Chestertown Historic District · Photo: Acroterion · CC BY-SA 4.0How is Chestertown run?
Chestertown’s town government spent $5.9 million on day-to-day services in the year to June 30, 2024, about $1,069 per resident. Water and other utilities ($1.3 million) are counted separately.
What stands out about how Chestertown is run
Read from the town’s budget and official records.
About $1,069 per resident a year, or $2.93 a day
Day-to-day services only. The biggest line: sewer & trash, at 26%.
Thank you for being a neighbor
$1,031 per resident in 2022, close to the middle of similar cities
Chestertown’s day-to-day spending in 2022 ($1,031 per resident, hospital and utilities left out) against 37 Maryland cities of 2,500–9,999 that don’t run their own schools: the median was $906, and the middle half spent $721–$1,266. Chestertown spent more than 62% of them.
Includes sewer and trash ($1.4 million), as the Census Bureau counts them. Later years come from a Census sample, so the comparison stays on 2022. How Town Hall compares budgets →
Maryland cities of 2,500–9,999 that don’t run their own schools, 2022 Census of Governments (every government counted that year; Chestertown itself left out).
Day-to-day spending is up 15% since 2022
Day-to-day services, in dollars, in the years Chestertown reported to the Census Bureau. Prices rose too: about 4% a year in 2022–2024.
Day-to-day spending by fiscal year
Per resident: 2022: $1,031 · 2023: $1,017 · 2024: $1,069. Per resident it went from $1,031 to $1,069 (up 4%), partly because the Census population behind it changed from 5,001 to 5,563.
full-time in March 2025, up from 29 in 2022.
Building projects, interest and enterprises (hospital, utilities) are left out, so a big construction year doesn’t read as growth.
The typical homeowner pays $3,966 a year
Every local property tax on the home: town, schools and county. About 1.15% of the home’s value, vs 0.97% across Maryland.
Typical yearly bill next door and statewide
The Housing page’s calculator splits a monthly payment into loan, tax and insurance at Chestertown’s rate.
Can I afford it? →The median bill homeowners report to the Census survey (bills of $10,000+ are reported as “$10,000+”). The effective rate is that bill ÷ the median home value: a rough guide, not the official tax rate.
Tax bills are one input to Chestertown’s Cost of living grade. Cost of living in Chestertown →
Who’s in charge in Chestertown
Names change after every election, so we link to the source that keeps them current.
Chestertown’s meeting calendar isn’t in our feed yet. The town posts agendas and minutes on chestertown.com ↗.
One full-time town employee for every 185 residents
On the payroll in March 2025, from the Census Bureau’s Annual Survey of Public Employment & Payroll. Residents: the Census population in the 2024 finance file (5,563).
By department full-time, plus part-time, March 2025
The Census reports one month’s payroll (March); yearly figures are that month × 12, an estimate. Part-timers count half in the bar lengths.
Kent County Public Schools
Chestertown’s K–12 school district, shared with Betterton, Galena, Rock Hall, Millington. It’s its own government, with a budget separate from the town’s.
Of the $54,576 per pupil, $37,507 goes to the classroom (teachers, aides, supplies); the rest to buses, buildings, counselors and administration. Building projects and debt payments aren’t in the per-pupil figure.
Maryland districts overall: 47% local, 44% state, 9% federal.
School year 2023–24. Census Bureau school finance survey.
Chestertown’s votes are counted by county
Maryland reports official results by county and precinct, not by town, so there are no official results for Chestertown alone, and we don’t estimate them. These are Kent County’s results.
Donald J TrumpRepublican50.0%5,561 votes
Kamala D HarrisDemocrat47.2%5,251 votesOthers: 2.8% (316 votes).
Most votes in Kent County: Donald J Trump
Maryland: Harris 62.6%, Trump 34.1%
100% of Chestertown lies in Kent County. Every 2024 race in Kent County is on the county’s page.
Kent County’s 2024 results →Official 2024 general election returns, as certified (MIT Election Data + Science Lab). Percentages are of votes for candidates; blank and spoiled ballots aren’t counted. Candidates are listed by votes, and party colors are neutral on purpose.
Portraits: Kamala D Harris: official vice-presidential portrait, Lawrence Jackson, The White House, 2021; Donald J Trump: official portrait, Shealah Craighead, The White House, 2017. All are U.S. government works in the public domain. A race shows photos only when every candidate has an official portrait; otherwise every candidate in it gets initials.
From town hall to Washington
Every level of government that speaks for Chestertown.
- 1Your townTown governmentOfficials: chestertown.com ↗
- 2Maryland House of DelegatesState representatives
- 3Maryland SenateState senator
- 4GovernorStatewide
- 5U.S. HouseYour representative in Congress
- 6U.S. SenateBoth represent all of Maryland
Democrat · Republican · other or independent. Tap a name for their official page.
Reach Chestertown’s government
The official site has phone numbers, hours and forms. Neighbors add the rest to the Handbook.
Questions about Chestertown’s government
How much does Chestertown spend per resident?
About $1,069 per resident on day-to-day services in the year to June 30, 2024, as reported to the Census Bureau. In 2022, the last full count, its $1,031 was more than 62% of 37 Maryland cities of 2,500–9,999 that don’t run their own schools.
What is the property tax rate in Chestertown?
Homeowners report a typical bill of $3,966 a year (Census ACS, 2020–24), about 1.15% of the typical home’s value, vs 0.97% across Maryland. For the official rate per $1,000 of assessed value, see chestertown.com.
Who runs Chestertown’s government?
See chestertown.com for current officials. We name an official only when a public source lists a current term, and none does for Chestertown yet.
How did Chestertown vote in 2024?
Maryland counts votes by county and precinct, not by town, so there are no official results for Chestertown alone. Kent County, where 100% of Chestertown lies, voted Trump 50.0%, Harris 47.2% for president; its page has every race.
How many people work for Chestertown?
30 full-time and 12 part-time employees in March 2025, with a March payroll of $189,126 (about $2.3M a year if every month were the same), as reported to the Census Bureau.
Who represents Chestertown in the state legislature?
State Senate District 36 (Steve Hershey) and House of Delegates District 36 (Jay Jacobs, Jeff Ghrist and Steve Arentz). The House of Delegates district also covers 19 other towns. Listed by Open States; districts from the Census Bureau.
Ask neighbors about Chestertown’s government
Neighbors who’ve been to the meetings can help.
Budget and staff: U.S. Census Bureau, Census of Governments (2022, every government) and Annual Survey of State and Local Government Finances (2023–24, a sample) and the Annual Survey of Public Employment & Payroll; day-to-day spending is current operations, with hospitals, utilities and airports apart. School district: Census school finance survey, 2023–24. Property tax: Census American Community Survey, 2020–24. Elections: official 2024 returns via the MIT Election Data + Science Lab; turnout uses Census citizen voting-age population (CVAP, 2020–24). Officials: Open States, names shown only with a current term (checked October 9, 2026). Districts: Census Bureau (119th Congress, 2024 state districts); legislators: Open States and congress-legislators. How Town Hall works →