Driving Jobs in Annapolis, MD — See Openings - Page 4

50+ driving jobs in Annapolis, MD hiring now — CDL, delivery driver, courier & more. $18–$90K+, many with benefits. See what's open in Annapolis.

Uber

Apply Now in Annapolis:Ubereats Shop And Pay Expert | Hiring

Annapolis, MD

$2,800 - $4,800

Regional Expedite Logistics

$3.5k-$6k/Month Independent Contractor Driver-Long Distance / Regional

Annapolis, MD

$3,500 - $6,000

Urban Pedal Logistics

Independent Contractor Driver-Urban E-bike/scooter

Annapolis, MD

$2,500 - $4,500

Local Logistics Network

Annapolis:Independent Contractor Driver-Medical Courier

Annapolis, MD

$3,360 - $5,600

Uber

Annapolis Contractor Part-time Driver | Hiring

Annapolis, MD

$500 - $1,500

Local Merchant Delivery Network

$2.4k-$4.2k/Month Independent Contractor Driver-Early Morning

Annapolis, MD

$2,400 - $4,200

Uber

Uberxl Driver(Gig Economy And Transportation)Vacancy in Annapolis

Annapolis, MD

$4,320 - $7,020

Uber

Suburban Route Ubereats Driver Position in Annapolis | Hiring

Annapolis, MD

$2,400 - $4,200

CareDrop Couriers

Pharmacy Delivery Courier (Last-Mile Healthcare)

Annapolis, MD

$3,000 - $4,500

Secure Legal Logistics

Legal & Secure Document Courier

Annapolis, MD

$3,500 - $5,500

Uber

Part-time Ubereats Driver(lunch Rush)-Annapolis,MD | Hiring

Annapolis, MD

$800 - $1,800

Uber

Annapolis-based Weekend Driver Opening | Hiring

Annapolis, MD

$2,000 - $3,500

Last updated: May 03, 2026