Delivery Driver Jobs in Annapolis, MD — Start This Week

As of September 2026, there are 19 delivery driver openings in Annapolis, MD. Local pay ranges from $1,380 to $7,820/year. Listings are updated daily — benefits start Day 1 for most positions.

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Annapolis, MD

$3,500 - $6,000

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Annapolis, MD

$2,875 - $5,175

On-Demand Tasks Network

Independent Contractor Driver - On-Demand Errands (TaskRabbit/Roadie)

Annapolis, MD

$2,000 - $4,000

Heavy Freight Logistics

Independent Contractor Driver - Cargo Van / Box Truck Specialist

Annapolis, MD

$4,600 - $7,820

Secure Document Couriers

Independent Contractor Driver - Night Shift Legal/Document Courier

Annapolis, MD

$2,800 - $5,000

Local Merchant Delivery Network

Independent Contractor Driver - Early Morning Bakery/Floral

Annapolis, MD

$2,400 - $4,200

Corporate Catering Couriers

Independent Contractor Driver - Catering Logistics

Annapolis, MD

$3,500 - $6,000

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Annapolis, MD

$2,640 - $4,840

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Annapolis, MD

$2,464 - $4,224

United Parcel Service (UPS)

UPS Package Delivery Driver

Annapolis, MD

$3,520 - $6,600

Domino's Pizza

Pizza Delivery Driver•Annapolis,MD•Domino's Pizza | Hiring

Annapolis, MD

$2,500 - $4,200

FedEx Ground

Delivery Driver Position in Annapolis | Hiring

Annapolis, MD

$3,800 - $5,200

Delivery Driver Jobs in Annapolis — FAQ

How many delivery driver jobs are open in Annapolis, MD?
There are currently 19+ delivery driver positions in Annapolis, MD. New delivery driver roles are added regularly — check this page for the latest openings.
How much do delivery driver jobs pay in Annapolis?
Delivery Driver pay in Annapolis varies by employer, route type, and experience level. Many positions offer shift differentials, mileage bonuses, and sign-on bonuses. Browse the listings above to see pay details for each opening.
Do delivery driver jobs in Annapolis require experience?
Many delivery driver positions in Annapolis welcome entry-level applicants. Employers like Amazon, FedEx, and UPS often provide paid training. CDL positions may require a valid commercial license — check individual listings for specific requirements.
How do I apply for delivery driver jobs in Annapolis?
Browse the 19+ delivery driver listings above, click on any position for full details including pay, schedule, and requirements, then follow the application link. Most driving positions have a simple online application.

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1 open positions

Last updated: September 11, 2026