Driving Jobs in Annapolis, MD — Apply Today

As of May 2026, there are 40+ open driving positions in Annapolis, MD. Current pay ranges from $864 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.

Grubhub

Part-Time Grubhub Driver (Lunch Rush)

Annapolis, MD

$864 - $1,944

United Parcel Service (UPS)

Immediate Opening in Annapolis for a UPS Package Delivery Driver

Annapolis, MD

$4,000 - $7,500

Secure Document Couriers

Independent Contractor Driver-Night Shift Legal/document Courier

Annapolis, MD

$2,800 - $5,000

National Grocery Delivery Network

Start ASAP:Driver Opportunity(Annapolis)

Annapolis, MD

$2,625 - $4,725

Campus Courier Network

Driver Opportunity needed in Annapolis(Apply Now)

Annapolis, MD

$2,730 - $5,040

Suburban Delivery Network

$46.00/hr Driver Opportunity-Annapolis(PT)

Annapolis, MD

$2,940 - $5,040

Grubhub

Night Shift Grubhub Courier

Annapolis, MD

$2,464 - $4,224

Grubhub

Suburban Route Grubhub Driver

Annapolis, MD

$2,184 - $3,822

Regional Expedite Logistics

Annapolis,MD:Independent Contractor Driver-Long Distance / Regional

Annapolis, MD

$3,500 - $6,000

Grubhub

Grubhub Delivery Driver

Annapolis, MD

$2,875 - $5,175

Auto Logistics Pros

Apply Now:Independent Contractor Driver-Auto Parts Courier in

Annapolis, MD

$2,800 - $4,800

Local Shopper Partners

Courier needed in Annapolis(Apply Now)

Annapolis, MD

$2,000 - $3,500

Driving Jobs in Annapolis — FAQ

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

Last updated: May 04, 2026