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Chestertown

A town of 5,594 people in Maryland
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Now in Chestertown

What’s happening this week

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Weather

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Around town

Local news

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Headlines via Google News · Articles belong to their publishers.

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Around town

The places and views that make it Chestertown

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Outdoors in Chestertown

Parks & trails →
Map of Chestertown: conserved land, trails and the top places to walk
Conserved land0.5%10 of 1,889 acres
Trails0.9 mi0.3 mi per sq mi
Parks & preserves42 conserved acres per 1,000 residents

Trails & parks © OpenStreetMap contributors · Conserved land: USGS PAD-US

Kent County Courthouse, Jail, Cross Street1933
From Chestertown’s story

Kent County Courthouse, Jail, Cross Street, 1933

Photo · Wikimedia Commons

Landmark of the day

All 15 historic places →
Brampton

Brampton

Building · on the Register since 1983

Brampton is a historic home located near Chestertown, Kent County, Maryland. It is a transitional Greek Revival / Italianate-influenced dwelling built about 1860.

15 on the National Register · 1 National Historic Landmark · #9 in MDHistoric places →
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Know Chestertown

The town at a glance, and the guide to how things work

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About Chestertown

Town in Maryland, United States
1706Established
5,532Population
2.9 sq miArea
20 ftElevation

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.

Official town website ↗

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

Living in Chestertown

Housing in Chestertown

$391K▲ 1.9% in a year Typical home value · Zillow

The typical Chestertown home is worth about $391,000, up 1.9% in a year, 9% below the Maryland typical home.

Zillow Home Value Index · Redfin Data CenterHousing market →

Safety in Chestertown

C

Safety Grade C

Chestertown reports more crime per resident than most U.S. towns we grade: about 71% report less. Within Maryland, it does better than 52% of towns.

Violent crime per 1,000
Chestertown 3.3
Maryland 3.7
U.S. 3.3
Property crime per 1,000
Chestertown 13.4
Maryland 18.5
U.S. 15.5
FBI crime data, 2025 · crimes reported to policeCrime & safety →

Work & commute in Chestertown

Full picture →

About one in 3 of Chestertown’s working residents works in town. The top destinations are Baltimore (5%), Centreville (3%) and Rock Hall (2%). Half commute less than 12 miles.

Baltimore
5%
Centreville
3%
Rock Hall
2%
Dover, DE
1%
Census LEHD 2023 · ACSWork & commute in Chestertown →

Health in Chestertown

B

Health Grade B

Healthier than 62% of U.S. towns on seven CDC estimates, and 92% of towns with similar incomes.

Compared with Maryland

2better than MD·8worse

of 32 measures CDC estimates. The other 22 are too close to call.

BetterToo close to callWorse

What stands out

Care nearby

University of Md Shore Medical Ctr at ChestertownChestertown · 0.5 mi · ER
Chestertown Health CenterChestertown · 0.6 mi · sliding-scale fees
Primary careShortage · county-wide
DentalNo shortage
Mental healthShortage · county-wide
CDC PLACES 2025 · modeled estimates for adults · CDC's estimate for Chestertown · CMS · HRSAHealth in Chestertown →

Natural hazards in Chestertown

19
Very low

Expected storm and flood damage is higher than in 19% of U.S. communities.

🌀 Hurricanes🌊 Inland flooding🌡️ Heat waves
FEMA National Risk Index December 2025 · OpenFEMANatural hazards in Chestertown →

Climate in Chestertown

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Chestertown has chilly winters and warm summers. A typical July afternoon reaches 88°, a January night drops to 27°, and about 17 inches of snow falls in a normal winter.

45° / 28°Winter
64° / 45°Spring
85° / 67°Summer
68° / 49°Fall
NOAA U.S. Climate Normals, 1991–2020Climate in Chestertown →

Schools in Chestertown

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C

School Grade C

The public schools Chestertown’s kids attend, from kindergarten through graduation, trail 72% of Maryland’s districts on state tests and graduation. Among towns with similar incomes, they rank near the bottom.

See how Chestertown’s schools compare in MD →
DistrictKent County Public SchoolsSchools4

School data from the U.S. Department of Education (NCES, EDFacts). The School Grade is our own summary of state test results and graduation rates, graded within MD. Ratings are from neighbors.

Chestertown is a college town

Colleges →
22%

of Chestertown’s residents are enrolled in college. Washington College has about 916 students on campus.

College Scorecard · IPEDSColleges in Chestertown →

Chestertown’s library

Library details →
Chestertown Branch408 High St. · part of Kent County Public Library
Fine-freeE-books40 hrs a week
IMLS Public Libraries Survey · FY2024Chestertown Branch →
Famous people from ChestertownWriters, athletes, leaders and more who were born in Chestertown.Meet them →

How things work in Chestertown

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The porch light’s on

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Boundary source: https://tigerweb.geo.census.gov/arcgis/rest/services/TIGERweb/Places_CouSub_ConCity_SubMCD/MapServer/18 · 2025-01-01