittsfield, MA

$3,200 - $5,500

Shipt

[Part-Time] Bulk Order Specialist-Pittsfield

Pittsfield, MA

$3,200 - $5,500

Grubhub

Grubhub Delivery Driver

Pittsfield, MA

$2,200 - $3,960

Peak Season Logistics

Flexible Part-Time Seasonal Holiday Package Driver in Pittsfield

Pittsfield, MA

$3,500 - $5,000

ProWear Logistics

Part-Time Uniform & Apparel Route Driver in Pittsfield

Pittsfield, MA

$3,500 - $5,500

Driving Jobs in Pittsfield — FAQ

How many driving jobs are available in Pittsfield, MA right now?
There are currently 200+ 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 200+ listings above and apply directly.

Last updated: May 03, 2026