Chestertown grades C− overall, ranked 232nd of 259 in Maryland, with clear strengths and some subjects that lag. It is easier to get around on foot or by transit than 94% of U.S. towns and natural-hazard risk is low. On the other side, homes are expensive, about $387K for a typical one and 4.8 times the county’s $80K median household income. History is its standout character grade: an A+, better than 98% of U.S. towns, with 15 places on the National Register. 35% of working residents work locally in Chestertown, where Maryland’s towns sit at 3.1% and U.S. towns at 8%. Its National Register listings include Chestertown Historic District and BERNICE J. (skipjack). On civic life, just 2 of Maryland’s 98 towns do better.

StrongestA⁺History AWalkability ACivic lifeWeakestDCost of living CSafety

What makes Chestertown stand out

Where Chestertown beats most towns.

Chestertown Historic District

HistoryA⁺

Settled in 1706

A history going back 320 years.

Jobs vs. working residents

Jobs here4,381

Residents who work1,763

Work

2.5 jobs for every working resident

A regional job hub: more jobs per worker than 96% of U.S. towns

Census LEHD 2023.

WalkabilityA

More walkable than 94% of U.S. towns

24.8% of workers walk, bike or ride transit

EPA National Walkability Index; Census ACS.

Chestertown Historic District · National Register of Historic Places

Chestertown’s story

320 years in pictures

Chestertown Historic District is a National Historic Landmark, the National Register’s top tier. Its founding year, 1706, comes before those of 96% of the Maryland towns we grade with a known year.

Census counts: 1,539 in 1860, 5,532 in 2020. The archive holds 18 old photos and papers going back to 1933 and 5 maps from 1901 on.

15 places on the National Register of Historic Places.

1706Chestertown is settled

Explore the history →

How Chestertown grades

Each subject compared with towns across the country (schools within Maryland), ordered by how far Chestertown is from typical.

How grading works

WalkabilityEPA walkability 9.1 of 20; 8.6% of households have no carAOpen →Cost of livingDOpen →Hazard riskFEMA risk higher than 19% of U.S. communities; hurricanes tops the listA⁻Open →SafetyCOpen →Jobs & incomeCOpen →SchoolsC⁺Open →HealthUniversity of MD Shore Medical Center at Chestertown 0.5 miles awayBOpen →

Character Graded, but not part of the overall grade.

Outdoors1 mile of trail; 0% conserved landC⁺Open →History14 notable people born hereA⁺Open →Civic life9.1 community nonprofits per 1,000 residentsAOpen →

Described, not graded Taste, not quality: snow or an older crowd is neither good nor bad.

Climate–Open →Housing market–Open →Who lives hereMedian age 32.6; 53% of adults have a four-year degree–Open →

How TownRatings grades towns →

Getting set up

Moving to Chestertown: who provides what

Who provides power, water and the rest in Chestertown, and how to reach them.

The full setup list →

PowerDelmarva Power21.8¢/kWh · EIA 2025HIFLD · EIA

WaterTown of Chestertown water system1 health-based violation in 5 years · EPAEPA

Internet7 providers100% of addresses get 100/20 MbpsFCC

Trash & dumpNot on file yetWe don’t have Chestertown’s trash rules yet

SchoolsKent County Public SchoolsWhich school depends on your addressNCES

Register to voteOnlineIn Maryland you can register online until 21 days before Election Day, in person up to and including Election Day, or by mail (postmarked 21 days before).vote.gov

Who runs elections hereKent County Board of ElectionsKent County; contacts on the Handbook page.FVAP, Mar 2018

ZIP code2162021620 100%Census 2020

EPA SDWIS (Oct 9, 2026) · HIFLD + EIA-861 2025 · Census 2020 ZCTAs · NCES 2024–25 · registration: vote.gov, updated Mar 11, 2026.

The data

Ordered by what stands out in Chestertown.

Chestertown is shaped by its college students, draws workers from Kingstown and beyond and is healthier than towns with similar incomes.

Work & commuteJobs & income grade C

Compared with most of Maryland and the rest of the country, the median household income in Chestertown is lower

4,381 jobs are based in Chestertown, 2.5 for every working resident, so most of the people who work here commute in. The average commute takes 19.9 minutes, against 31.1 across Maryland.

Chestertown’s median household income is $54,000. Since 2013, Chestertown has added 409 jobs, to 4,381 in 2023. 12% of residents live below the poverty line in Chestertown.

35%work in town

	Chestertown	Maryland towns	U.S. towns
Average trip to work	20 minutes	32 minutes	25 minutes
Median household income	$54,000	$113,000	$80,000
Below the poverty line	12%	7%	9.6%
Work from home	14%	18%	11%

Where working residents work

In Chestertown35%

Baltimore5%

Centreville3%

Rock Hall2%

Dover1%

12 mi

median commute distance

4,381

jobs based in Chestertown

A job hub

jobs vs. working residents

Walkability grade: more walkable than 94% of U.S. towns

Full pageChestertown’s work & commute pageOpen the page

The jobs here4,381 jobs based here · A job hub Where people work35% work in Chestertown Commute times20 minutes · The average commute How far they goHalf commute less than 12 miles

Census LEHD 2023 · ACS

SchoolsC⁺

Public schools in Chestertown fall behind 64% of Maryland districts

Its public schools are run by the Kent County Public Schools. Two of its 4 schools are below, each with why it’s listed.

36%of MD districts it outscoresC⁺School Grade

School	Level	Students	Letter
Kent County Middle SchoolLargest public middle schoolGrades 6–8	Grades 6–8	354	C⁺
Chestertown Christian Academy PrivateLargest high schoolGrades PK–12	Grades PK–12	217	–

Full pageChestertown’s schools pageOpen the page

The districtsKent County Public Schools Every school4 schools · Kent County Middle School Questions“Are Chestertown’s schools good?”

NCES · EDFacts · graded within MD on state tests and graduation

Who lives here

Fewer middle-aged adults than Maryland overall

21.8% of residents are enrolled in college, against 6.9% statewide, which pulls the median age down. The median household earns $54,346, against $103,678 across Maryland, one input to its C for jobs and income.

Adults 35 to 64 are 22% of residents (40% statewide); adults 18 to 34 are 36% of residents (22% statewide). 26% of Chestertown residents are 65 or older. Chestertown has grown 2.2% since 2020, to 5,658 residents in the Census Bureau’s 2025 estimate.

32.6median age · MD 39.4

	Chestertown	Maryland towns	U.S. towns
Aged 65 or older	26%	16%	18%
Under 18	16%	23%	22%
Median age	32.6 years	39.4 years	40.5 years
Bachelor’s degree or more, 25+	53%	42%	29%

ChestertownMarylandUnited States

MDU.S.

Ages · share of residents

27%

Education · adults 25 and older

No diploma9%

High school19%

Some college13%

Associate’s6%

Bachelor’s29%

Graduate25%

Women and men · all residents

56% women, 44% men

About 78 men for every 100 women (the survey’s margin: ±3.5 points). Across Maryland, 51.3% of residents are women.

Ages and education in Chestertown
	Chestertown	MD	U.S.
Under 10	9.2%	11.9%	11.6%
10 to 17	6.6%	10.3%	10.3%
18 to 24	27.1%	8.5%	9.1%
25 to 34	8.7%	13.2%	13.7%
35 to 44	8.1%	13.6%	13.2%
45 to 54	7.2%	12.6%	12.2%
55 to 64	6.9%	13.3%	12.7%
65 to 74	10.3%	9.9%	10.2%
75 and older	15.8%	6.8%	7%
No diploma	8.6%	8.9%	10.4%
High school	19.3%	23.4%	26%
Some college	12.9%	17.4%	19.1%
Associate’s	5.9%	6.8%	8.8%
Bachelor’s	28.7%	22.7%	21.6%
Graduate	24.5%	20.8%	14.1%

Full pageChestertown by the numbersOpen the page

Ages32.6 median age · 26% are 65 or older Schooling53% have a four-year degree Homes52% own their home · Homeowners Income$54K a year · Median household income

Census population estimates, 2025 · U.S. Census Bureau · ACS 2020-2024 5-year estimates

Natural hazardsHazard risk grade A⁻

Very low risk in Chestertown, with hurricanes at the top

Expected storm and flood damage is lower than in 81% of U.S. communities. Since 1979, 34 flood insurance claims have been paid out in Chestertown.

19risk score of 100

FEMA risk score

HurricanesInland floodingHeat waves

paid flood claims since 1979

federal disasters paid out here

Full pageChestertown’s hazards pageOpen the page

What it facesVery low risk Flood claims34 paid flood claims · Since 1979 Past disasters8 federal disasters · Paid out in Chestertown Get ready0.1 events a year, on average · Ready for hurricanes

FEMA flood insurance claims · FEMA National Risk Index · OpenFEMA

SafetyC

More crime per resident in Chestertown than in 72% of U.S. towns

The violent crime rate in Chestertown is 3.3 per 1,000 residents. Within Maryland, it does better than 51% of towns.

28%of U.S. towns report more crimeCSafety Grade

	Chestertown	Maryland towns	U.S. towns
Violent crimes per 1,000 (2025)	3.3 per 1,000 residents	2.3	1.6
Property crimes per 1,000 (2025)	13.4 per 1,000 residents	14.4	9.9

Violent crime per 1,000 residents

Chestertown3.3

Maryland3.7

U.S.3.3

Property crime per 1,000 residents

Chestertown13.4

Maryland18.5

U.S.15.5

28th

percentile among U.S. towns we grade

51st

percentile among MD towns

violent crimes reported in 2025

property crimes reported in 2025

Full pageChestertown’s safety reportOpen the page

Violent crime by type3.3 violent crimes per 1,000 Crime over the yearsSteady since 2023 Questions“Is Chestertown, MD safe?”

FBI crime data, 2025 · crimes reported to police

Climate

Chestertown has four seasons and pleasant summers

Chestertown has chilly winters and warm summers. July afternoons reach 88°, January nights drop to 27° and about 17 inches of snow falls in a winter.

17″snow a winter

Typical low → high °F

Winter28–45°

Spring45–64°

Summer67–85°

Fall49–68°

Nov 5

typical first frost

Apr 3

typical last frost

+1.5°

vs. the 20th-century average

Full pageChestertown’s climate pageOpen the page

A year of weatherJuly highs 88°, January lows 27°Rain & snow17″ of snow a winter · 44 inches of rain and snow a year Heating & coolingMostly a heating bill Then and now+1.5° vs. the 20th century · Warmer than the 20th-century average

NOAA U.S. Climate Normals, 1991–2020

HealthB

Chestertown ranks healthier than 62% of the country’s towns

Against the 7,224 U.S. towns with household incomes like Chestertown’s, it is healthier than 91%, so its B isn’t only a matter of income. Within Maryland it is less healthy than 67% of the 261 graded towns: Maryland sets a high bar.

Chestertown beats the Maryland average on 2 of 32 CDC measures and trails it on 8.

62%healthier than U.S. townsBHealth Grade

	Chestertown	Maryland towns	U.S. towns
High blood pressure (CDC PLACES)	40%	35%	35%
Diabetes (CDC PLACES)	13%	12%	12%
Depression (CDC PLACES)	23%	20%	23%
Binge drink (CDC PLACES)	15%	14%	16%

32 measures vs. Maryland

2 better22 too close to call8 worse

What stands out	Chestertown	MD
More adults screened for colon cancer	72.7%	68.2%
More adults treating high blood pressure	79%	76.6%
More adults with heart disease	7.8%	5.8%

University of MD Shore Medical Center at Chestertown

0.5 mi away · emergency room

2 of 3

care shortages: primary care, mental health

33rd

percentile among MD towns

Full pageChestertown’s health reportOpen the page

Everyday habitsFewer adults sleeping under 7 hours Hospitals & doctors nearby0.5 miles to an ER · University of MD Shore Medical Center at Chestertown How adults are doingMore adults in frequent mental distress Every CDC estimateBetter than MD on 2 of 32

CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA

HousingCost of living grade D

Chestertown’s grade for cost of living is a D

68.3% of renter households pay 30% or more of their income for housing, against 51.5% across Maryland.

The typical Chestertown home is worth about $387,000, up 1.9% in a year, 9% below the Maryland typical home.

$387KZillow home value

	Chestertown	Maryland towns	U.S. towns
Households that own their home	52%	74%	73%
Median rent	$1,206 a month	$1,810 a month	$1,185 a month

Typical home value

Chestertown$387K

Maryland$425K

+1.9%

value change, 1 year

Full pageChestertown’s housing & cost-of-living pageOpen the page

Prices over the yearsUp 1.9% in a year Years of income to buyA typical home costs 7.1 years of income Rents$1,206 a month · Median rent

Zillow Home Value Index · Redfin Data Center

OutdoorsC⁺

A smaller share of Chestertown is conserved land than in the typical Maryland or U.S. town

0.5% of the land in Chestertown is conserved. 0.9 miles of trail in 4 parks and preserves. The biggest park or preserve is Rolling Road Park, at 20 acres.

0.5%conserved

	Chestertown	Maryland towns	U.S. towns
Conserved land	0.5%	9.5%	4.3%
Miles of trail per square mile	0.3 miles per square mile	0.6	0.4

0.5%

conserved · 10 of 1,889 acres

0.9 mi

of trails · 0.3 per sq mi

Biggest places to walk	Trails	Acres
1. Rolling Road Park	0.1 mi	20
2. Wilmer Park	—	6
3. Village At Chestertown Park	—	2

Full pageChestertown’s outdoors pageOpen the page

Trail map0.9 miles of trail, mapped Pick a walk0.1 miles of trail · Rolling Road Park Conserved land0.5% conserved · 10 acres protected Questions“Where can I hike in Chestertown?”

Nearby attractions

M&T Bank Stadium and 66 more within 40 miles

Museums, parks, gardens and other places to visit around Chestertown. Close and well known come first.

All 300 attractions →

Big draw30 mi Stadium & arenaM&T Bank Stadium

30 mi Stadium & arenaOriole Park at Camden Yards

26 mi MuseumNS Savannah

27 mi National MonumentFort McHenry National Monument and Historic Shrine283K visitors a year

30 mi MuseumWalters Art Museum

30 mi Stadium & arenaCFG Bank Arena

Sources: National Park Service · ski areas © OpenSkiMap / OpenStreetMap contributors · Wikidata · Wikipedia readership · photos via Wikimedia Commons

Photo credits

M&T Bank Stadium: United States Department of Defense Cherie Cullen, Public domain · Oriole Park at Camden Yards: Keith Allison, CC BY-SA 2.0 · NS Savannah: Elton Lord/Atomic Energy Commission, Public domain · Fort McHenry National Monument and Historic Shrine: ScottyBoy900Q at English Wikipedia, CC BY-SA 3.0 · Walters Art Museum: Dylan k, CC BY-SA 3.0 · CFG Bank Arena: Don Woods, CC BY-SA 3.0

Keep exploring

Everything we know about Chestertown

20pages on Chestertown

The big questions

SchoolsC⁺Behind 64% of MD districts · 4 schools SafetyC3.3 violent crimes per 1,000 residents (2025)HealthBBetter than MD on 2 of 32 CDC measures Cost of livingD$387K typical home · up 1.9% in a year Work & commuteC$54K median household income · 4,381 jobs here Natural hazardsA⁻FEMA risk higher than 19% of U.S. communities · hurricanes

Out and about

OutdoorsC⁺1 mi of trails · 0% conserved land PlacesAttractions300 nearby · Charles Sumner Post No. 25, Grand Army of the Republic under 1 mi LibraryAChestertown Branch CollegesWashington College, in town

The story

HistoryA⁺Settled 1706 · 15 on the National Register Famous people14 born in Chestertown Town Hall & politicsOne full-time town employee per 189 residents Climate88° summer highs · 17″ of snow

Day to day

News3 recent stories about Chestertown WeatherHandbookZIP code 21620, 21690 Town SquareNeighbors

After high school

Colleges nearby

1 within 15 miles of the center of Chestertown

Washington CollegeUniversity or college · Private nonprofit · ChestertownIn town$55,326 tuition

College town 22 of every 100 Chestertown residents are enrolled in college, against 7 across Maryland.

Prices by family income, graduation and earnings →

A job hub

Every workday, about 3,767 people come to Chestertown for work

Where Chestertown’s working residents go each day. Line width shows the share.

4,381jobs based in Chestertown

35%of working residents work in town

12 mimedian commute distance

Census LEHD 2023

Landmarks

15 places in Chestertown on the National Register of Historic Places.

All landmarks →

Chestertown Historic DistrictNational Historic Landmark

Denton House

Widehall

Rose Hill

Famous people from Chestertown

14 notable people were born in Chestertown.

See all 14 →

James PealePainter from the United States · 1749–1831

George VickersAmerican politician · 1801–1879

Philip ReedAmerican politician · 1760–1829

William O. Baker(1915-2005) American chemist · 1915–2005

James LloydAmerican politician · 1756–1830

Ezekiel F. ChambersAmerican politician · 1788–1867

About Chestertown

Town in Maryland, United States

Official town website ↗

Chestertown is a town in Kent County, Maryland, United States. The population was 5,532 as of the 2020 census. It is the county seat of Kent County, the oldest county in Maryland.

From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)

Established: 1706
Area: 2.9 sq mi
Elevation: 20 ft
ZIP code: 21620, 21690

Questions about Chestertown

Short answers, built from the data on this page.

Is Chestertown, MD a good place to live?

Chestertown grades C− overall, better than 21% of U.S. towns and #232 of 259 in Maryland. It grades B for health, C for safety and C+ for schools. Cost of living is its weak spot, with a D.

Is Chestertown, MD safe?

Within Maryland, it does better than 51% of towns.

Is Chestertown, MD expensive?

Yes. Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades D.

What is Chestertown, MD known for?

14 notable people were born here, including James Peale and George Vickers.

Post to Chestertown

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Is Chestertown a good place to live?