Driving Jobs in Annapolis, MD — See Openings

As of May 2026, there are 50+ open driving positions in Annapolis, MD. Current pay ranges from $500 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.

Mechanic's Choice Transport

Automotive Parts Courier

Annapolis, MD

$2,800 - $4,200

Uber

Annapolis Weekend Ubereats Delivery Professional with

Annapolis, MD

$2,200 - $3,800

Urban Pedal Logistics

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

Annapolis, MD

$2,500 - $4,500

Auto Logistics Pros

Independent Contractor Driver-Auto Parts Courier Needed-Annapolis Area

Annapolis, MD

$2,800 - $4,800

Final Mile Delivery Co.

Independent Contractor Driver-Final Mile Parcel-Annapolis,MD | Hiring

Annapolis, MD

$3,000 - $5,500

Uber

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

Annapolis, MD

$2,940 - $5,250

Secure Document Couriers

Apply Now:Independent Contractor Driver-Night Shift Legal/document

Annapolis, MD

$2,800 - $5,000

United Parcel Service (UPS)

United Parcel Service(UPS)seeks UPS Package Delivery Driver in

Annapolis, MD

$4,000 - $7,500

Metro Pedal Express

Urban Bicycle Courier (Downtown Dispatch)

Annapolis, MD

$2,500 - $4,000

Night Owl Expedite

Overnight Regional Expedite Courier (Hot Shot)

Annapolis, MD

$3,800 - $5,800

Heavy Freight Logistics

Join Heavy Freight Logistics in Annapolis as a Independent Contractor

Annapolis, MD

$4,250 - $7,225

Uber

Annapolis Job:Campus Area Ubereats Driver(Contractor) | Hiring

Annapolis, MD

$2,600 - $4,800

Driving Jobs in Annapolis — FAQ

How many driving jobs are available in Annapolis, MD right now?
There are currently 50+ 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 50+ listings above and apply directly.

Last updated: May 03, 2026