Driving Jobs in Pittsfield, MA — Start This Week

As of May 2026, there are 180+ open driving positions in Pittsfield, MA. Current pay ranges from $425 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.

Shipt

Weekend Shift:Driver Opportunity-Pittsfield

Pittsfield, MA

$2,500 - $4,500

Uber

Part-time Driver-Pittsfield,MA | Hiring

Pittsfield, MA

$425 - $1,275

Instacart

Dedicated Instacart Shopper & Driver

Pittsfield, MA

$3,000 - $5,500

Uber

Join Uber in Pittsfield as a Night Shift Rideshare Driver | Hiring

Pittsfield, MA

$3,200 - $5,500

Grubhub

Pittsfield Part-Time:Part-time Driver(lunch Rush)(Hiring) | Part

Pittsfield, MA

$800 - $1,800

DoorDash

DoorDash Large Order (Catering) Driver

Pittsfield, MA

$3,780 - $6,480

Uber

$2.5k-$4.5k/Month Ubereats Bicycle & Scooter Courier job in Pittsfield

Pittsfield, MA

$2,500 - $4,500

Local Merchant Delivery Network

Pittsfield Independent Contractor Driver-Early Morning Bakery/floral

Pittsfield, MA

$2,400 - $4,200

Uber

Uber(Pittsfield)Hiring:EV Rideshare Driver | Apply Now

Pittsfield, MA

$3,000 - $5,500

Regional Expedite Logistics

Regional Expedite Logistics is hiring a Independent Contractor

Pittsfield, MA

$3,500 - $6,000

PepsiCo

Pittsfield Contract:Route Sales Delivery Driver

Pittsfield, MA

$4,500 - $7,000

Grubhub

Part-Time Suburban Route Driver at Grubhub – Pittsfield | Part

Pittsfield, MA

$2,400 - $4,200

Driving Jobs in Pittsfield — FAQ

How many driving jobs are available in Pittsfield, MA right now?
There are currently 180+ 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 180+ listings above and apply directly.

Last updated: May 04, 2026