Chestertown leans slightly Democratic by roughly 8 points: about 54% of voters vote Democratic and 46% Republican.
About 71% of adults in Chestertown typically vote, above the U.S. average of about 62%. Among adults in Chestertown, ~38% vote Democratic, ~33% Republican, and ~29% don't vote. The map below shows estimated turnout by block group.
How Chestertown compares
Among cities within 25 miles, Chestertown leans more Democratic than 95 of 107 neighbors.
Chestertown runs about 20 points more Republican than Maryland as a whole.
Politics vary noticeably by neighborhood within Chestertown. The south side runs the most Democratic (D+33) and the southeast side runs the most Republican (R+26), a spread of about 58 points.
Why Chestertown leans the way it does
This analysis examined 14,881 data points per city to find what predicts political lean and turnout. The items below are a few correlations that stood out for Chestertown, not a ranked or complete list of what matters most.
Areas with high college attainment vote Democratic. About 44% of adults in Chestertown hold a bachelor's degree, about 15 points above the U.S. average of 28%. Dense areas vote Democratic, and Chestertown sits in the top fifth on density (about 36%, above 83% of cities). A high never-married share predicts Democratic voting, and about 36% of adults in Chestertown have never been married, above 89% of cities.
Population density and Democratic lean
Places with high population density tend to lean Democratic; Chestertown, MD sits in the top quarter nationally on this measure.
Why turnout in Chestertown looks the way it does
Areas with strong routine healthcare access turn out at higher rates. Chestertown is in the top quarter nationally for routine-care measures such as insurance coverage, preventive screenings, and dental visits. The dental-visit rate here is about 62%. Learn more about the findings and methodology on the political spectrum map.
Nearby Cities
- Foxley Manor, MD D+17
- Kingstown, MD D+6
- Pomona, MD D+6
- Ewingville, MD R+36
- Fairlee, MD R+5
- Worton, MD R+15
- Rolphs, MD R+31
- Georgetown, MD R+27
- Johnsontown, MD R+40
- Crumpton, MD R+34
Cities with Similar Populations
- Pecos, TX R+27
- Clarendon Hills, IL D+14
- Sykesville, MD R+10
- South Apopka, FL D+36
- Box Elder, SD R+59
- Cedar Hills, UT R+43
- Social Circle, GA R+40
- Leesville, SC R+61
- Barnesville, GA R+20
- Belle Vernon, PA R+30
Sources and methodology
Precinct-level voting records used to fit the model come from Maryland State Board of Elections, distributed by the Voting and Election Science Team. Demographic inputs come from the U.S. Census Bureau (ACS 5-year estimates and the 2020 Decennial Census). Health and environmental inputs come from the CDC (PLACES and the Environmental Justice Index). Land cover comes from the USGS and EPA. Election-day and lead-up weather come from PRISM 4km daily grids and the NOAA Global Historical Climatology Network. Mail-voting and election-administration patterns come from the MIT Election Lab's Survey of the Performance of American Elections. Block-group crime detail comes from CrimeGrade. Internet data and modeling support provided by ISPreports.org.
Modeling and analysis by the BestNeighborhood data science team. Full methodology and findings: political spectrum map.
Methodology reviewed by the BestNeighborhood data team. Last updated May 2026.