Each edition grades its towns against each other only.
A town of 3,795, settled in 1860. 2.6 times the nonprofits per person than the typical Mississippi town.
Winona earns a D, 71st of 99 graded towns in Mississippi, mostly because of health and incomes. On CDC health estimates it is near the bottom nationally. The median household income is $32K, and 32% of residents live below the poverty line. One bright spot: it is more walkable than 80% of U.S. towns. 32% of residents live below the poverty line in Winona, against 21% in Mississippi’s towns and 9.6% across U.S. towns. No town in Mississippi scores higher than Winona on civic life. Winona has 7 places on the National Register of Historic Places, among them James C. Purnell House and Stafford's Wells Hotel.
Where Winona beats most towns, and one thing worth knowing.
| Widest gap | Winona | MS |
|---|---|---|
| More older adults who have lost all their teeth | 33.4% | 18.5% |
Census counts: 1,204 in 1880, a peak of 6,177 in 1980, 4,505 in 2020. The archive holds 16 old photos and papers going back to 1909 and a map from 1966 on.
7 places on the National Register of Historic Places.
Each subject compared with towns across the country (schools within Mississippi), ordered by how far Winona is from typical.
How TownRatings grades towns →
Who provides power, water and the rest in Winona, and how to reach them.
EPA SDWIS (Oct 9, 2026) · HIFLD + EIA-861 2025 · Census 2020 ZCTAs · NCES 2024–25 · registration: vote.gov, updated Nov 18, 2024.
Ordered by what stands out in Winona.
Winona trades workers with Grenada and other neighbors, has home values still below their peak and has hotter summers than most of the country, though not than most of Mississippi.
38% of Winona adults say their health is fair or poor. Among 101 Mississippi towns, just 9 have a higher share of adults who report frequent mental distress than Winona. 25% of Winona adults smoke cigarettes.
| Winona | Mississippi towns | U.S. towns | |
|---|---|---|---|
| Fair or poor health (CDC PLACES) | 38% | 27% | 19% |
| Smoke cigarettes (CDC PLACES) | 25% | 18% | 14% |
| Diabetes (CDC PLACES) | 24% | 16% | 12% |
| Get no exercise (CDC PLACES) | 47% | 36% | 25% |
| What stands out | Winona | MS |
|---|---|---|
| Fewer binge drinkers | 10.5% | 13.6% |
| More adults treating high blood pressure | 83.6% | 79.7% |
| More older adults who have lost all their teeth | 33.4% | 18.5% |
CDC PLACES 2025 · modeled estimates for adults · CMS · HRSA
Its public schools are run by the Winona-Montgomery Consolidated School District. Two of its 4 schools are below, each with why it’s listed. The largest public high school is Winona Secondary School, with 502 students.
| School | Level | Students | Letter |
|---|---|---|---|
| Winona Elementary SchoolLargest public elementary schoolGrades PK–6 | Grades PK–6 | 567 | C+ |
| Winona Secondary SchoolLargest public high schoolGrades 7–12 | Grades 7–12 | 502 | C+ |
NCES · EDFacts · graded within MS on state tests and graduation
The typical value, about $131K, is 14% below its September 2022 peak. At about $131K, home values are down 6% in five years, against a rise of 11% across Mississippi.
The typical Winona home is worth about $131,000, up 4.5% in a year, 33% below the Mississippi typical home.
Zillow Home Value Index · Redfin Data Center
July afternoons average 90.7°: hotter than most of the country, but cooler than 79% of Mississippi places with climate records; January nights average 33.4°.
Winona has mild winters and warm summers, with plenty of rain. Winona’s January low is 33°F. Snow is almost unheard of.
| Winona | Mississippi towns | U.S. towns | |
|---|---|---|---|
| January low | 33°F | 36°F | 22°F |
| July high | 91°F | 91°F | 85°F |
NOAA U.S. Climate Normals, 1991–2020
Winona has about as many jobs (1,637) as working residents, but only 420 people both live and work here. Jobs based here fell from 2,241 in 2013 to 1,637.
The average trip to work in Winona is 18 minutes. Since 2013, Winona has lost 604 jobs, to 1,637 in 2023. 24% of working residents work locally in Winona.
| Winona | Mississippi towns | U.S. towns | |
|---|---|---|---|
| Average trip to work | 18 minutes | 23 minutes | 25 minutes |
| Median household income | $32,000 | $50,000 | $80,000 |
| Working residents who work in town | 24% | 19% | 8% |
Census LEHD 2023 · ACS
The median household earns $31,932, against $56,447 across Mississippi, one input to its D− for jobs and income.
Adults 18 to 34 are 18% of residents (22% statewide). Winona has lost 15% of its people since 2020, down to 3,795 in the Census Bureau’s 2025 estimate. 20% of adults 25 and older have a bachelor’s degree or more, vs 25% across Mississippi.
| Winona | Mississippi towns | U.S. towns | |
|---|---|---|---|
| Bachelor’s degree or more, 25+ | 20% | 25% | 29% |
| Median age | 40.4 years | 37 years | 40.5 years |
55% women, 45% men
About 83 men for every 100 women (the survey’s margin: ±3.4 points). Across Mississippi, 51.5% of residents are women.
| Winona | MS | U.S. | |
|---|---|---|---|
| Under 10 | 9.3% | 12.1% | 11.6% |
| 10 to 17 | 16.4% | 11.2% | 10.3% |
| 18 to 24 | 9.5% | 9.8% | 9.1% |
| 25 to 34 | 8.2% | 12.6% | 13.7% |
| 35 to 44 | 10.8% | 12.6% | 13.2% |
| 45 to 54 | 9.9% | 12% | 12.2% |
| 55 to 64 | 14.8% | 12.6% | 12.7% |
| 65 to 74 | 10.1% | 10.4% | 10.2% |
| 75 and older | 11% | 6.8% | 7% |
| No diploma | 20.4% | 12.9% | 10.4% |
| High school | 32.9% | 29.9% | 26% |
| Some college | 19.7% | 21.2% | 19.1% |
| Associate’s | 7% | 10.9% | 8.8% |
| Bachelor’s | 10.8% | 15.3% | 21.6% |
| Graduate | 9.3% | 9.9% | 14.1% |
Census population estimates, 2025 · U.S. Census Bureau · ACS 2020-2024 5-year estimates · in a town of 3,800, single groups can be off by several points
Expected storm and flood damage is lower than in 51% of U.S. communities.
FEMA National Risk Index · OpenFEMA
None within 15 miles of Winona; the nearest are
About 8 of every 100 Winona residents are enrolled in college, against 6 across Mississippi.
5,043 counted in 2010 and 4,505 in 2020; an estimated 3,795 in 2025.
The decline has continued: down 15.4% since 2020, after 10.7% in the decade before.
U.S. Census 2010 & 2020 counts · Census Bureau estimate, July 1, 2025
7 places in Winona on the National Register of Historic Places.
19 notable people were born in Winona.
City in Mississippi, United States
Winona is a city in and the county seat of Montgomery County, Mississippi, United States. The population was 4,505 at the 2020 census, down from 5,043 in 2010. Winona is known in the local area as "The Crossroads"; the intersection of U.S. Interstate 55 and U.S. Highway 51 and 82 run through here.
From Wikipedia, licensed CC BY-SA 4.0 · facts via Wikidata (CC0)
Short answers, built from the data on this page.
Winona grades D overall, better than 10% of U.S. towns and #71 of 99 in Mississippi. It grades D− for health and B− for schools. Health is its weak spot, with a D−.
That is 2.8 years of the area's median household income ($46,897 across the Grenada, MS area). Cost of living, which also weighs rents, property taxes and how many households pay 30% or more of their income for housing, grades C+.
19 notable people were born here, including Donald H. Peterson and Pops Staples.
