Top 13 Municipal Jobs in Chestertown, Md

Street Supervisor
Town of Chestertown —Chestertown, MD
- $70,000 - $85,000 a year
- Construction site
- 5 years
- Mid-level
- Paid holidays
- Health insurance
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10d
Custodian
City of Havre de Grace —Havre de Grace, MD
- $33,627 - $72,904 a year
- Online Application
- High school diploma or GED
- Ability to stand for extended periods
- Entry level
- AD&D insurance
- Paid holidays
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6d
Customer Service Specialist - Finance
City of Aberdeen —Aberdeen, MD
- From $18 an hour
- 18 years or older
- Word processing
- Computer literacy
- Paid holidays
- Disability insurance
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5d
Driver/Laborer I
City of Havre de Grace —Havre de Grace, MD
- $38,064 - $82,368 a year
- Online Application
- Writing skills
- High school diploma or GED
- Ability to lift 50 pounds
- AD&D insurance
- Paid holidays
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Marine Maintenance Worker
City of Havre de Grace —Havre de Grace, MD
- $38,064 - $82,368 a year
- Online Application
- Management
- Ability to walk for extended periods
- Writing skills
- AD&D insurance
- Paid holidays
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10d
Police Communication Officer
City of Havre de Grace —Havre de Grace, MD
- From $49,296 a year
- Weekends as needed
- In person
- Background check
- Writing skills
- English
- AD&D insurance
- Paid holidays
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Wastewater & Water Treatment Plant Senior Operator
City of Havre de Grace —Havre de Grace, MD
- Weekends as needed
- Computer literacy
- Writing skills
- Mid-level
- AD&D insurance
- Paid holidays
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Human Resources Administrator
City of Aberdeen —Aberdeen, MD
- $26 - $31 an hour
- Mid-level
- Office
- 3 years
- Paid holidays
- Disability insurance
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7d
Water Plant Maintenance Supervisor
City of Havre de Grace —Havre de Grace, MD
- $45,656 - $99,112 a year
- Online Application
- Schematics
- Writing skills
- Basic math
- AD&D insurance
- Paid holidays
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Maintenance Work - APG Shop
City of Aberdeen - APG Shop —Aberdeen, MD
- From $20 an hour
- Background check
- Heavy equipment operation
- CDL
- Paid holidays
- Disability insurance
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Maintenance Foreman
City of Aberdeen - APG Shop —Aberdeen, MD
- $29 - $32 an hour
- CDL B
- Background check
- Mid-level
- Paid holidays
- Disability insurance
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municipal jobs near chestertown, md

Street Supervisor

Town of Chestertown
Chestertown, MD

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Job Details

$70,000 - $85,000 a year
10 days ago

Benefits

Paid holidays
Health insurance
Dental insurance
Vision insurance
Life insurance

Qualifications

High school diploma or GED

Full Job Description

Town of Chestertown - Street Supervisor

Job Summary

The Town of Chestertown is seeking an experienced, motivated, and hands-on Street Supervisor to lead the daily operations of the Street Department. This position is responsible for planning, directing, and supervising the maintenance and repair of Town streets, sidewalks, right-of-way, parks, and other public infrastructure. The Street Supervisor leads a dedicated team, manages projects and resources, ensures compliance with safety standards, and helps maintain the high quality of public services that residents rely on.

Essential Responsibilities

Supervise street maintenance, repair, and construction activities to ensure work is completed safely, efficiently, and in accordance with established quality standards.
Conduct field inspections of projects to monitor progress, identify issues, and ensure compliance with safety regulations and Town policies.
Plan, organize, and oversee snow removal operations for Town streets, parks, and public walkways.
Supervise yard waste and bulk trash collection services.
Coordinate staffing and logistics for Town events, including stage setup, barricades, and road closures.
Assist with the preparation, administration, and monitoring of the departmental budget.
Determine staffing requirements and coordinate the procurement and maintenance of equipment, materials, and supplies.
Train, supervise, evaluate, and mentor assigned employees to promote a safe, productive, and collaborative work environment.
Respond to inquiries and concerns from residents, contractors, and other departments, investigating complaints and implementing appropriate corrective actions.
Ensure compliance with all applicable federal, state, and local safety regulations and Town policies.

Qualifications

Demonstrated leadership and supervisory experience.
Ability to communicate effectively with employees, management, elected officials, and the public.
Knowledge of street maintenance, construction practices, traffic control procedures, and workplace safety standards.
Ability to interpret and apply applicable laws, regulations, policies, and procedures.
Ability to conduct on-site inspections and evaluate work quality.
Proficiency with modern office equipment and standard computer software.

Education & Experience

High school diploma or equivalent required.
Minimum of five (5) years of progressively responsible experience in public works, street maintenance, construction, or a related field, including supervisory or management experience.
Commercial Driver's License (CDL) preferred.

Salary Range - $70,000 to $85,000

Benefits include:

Competitive health, dental, and vision insurance
Life insurance
Maryland State Retirement and Pension System
Paid vacation and sick leave
Fourteen (14) paid holidays
Opportunities for professional development and training

Interested candidates should submit a cover letter and resume to Town of Chestertown, Attention: Human Resources, 118 N Cross Street, Chestertown, MD 21620 by August 21, 2026.

For more information about the Town of Chestertown, please visit our website.

The Town of Chestertown is an Equal Employment Opportunity Employer.

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Refine Your Search

municipal jobs in chestertown, md

Street Supervisor

Custodian

Customer Service Specialist - Finance

Driver/Laborer I

Marine Maintenance Worker

Police Communication Officer

Wastewater & Water Treatment Plant Senior Operator

Human Resources Administrator

Water Plant Maintenance Supervisor

Maintenance Work - APG Shop

Maintenance Foreman

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