Delivery Driver Jobs in Annapolis, MD — Start This Week

As of May 2026, there are 30 delivery driver openings in Annapolis, MD. Local pay ranges from $14 to $135,000/year. Listings are updated daily — benefits start Day 1 for most positions.

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

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

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

Shipt

Pharmacy Delivery Driver•Annapolis,MD•Shipt | Hiring

Annapolis, MD

$3,410 - $5,720

Uber Eats

Join Team:Alcohol Delivery Driver in Annapolis,MD | Hiring

Annapolis, MD

$3,360 - $5,600

Delivery Driver Jobs in Annapolis — FAQ

How many delivery driver jobs are open in Annapolis, MD?
There are currently 30+ 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 30+ 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

Cdl Driver Jobs in Annapolis

9 open positions

Yard Jockey Jobs in Annapolis

1 open positions

Last updated: May 13, 2026