Delivery Driver Jobs in Annapolis, MD — Now Hiring

As of May 2026, there are 39 delivery driver openings in Annapolis, MD. Local pay ranges from $864 to $8,500/year. Listings are updated daily — benefits start Day 1 for most positions.

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

Delivery Driver Jobs in Annapolis — FAQ

How many delivery driver jobs are open in Annapolis, MD?
There are currently 39+ 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 39+ 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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Other Driving Jobs in Annapolis

1 open positions

Last updated: May 04, 2026