AARP’s Great Places to Live: Winterset, Iowa

This city has movie-set looks with close proximity to a large city

Veronica Lorson Fowler,

AARP

Published November 19, 2025

AARP’s Great Places to Live is a list of 10 communities that have many of the qualities older people value: good health care, social opportunities, a nice climate, easy to get around, a thriving job market and rank highly on AARP's Livability Index (learn more about the Livability Index here, including how your community ranks). One city that made the list: Winterset, Iowa. To see more Great Places to Live, click here.

Population: 5,366
AARP Livability Index score: 68
Average monthly housing cost: $1,100
Perfect-weather days*: 119 per year

If little Winterset, Iowa, looks like the setting of a movie, that’s because it is. Its historic town square and iconic covered bridges inspired the best-selling novel The Bridges of Madison County, later made into a sweetly romantic film starring Clint Eastwood and Meryl Streep.

About 30 miles southwest of Des Moines, Winterset may have only 5,300 residents, but it boasts the recently restored Iowa Theater that shows current and vintage movies; the Iowa Quilt Museum; and numerous specialty and antiques shops. It has several restaurants, including an old-fashioned drugstore lunch counter, the elegant Petite Cafe for light bites and the upscale Urban on the Square.

“People who visit here often say that they love its authenticity. It’s a classic Midwestern county-seat town,” says Marianne Fons, 76, a quilter, writer and community booster who lives in a stylish converted storefront just off the square. Fons points out that while the proximity to Des Moines helps Winterset thrive, it also has an independent sensibility. “We’re not a bedroom community,” she says. “We’re a living room community.”

Linda Kaysen, 77, is a good example of someone who thrives here. She moved to Winterset from Colorado six years ago to be closer to family and is now on the Friends of the Winterset Library board and a local parks and recreation board, is an officer in her church’s altar and rosary society, and belongs to a quilt guild and two book clubs. “I never imagined I would be as involved in as many organizations and meet as many people as quickly as I did,” she says.

Kaysen also loves being four blocks from her grocery store and one block from her church. Best of all, she can walk to that historic town square and run errands at the post office, the library and the pharmacy. “It’s pretty remarkable that you can manage to do that in this day and age.”

Affordability

The cost of housing in Winterset is 26 percent below the national average. Housing costs — such as taxes, rent, mortgage fees and utilities — average $1,108 per month. Affordable housing can be found not only in rental apartments but also single-family home purchases.

Health care

The Madison County Health Care System includes the Madison County Memorial Hospital and the Health Trust Physicians Clinic, and it operates under the umbrella of MercyOne, a large medical center network based in Des Moines. Other large medical centers are located in Des Moines, about a 45-minute drive.

Culture

The pretty rolling countryside and wooded areas in and around Winterset offer ample opportunities for walking, cycling and hiking, including visits to its six famous covered bridges, built in the late 19th century. Visitors, who come from around the world, can wander around and through each bridge, take in river views and snap photos.

In town, the Winterset Stage offers local productions, the Iowa Quilt Museum has national draw, the beautifully restored art-deco Iowa Theater hosts vintage movies weekly, and a winery and cidery offer tastings and other events.

The town also has a Saturday morning farmers market, or visit the small hobby farms that surround Winterset. They sell vegetables, fruits and flowers; one features alpacas, offering woolen goods for sale, plus alpaca hikes and alpaca yoga.

Winterset stages numerous festivals each year, including the Covered Bridge Festival and the Madison County Fall Crawl, a family-friendly small rural businesses event featuring coffee, cider, wine, beer and a bite to eat.

In August, take a 45-minute drive to the Iowa State Fair and see its famous butter sculptures. The Des Moines Civic Center is a great place to take in a road production of a Broadway musical or attend a classical music concert. Music lovers also enjoy the Des Moines Metro Opera. The Des Moines Art Center has a small but excellent collection.

Getting around

The central community, around the town square, is walkable, but some newer parts of town don’t have sidewalks. The community lacks a city bus system and traditional taxi service, and ride-hailing services tend to be expensive compared to larger cities. But Winterset does have a low-cost door-to-door public transit service for people with disabilities and anyone 60 and older. Rides in town are $3. And driving is easy, as traffic congestion is nearly nonexistent in this small town.

Winterset also has excellent hiking opportunities, with 20 miles of groomed trails throughout the town and county, ideal in warm-weather seasons.

Climate

Spring and autumn are beautiful in Iowa, and summers are relatively comfortable, with July average high temperatures of 85. Winters can be difficult, with several inches of snow per month and brief spells of extreme cold.

Job market

Unemployment in Madison County is just 3.6 percent, creating healthy job opportunities. Leading industries are construction, finance, insurance, real estate, health care, social services and the wholesale and retail trade.

Going out guide

Sunny-day location: Winterset City Park. This 76-acre park is on the National Register of Historic Places. It includes a picturesque stone tower, limestone shelter houses that are perfect for a picnic, a hedge maze and, of course, a covered bridge.

Weekday evening hangout: Iowa Theater. Catch a Throwback Thursday vintage film at this impressively restored movie house on the town square.

Where to take visitors first: The bridges of Madison County! Visit one or all six of the iconic local covered bridges, scattered in and around Winterset.

AARP initiatives

From fraud-watch resources to food insecurity, learn more about AARP initiatives, volunteer opportunities and news from the AARP Iowa office.

*What's a perfect weather day? High temperature between 60 and 85 degrees, with less than 1 millimeter of rain. Source: Yahoo News analysis of federal data.

Veronica Lorson Fowler is a freelance writer and former newspaper reporter and magazine editor living in Ames, Iowa. She has also written for the Des Moines Register and Better Homes and Gardens’ special interest publications.