Driving Jobs in Annapolis, MD — See Openings

As of September 2026, there are 20+ open driving positions in Annapolis, MD. Current pay ranges from $1,380 to $7,820 per year. Top hiring areas include Delivery Driver and Dsp. New roles are posted daily — listings on this page are verified and updated regularly.

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Annapolis, MD

$3,500 - $6,000

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Annapolis, MD

$2,875 - $5,175

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Annapolis, MD

$2,000 - $4,000

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Annapolis, MD

$4,600 - $7,820

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Annapolis, MD

$2,800 - $5,000

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Annapolis, MD

$2,400 - $4,200

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Annapolis, MD

$3,500 - $6,000

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Annapolis, MD

$2,640 - $4,840

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Annapolis, MD

$2,464 - $4,224

United Parcel Service (UPS)

UPS Package Delivery Driver

Annapolis, MD

$3,520 - $6,600

Domino's Pizza

Pizza Delivery Driver•Annapolis,MD•Domino's Pizza | Hiring

Annapolis, MD

$2,500 - $4,200

Amazon DSP

Apply Now:Delivery Driver in Annapolis,MD | Hiring

Annapolis, MD

$4,024 - $5,520

Driving Jobs in Annapolis — FAQ

How many driving jobs are available in Annapolis, MD right now?
There are currently 20+ open driving positions in Annapolis, MD. 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 Annapolis?
Driving job pay in Annapolis 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 Annapolis?
Yes. Many delivery driver, courier, and DSP positions in Annapolis 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 Annapolis?
Driving jobs in Annapolis 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 Annapolis?
Benefits vary by employer, but many driving positions in Annapolis 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 Annapolis?
Your take-home pay as a driver in Annapolis 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 Annapolis?
Yes, many driving positions in Annapolis 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 20+ listings above and apply directly.

Last updated: September 11, 2026