Driving Jobs in Annapolis, MD — Start This Week

As of October 2026, there are 50+ open driving positions in Annapolis, MD. Current pay ranges from $14 to $85,000 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.

Shipt

Weekend Shift:Driver Opportunity-Annapolis

Annapolis, MD

$3,100 - $5,200

United Parcel Service (UPS)

UPS Package Delivery Driver

Annapolis, MD

$3,520 - $6,600

Instacart

Evening Role:Driver Opportunity(Annapolis)

Annapolis, MD

$16 - $23

FedEx Ground

Urgent Hire in Annapolis:Driver Opportunity

Annapolis, MD

$21 - $26

DoorDash

Weekend Shift:Driver Opportunity-Annapolis

Annapolis, MD

$2,700 - $4,600

United States Postal Service

Class A CDL Tractor Trailer Operator-USPS-Annapolis,MD | Hiring

Annapolis, MD

$5,500 - $8,000

Roadie

$4.5k-$7.8k/Month Box Truck Delivery Driver job in Annapolis | Hiring

Annapolis, MD

$4,500 - $7,800

United States Postal Service

Neighborhood Postal Carrier-Annapolis,MD | Hiring

Annapolis, MD

$3,600 - $5,500

United States Postal Service

Seasonal Postal Delivery Worker Position in Annapolis | Hiring

Annapolis, MD

$3,000 - $5,500

United States Postal Service

United States Postal Service Needs Rural Carrier Associate(RCA)in

Annapolis, MD

$3,400 - $4,800

Postmates

Annapolis Job:Driver Opportunity(No Exp Req*)

Annapolis, MD

$3,200 - $5,400

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 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: October 03, 2026