Driving Jobs in Annapolis, MD — Hiring Now

As of May 2026, there are 60+ open driving positions in Annapolis, MD. Current pay ranges from $500 to $8,500 per year. Top hiring areas include Delivery Driver, General and Cdl Driver. New roles are posted daily — listings on this page are verified and updated regularly.

On-Demand Tasks Network

Annapolis Contractor Independent Contractor Driver-On-demand Errands

Annapolis, MD

$2,300 - $4,600

Final Mile Delivery Co.

Independent Contractor Driver-Final Mile Parcel Needed-Annapolis Area

Annapolis, MD

$3,150 - $5,775

Uber

Work in Annapolis:Night Shift Ubereats Courier | Hiring

Annapolis, MD

$2,800 - $4,800

Uber

Event Driver($2.9k-$5.2k/Month)-Annapolis,MD | Hiring

Annapolis, MD

$2,940 - $5,250

Metro Pedal Express

Urban Bicycle Courier (Downtown Dispatch)

Annapolis, MD

$2,500 - $4,000

LKQ Corporation

Apply Now:LKQ Heavy Duty Auto Parts Box Truck Driver in Annapolis

Annapolis, MD

$4,200 - $6,500

Urban Pedal Logistics

Join Team:Independent Contractor Driver-Urban E-bike/scooter Courier

Annapolis, MD

$2,500 - $4,500

Carquest Auto Parts

Annapolis Job:Carquest Regional Parts Transfer Driver(Full-time)

Annapolis, MD

$3,400 - $5,000

Uber

Uber is hiring a Connect Package Delivery Driver in Annapolis

Annapolis, MD

$3,000 - $5,500

Uber

Green Driver•Annapolis,MD•Uber | Hiring

Annapolis, MD

$3,000 - $5,500

Regional Expedite Logistics

Annapolis Contractor Independent Contractor Driver-Long Distance /

Annapolis, MD

$3,185 - $5,460

Heavy Route Couriers

Dedicated Route Freight Courier (Cargo Van)

Annapolis, MD

$4,000 - $6,000

Driving Jobs in Annapolis — FAQ

How many driving jobs are available in Annapolis, MD right now?
There are currently 60+ 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 60+ listings above and apply directly.

Last updated: May 08, 2026