Driving Jobs in Ossining, NY — Open Positions

As of May 2026, there are 40+ open driving positions in Ossining, NY. Current pay ranges from $896 to $8,500 per year. Top hiring areas include Delivery Driver and General. New roles are posted daily — listings on this page are verified and updated regularly.

FreshDrop Logistics

$49.00/hr Driver Opportunity-Ossining(PT)

Ossining, NY

$3,000 - $5,500

Corporate Catering Couriers

Ossining Independent Contractor Driver-Catering Logistics with

Ossining, NY

$3,500 - $6,000

Urban Pedal Logistics

Earn Extra Cash:Courier(Ossining)

Ossining, NY

$2,500 - $4,500

Grubhub

Early Morning Grubhub Driver

Ossining, NY

$2,420 - $4,180

On-Demand Tasks Network

Independent Contractor Driver-On-demand Errands-Ossining,NY | Hiring

Ossining, NY

$2,000 - $4,000

Grubhub

Night Shift Grubhub Courier

Ossining, NY

$3,219 - $5,520

Morning Express Couriers

Flexible Hours:Driver Opportunity-Ossining

Ossining, NY

$2,310 - $3,990

Midnight Logistics

Earn Extra Cash:Late Night Convenience & Grocery Courier(Ossining)

Ossining, NY

$2,800 - $4,800

Grubhub

Part-Time Grubhub Driver (Lunch Rush)

Ossining, NY

$896 - $2,016

Urban Pedal Logistics

Immediate Opening in Ossining for a Independent Contractor

Ossining, NY

$2,500 - $4,500

Heavy Freight Logistics

$5k-$8.5k/Month Independent Contractor Driver-Cargo Van / Box Truck

Ossining, NY

$5,000 - $8,500

United Parcel Service (UPS)

Join United Parcel Service(UPS)in Ossining as a UPS Package Delivery

Ossining, NY

$4,000 - $7,500

Driving Jobs in Ossining — FAQ

How many driving jobs are available in Ossining, NY right now?
There are currently 40+ 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 40+ listings above and apply directly.

Last updated: May 04, 2026