Driving Jobs in Ossining, NY — Hiring Now

As of May 2026, there are 50+ open driving positions in Ossining, NY. Current pay ranges from $500 to $8,925 per year. Top hiring areas include Delivery Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

Healthway Logistics

Independent Medical Specimen Courier

Ossining, NY

$3,000 - $5,000

Uber

Flexible Gig:Campus Area Ubereats Driver(Ossining) | Hiring

Ossining, NY

$2,600 - $4,800

Task & Dash Couriers

On-Demand Local Courier (Gig Economy)

Ossining, NY

$2,000 - $4,000

On-Demand Tasks Network

Apply Now:Independent Contractor Driver-On-demand Errands in Ossining

Ossining, NY

$2,000 - $4,000

Heavy Freight Logistics

Independent Contractor Driver-Cargo Van / Box Truck Specialist(Gig

Ossining, NY

$5,250 - $8,925

Uber

Ossining Weekend Driver with $2.3k-$4k/Month Pay | Hiring

Ossining, NY

$2,300 - $4,024

Local Merchant Delivery Network

Ossining Contractor Independent Contractor Driver-Early Morning

Ossining, NY

$2,688 - $4,704

Uber

Ubereats Delivery Driver(Gig Economy And Logistics)Vacancy in Ossining

Ossining, NY

$2,500 - $4,500

Auto Logistics Pros

Work in Ossining:Independent Contractor Driver-Auto Parts Courier

Ossining, NY

$2,576 - $4,416

Local Logistics Network

Independent Contractor Driver-Medical Courier Position in Ossining

Ossining, NY

$3,449 - $5,750

Metro Pedal Express

Urban Bicycle Courier (Downtown Dispatch)

Ossining, NY

$2,500 - $4,000

Local Merchant Delivery Network

Local Merchant Delivery Network(Ossining)Hiring:Independent Contractor

Ossining, NY

$2,400 - $4,200

Driving Jobs in Ossining — FAQ

How many driving jobs are available in Ossining, NY right now?
There are currently 50+ open driving positions in Ossining, NY. 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 Ossining?
Driving job pay in Ossining 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 Ossining?
Yes. Many delivery driver, courier, and DSP positions in Ossining 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 Ossining?
Driving jobs in Ossining 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 Ossining?
Benefits vary by employer, but many driving positions in Ossining 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 Ossining?
Your take-home pay as a driver in Ossining 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 Ossining?
Yes, many driving positions in Ossining 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 50+ listings above and apply directly.

Last updated: May 03, 2026