Chestertown leans Republican by roughly 16 points: about 42% of voters vote Democratic and 58% Republican.
About 73% of adults in Chestertown typically vote, above the U.S. average of about 62%. Among adults in Chestertown, ~31% vote Democratic, ~42% Republican, and ~27% don't vote. The map below shows estimated turnout by block group.
How Chestertown compares
Among cities within 25 miles, Chestertown leans more Republican than 24 of 56 neighbors.
Chestertown runs about 28 points more Republican than New York as a whole. New York leans Democratic overall, while Chestertown is one of the few Republican-leaning pockets.
Politics vary noticeably by neighborhood within Chestertown. The northeast side is the most Republican-leaning (R+26) and the east side is the least Republican-leaning (R+11), a spread of about 15 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.
Chestertown votes against the grain of New York. New York leans Democratic overall, while Chestertown runs about 28 points more Republican. A high family-household share predicts Republican voting, and about 75% of households in Chestertown are family households, above 75% of cities.
Cancer-screening access and voter turnout
Places with high colon-cancer-screening access tend to turn out at a higher rate; Chestertown, NY sits in the top tenth nationally on this measure. Cancer screening does not drive turnout; it reflects income, insurance, and healthcare access.
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 66%, about 6 points above the U.S. average of 60%. Learn more about the findings and methodology on the political spectrum map.
Nearby Cities
- South Horicon, NY R+18
- Darrowsville, NY R+25
- Wevertown, NY R+4
- Riparius, NY R+18
- Brant Lake, NY R+18
- Pottersville, NY R+25
- Adirondack, NY R+19
- Igerna, NY R+27
- Thurman, NY R+26
- Johnsburg, NY R+15
Cities with Similar Populations
- Descanso, CA R+34
- Helen, MD R+17
- Blanch, NC R+10
- Argenta, IL R+45
- Harding Lakes, NJ R+7
- Oakland, NE R+46
- Oquawka, IL R+37
- Sunray, OK R+71
- Hickory Tavern, SC R+73
- Harvey, ND R+51
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Sources and methodology
Precinct-level voting records used to fit the model come from New York 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.