Driving Jobs in Annapolis, MD — Start This Week

As of May 2026, there are 40+ open driving positions in Annapolis, MD. Current pay ranges from $14 to $135,000 per year. Top hiring areas include Delivery Driver, Cdl Driver and Yard Jockey. New roles are posted daily — listings on this page are verified and updated regularly.

Amazon Flex

Apply Now:Delivery Driver-Independent Contractor in Annapolis

Annapolis, MD

$18 - $25

United Parcel Service (UPS)

UPS Package Delivery Driver-Annapolis,MD | Hiring

Annapolis, MD

$4,000 - $7,500

Matheson Postal Services

Annapolis Job:USPS Mail Haul Truck Driver-CDL A Contractor(Full-time)

Annapolis, MD

$70,000 - $90,000

Regional Expedite Logistics

Regional Expedite Logistics seeks Independent Contractor Driver-Long

Annapolis, MD

$3,500 - $6,000

Grubhub

Annapolis Suburban Delivery Driver with $3k-$4.9k/Month Pay | Hiring

Annapolis, MD

$3,000 - $4,900

Postmates

$2.8k-$4.8k/Month Same-day Delivery Driver job in Annapolis | Hiring

Annapolis, MD

$2,816 - $4,752

Local Merchant Delivery Network

Independent Contractor Driver-Early Morning

Annapolis, MD

$2,400 - $4,200

Roadie

Roadie seeks Big & Bulky Delivery Driver in Annapolis | Hiring

Annapolis, MD

$3,864 - $6,624

Granite Construction

Granite Construction Needs CDL B Water Truck Driver-Construction Site

Annapolis, MD

$26 - $32

Corporate Catering Couriers

Corporate Catering Couriers seeks Independent Contractor

Annapolis, MD

$3,500 - $6,000

GoPuff

Convenience Store Delivery Driver Position in Annapolis | Hiring

Annapolis, MD

$2,800 - $4,500

FedEx Custom Critical

Fedex Custom Critical seeks Expedited Sprinter Van Driver-Time

Annapolis, MD

$75,000 - $135,000

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 13, 2026