Chesapeake Charter is currently seeking drivers. Our quality of service is largely due to the professionalism of our drivers. The following are the minimum requirements of all applicants:

  • Maryland Class A or B CDL (with Passenger “P” and School Bus “S” Endorsements (training available at no cost to you)
  • If you do not have a CDL, we will provide training
  • You will need to get a current medical certificate and a pre-employment / random drug and alcohol testing at no cost to you
  • Successful completion of Certification Class
  • Great Attitude – A MUST

You may call our office for an application appointment, or visit our office during normal office hours which are Monday-Friday 9:00 am to 5:00 pm.

Thanks for such great service! Our driver, John was fantastic. We all felt so safe with him at the wheel!” – B. Moran, Severn School

Your drivers were FANTASTIC! Thank you SO much!”– L. Kelly, Bride

The drivers were awesome.”– Wedding Savvy, Annapolis

Our Services

  • Wedding Transportation
  • School Field Trips
  • Church Outings
  • Shuttle Services
  • DC Tours
  • Atlantic City
  • All Events & Occasions

We need Experienced Diesel Technicians!

We are looking for experienced diesel technicians to join our team!


We specialize in repairs to our own fleet of buses, motor coaches and some heavy equipment. Repairs for this position include, but are not limited to:

  • Preventative maintenance
  • Diagnostics
  • Engines
  • Tires
  • Tune-ups
  • Brakes
  • Heat/AC
  • Suspensions
  • Electrical

We have openings for all levels of Diesel Technicians, all levels are encouraged to apply. Successful candidates for the Diesel Technician position will have:

  • 5+ years of experience as a Diesel Technician
  • ASE/Manufacturer certifications preferred
  • Diagnostic ability
  • Ability to be a self starter
  • Troubleshooting skills
  • Commitment to quality
  • Team player
  • Good communicator
  • Valid driver’s license
  • Competitive pay
  • Health, Dental & Vision Insurance
  • Simple IRA with Match
  • Paid Vacation
  • Paid Holidays
  • Provided Trainings
  • Uniforms Provided

If this sounds like you, we would enjoy bringing you in for a tour of the facility. At that time, we would be happy to answer any additional questions. Thank you for your time and consideration.

Careers May 29, 2018