The Town of Chestertown is accepting applications/resumes for the position of Street Worker II. FT/40 hours per week. Performs a variety of manual labor tasks in the maintenance and repair of streets, parks, and municipal properties. Will operate large trucks, snow plows, lawn mowers (riding & push), weed eaters, blowers, air hammers, chain saws, etc. Knowledge of and operation of heavier equipment such as back hoes, skid loaders, mini-excavators, etc. Digs and backfills ditches by hand or with equipment. Assists in pouring of concrete and repairing potholes. Will use hand tools like shovels, snow shovels, loppers, tree saws and edgers for jobs. Ability to perform manual labor sometimes under unfavorable weather conditions is required. Other duties as required by immediate supervisor.

The Town offers a full package of benefits including medical insurance, vacation, sick leave and pension. A high school diploma is required.  Must have a valid Maryland CDL Driver’s License.

Applications or resumes should be delivered to the Town Hall, 118 N. Cross Street, Chestertown, MD 21620, faxed to 410-778-4378, or emailed to kim@chestertown.com.

Drug testing and a background check is required in the hiring process and random drug testing occurs as part of employment with the Town.

The Town of Chestertown is an Equal Opportunity Employer.


Performs a variety of semi-skilled tasks and operates small and larger equipment in the maintenance and repair of streets, rights-of-way, parks and other Town-owned properties.


(The duties listed below are intended only as illustrations of the various types of work performed.  The omission of specific duties does not exclude them from the work required of the position as long as the work is similar, related, or a logical assignment to the position.)

  • Has a Maryland CDL license to drive and operate larger trucks and snow plows
  • Must be able to operate hand tools, cut off saws, weed eaters, lawn mowers (riding and push), chain saws, blowers, air hammers, etc.;
  • Displays the knowledge of and operation of heavier equipment such as back hoes, skid loaders, mini-excavators, etc.
  • Digs and backfills ditches by hand or with equipment;
  • Shovels snow or plows it with riding lawn mowers or large trucks equipped with plows;
  • Sets out and removes traffic  barricades and cones and flags during street operations;
  • Loads and unloads gravel, dirt, tools, wood, forms and equipment;
  • Erects or replaces street signs and sign posts;
  • Cuts and weed eats grass, cuts and trims trees, rakes leaves, waters and assists in planting and care of trees, shrubs, flowers and grass;
  • Picks up paper and debris in parks, rights-of-way and Town owned properties;
  • Loads dirt and leaves from streets by hand onto a truck or trailer;
  • Removes snow by hand and spreads sand or salt on icy streets and sidewalks;
  • Cleans out storm drains, cleans equipment after use, cleans Town owned properties;
  • Assists in pouring of concrete and repairing pot holes with asphalt paving mix;
  • Performs other related duties as required by their immediate supervisor.



Knowledge of the care and use of standard hand and power tools used in the construction and maintenance of Town owned facilities.  Skill in the use of standard hand and power tools essential to work performed.  Ability to understand and follow specific oral and written instructions.  Ability to perform manual labor for extended periods of time often under unfavorable weather conditions.  Ability to read and write.


High School diploma or GED.  Maryland CDL driver’s license.  Flagging Classes, first aid and safety courses (these can be added upon employment if not in the newly hired field of experience).


Must have the use of sensory skills in order to effectively communicate and interact with other employees and the public through the use of the telephone and personal contact as normally defined by the ability to see, read, talk, hear, handle or feel objects and controls.  Physical capability to effectively use and operate various items of office related equipment such as, but not limited to, a personal computer, calculator, copier and fax machine.  Significant climbing, stooping, kneeling, crouching, reaching, standing, walking, pushing, ability to lift 80 pounds and repetitive motions.




Street Supervisor

FLSA (Fair Labor Standards Act) STATUS:  


Rev. 8/16

The Town of Chestertown assures Equal Employment Opportunities and equal education opportunities for employees as required by Federal and State Orders and Laws.   Reasonable accommodations may be made to enable individuals with disabilities to perform the essential tasks.  This job description is intended to accurately (reflect the position activities and requirements.  However, management and administration reserves the right to modify, add or remove duties and assign other duties as necessary.   It is no intended to be and should not be construed as an all-inclusive list of all the responsibility, skills, or working conditions associated with the position.

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