Driving Jobs in Pittsfield, MA — Immediate Openings

As of March 2026, there are 80+ open driving positions in Pittsfield, MA. Current pay ranges from $500 to $7,500 per year. Top hiring areas include Delivery Driver, General and Grocery. New roles are posted daily — listings on this page are verified and updated regularly.

National Grocery Delivery Network

Student Friendly:Driver Opportunity(Pittsfield)

Pittsfield, MA

$2,500 - $4,500

FreshDrop Logistics

$49.00/hr Driver Opportunity-Pittsfield(PT)

Pittsfield, MA

$3,000 - $5,500

Local Shopper Partners

Courier(Part-Time)@ Local Shopper Partners-Pittsfield

Pittsfield, MA

$2,100 - $3,675

Suburban Delivery Network

Weekend Shift:Driver Opportunity-Pittsfield

Pittsfield, MA

$2,800 - $4,800

Morning Express Couriers

Flexible Hours:Driver Opportunity-Pittsfield

Pittsfield, MA

$2,310 - $3,990

Midnight Logistics

Late Night Convenience & Grocery Courier needed in Pittsfield(Apply Now)

Pittsfield, MA

$2,800 - $4,800

Wholesale Transit Partners

$50.25/hr Driver Opportunity-Pittsfield(PT)

Pittsfield, MA

$3,200 - $5,500

Midday Logistics Co.

Earn Extra Cash:Driver Opportunity(Pittsfield)

Pittsfield, MA

$1,000 - $2,000

Urban Pedal Logistics

Weekend Shift:Courier-Pittsfield

Pittsfield, MA

$2,500 - $4,500

Campus Courier Network

$44.75/hr Driver Opportunity-Pittsfield(PT)

Pittsfield, MA

$2,730 - $5,040

Grubhub

Part-Time Early Morning Driver at Grubhub – Pittsfield | Part

Pittsfield, MA

$2,200 - $3,800

Grubhub

Student-Friendly Part-Time Campus Area Driver in Pittsfield

Pittsfield, MA

$2,600 - $4,800

Driving Jobs in Pittsfield — FAQ

How many driving jobs are available in Pittsfield, MA right now?
There are currently 80+ 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 80+ listings above and apply directly.

Last updated: March 13, 2026