Driving Jobs in Pittsfield, MA — See Openings

As of May 2026, there are 160+ open driving positions in Pittsfield, MA. Current pay ranges from $13 to $334,880 per year. Top hiring areas include Delivery Driver, Cdl Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

DoorDash

Entry-Level Delivery Driver — No Experience Required

Pittsfield, MA

$2,200 - $3,800

UPS

Package Delivery Driver(Contract)-Pittsfield,MA

Pittsfield, MA

$23 - $30

Old Dominion Freight Line

(Pittsfield)Part-Time:Driver Opportunity

Pittsfield, MA

$80,000 - $95,000

Heavy Freight Logistics

Heavy Freight Logistics is hiring a Independent Contractor

Pittsfield, MA

$5,000 - $8,500

Uber Eats

Immediate Opening in Pittsfield for a E-bike Delivery Driver | Hiring

Pittsfield, MA

$2,400 - $4,200

Urban Pedal Logistics

MA Career:Independent Contractor Driver-Urban E-bike/scooter Courier

Pittsfield, MA

$2,500 - $4,500

Waste Management

Student Friendly:Driver Opportunity(Pittsfield)

Pittsfield, MA

$25 - $33

Local Merchant Delivery Network

Join Local Merchant Delivery Network in Pittsfield as a Independent

Pittsfield, MA

$2,400 - $4,200

Wayfair

Pittsfield Delivery Driver-Furniture And Appliance Home Installation

Pittsfield, MA

$21 - $27

General Beer Northeast

Pittsfield Part-Time Job:Beer Delivery Driver-CDL A Distributor

Pittsfield, MA

$25 - $32

Liberty Coca-Cola Beverages

Coca-Cola Driver Merchandiser Delivery Driver

Pittsfield, MA

$23 - $29

IEW Construction

CDL A Truck Driver - Local Lowboy Heavy Haul

Pittsfield, MA

$32 - $38

Driving Jobs in Pittsfield — FAQ

How many driving jobs are available in Pittsfield, MA right now?
There are currently 160+ 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 160+ listings above and apply directly.

Last updated: May 13, 2026