Driving Jobs in Pittsfield, MA — Now Hiring

As of April 2026, there are 140+ open driving positions in Pittsfield, MA. Current pay ranges from $425 to $9,520 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.

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Pittsfield, MA

$2,940 - $5,040

Regional Expedite Logistics

Regional Expedite Logistics is hiring a Independent Contractor

Pittsfield, MA

$3,500 - $6,000

Uber

Flexible Gig:Night Shift Ubereats Courier(Pittsfield) | Hiring

Pittsfield, MA

$2,800 - $4,800

Wholesale Transit Partners

Start ASAP:Driver Opportunity(Pittsfield)

Pittsfield, MA

$3,040 - $5,225

Instacart

Suburban Instacart Shopper

Pittsfield, MA

$3,080 - $5,280

Instacart

Weekend Instacart Shopper

Pittsfield, MA

$1,700 - $2,975

DoorDash

DoorDash Delivery Driver (Dasher)

Pittsfield, MA

$2,200 - $3,960

DoorDash

DoorDash Shop & Deliver Expert (Grocery/Retail)

Pittsfield, MA

$3,024 - $5,184

Auto Logistics Pros

Auto Logistics Pros Needs Independent Contractor Driver-Auto Parts

Pittsfield, MA

$2,800 - $4,800

Instacart

Early Morning Instacart Shopper

Pittsfield, MA

$2,024 - $3,496

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Pittsfield, MA

$3,500 - $6,000

Auto Logistics Pros

Independent Contractor Driver-Auto Parts

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 140+ 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 140+ listings above and apply directly.

Last updated: April 26, 2026