Driving Jobs in Pittsfield, MA — Apply Today

As of May 2026, there are 240+ open driving positions in Pittsfield, MA. Current pay ranges from $440 to $10,000 per year. Top hiring areas include Delivery Driver, General and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

Uber

Uber is hiring a WAV Driver in Pittsfield | Apply Now

Pittsfield, MA

$3,500 - $5,500

Grubhub

Suburban Route Grubhub Driver

Pittsfield, MA

$2,184 - $3,822

Health Transit Logistics

Part-Time Job in Pittsfield – Medical & Pharmacy Package Courier

Pittsfield, MA

$3,200 - $4,500

Sysco Corporation

Sysco Foodservice Box Truck Driver

Pittsfield, MA

$5,940 - $9,180

Uber

Uber Needs Ubereats Delivery Driver in Pittsfield | Hiring

Pittsfield, MA

$2,500 - $4,500

Uber

WAV Rideshare Driver($3.5k-$5.5k/Month)-Pittsfield,MA | Hiring

Pittsfield, MA

$3,500 - $5,500

SnackRoute Solutions

Weekend Shift:Driver Opportunity-Pittsfield

Pittsfield, MA

$3,360 - $5,040

United States Postal Service

Assistant Rural Carrier (Weekend & Holiday Delivery)

Pittsfield, MA

$1,620 - $2,700

Nightline Freight

Part-Time Overnight Parcel Transfer Driver – Pittsfield

Pittsfield, MA

$4,140 - $5,979

SnackRoute Solutions

Urgent Part-Time:Vending & Micro-market Route Driver(Pittsfield)

Pittsfield, MA

$3,000 - $4,500

United States Postal Service

Commercial Box Truck Mail Courier (MVO)

Pittsfield, MA

$3,400 - $5,100

Local Logistics Pros

Part-Time Local Package Delivery Driver – Pittsfield(Hiring)

Pittsfield, MA

$3,000 - $4,500

Driving Jobs in Pittsfield — FAQ

How many driving jobs are available in Pittsfield, MA right now?
There are currently 240+ 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 240+ listings above and apply directly.

Last updated: May 08, 2026