Driving Jobs in Annapolis, MD — Start This Week - Page 2

Driving companies hiring in Annapolis, MD — 50+ open positions across CDL trucking, delivery, courier & more. Weekly pay, benefits available. Browse openings in Annapolis.

Uber Eats

Earn Extra Cash:Driver Opportunity(Annapolis)

Annapolis, MD

$3,150 - $5,250

Gannett

Newspaper Delivery Driver Position in Annapolis | Hiring

Annapolis, MD

$1,380 - $2,760

Regional Expedite Logistics

Independent Contractor Driver - Long Distance / Regional Courier

Annapolis, MD

$3,500 - $6,000

Auto Logistics Pros

Independent Contractor Driver - Auto Parts Courier

Annapolis, MD

$2,464 - $4,224

Urban Pedal Logistics

Independent Contractor Driver - Urban E-Bike/Scooter Courier

Annapolis, MD

$2,875 - $5,175

United States Postal Service

Annapolis Assistant Rural Carrier with $1.5k-$2.5k/Month Pay | Hiring

Annapolis, MD

$1,500 - $2,500

DoorDash

Flexible Hours:Driver Opportunity-Annapolis

Annapolis, MD

$15 - $22

United States Postal Service

Immediate Start:Commercial Box Truck Mail Courier in Annapolis,MD

Annapolis, MD

$4,000 - $6,000

Express Logistics

Weekend Shift:Driver Opportunity-Annapolis

Annapolis, MD

$19 - $24

Wayfair

Driver Opportunity needed in Annapolis(Apply Now)

Annapolis, MD

$21 - $27

Final Mile Delivery Co.

Independent Contractor Driver - Final Mile Parcel

Annapolis, MD

$2,640 - $4,840

Instacart

Annapolis Needs:Driver Opportunity(Part-Time)

Annapolis, MD

$2,755 - $4,560

Last updated: October 03, 2026