Missouri's Best Place For The Upper Middle Class To Retire Is A Vibrant City Full Of Fun Activities

Missouri has something for everyone with a mix of major metropolitan hubs like Kansas City and St. Louis, cute college towns like Columbia, and scenic natural beauty in places like the Ozarks. That variety means that retirees have plenty of options to find the ideal place that works for them for their sunset years. For those in the upper middle class, one of the best places to retire in Missouri is the city of Chesterfield. It's a suburb near the Missouri River about 30 minutes west of downtown St. Louis, and it was the only Missouri city to make GOBankingRates' top 50 "best retirement towns for the upper middle class." With its wealth of activities, it's clear why the thriving community of Chesterfield is a good retirement choice.

GOBankingRates used Pew Research Center data to define the upper middle class as those who earned between $120,896 and $155,438 per year. Chesterfield makes for a good retirement destination for that income bracket because, according to Payscale, housing costs are higher in Chesterfield compared to the national average, and Zillow puts the median home price at close to $600,000. However, you will find that utilities and groceries are cheaper than elsewhere in the country.

Chesterfield is a newer city, having been established in 1988. This thriving community is continuing to grow, continuing to give its citizens a high quality of life. That commitment to thoughtful growth can be seen at the site of the former Chesterfield Mall. Torn down between 2024 and 2025, $2 billion is being invested into creating a new mix of walkable commercial, green, and residential space, including some senior-specific housing.

Over 49,000 people call this city home, with more than 25% of the population over the age of 65. The Chesterfield Parks and Recreations Department hosts a number of activities specifically for older adults to enjoy, like trivia night, bingo, pickleball, and mahjong lessons. For active retirees, the city has a number of parks and green spaces. The 12-mile-long Monarch Levee Trail in Chesterfield is open for hiking and biking, and it connects to the scenic Katy Trail, America's longest developed rail-trail. For an even wilder green space, Castlewood State Park, a one-stop destination for biking, hiking, and fishing, is only a 20-minute drive from Chesterfield.

Around the city, you can find public art, like the sculptures in Chesterfield's Central Park, which also has trails, picnic tables, a playground, and places to fish. River's Edge Park is a good spot for birdwatching with a 1.6-mile trail around the lake and through the forest. You can also fish there from the dock or out on a non-motorized boat. It's a popular and pretty spot. As one Yelp reviewer noted: "The lake has plenty of benches around the perimeter for viewing the scenery or taking a break. There is even a path to the river which makes for good photos."

Golfers have a number of options for hitting the links in Chesterfield, too. The Landings at Spirit Golf Club is an 18-hole championship course that's open to the public, and has season passes available. There are also a few private clubs in town.

Faust Park in Chesterfield, Missouri, is home to the historic Thornhill Estate, which dates back to the early 1800s and is the oldest governor's house in the state. It's not currently the home for the governor — that's in Jefferson City, Missouri, with its river views and downtown charm — but it's been renovated and restored to look much like it did when it was first built. You can see inside during the occasional free open houses during the year.

Other historic structures at the park include a brick cottage from the 1880s, wood barns, a granary, and smokehouse as well as a working vintage carousel. Plus, there's the Sophia M. Sachs Butterfly House. The 8,000-square-foot conservancy has hundreds of butterflies from dozens of different species; they might even land on you. It's quite the experience. "It felt magical," one person wrote on Tripadvisor. "Hundreds of butterflies flying overhead. The plants were all so vibrant.... my grandson is still talking about it."

Each season brings something new and exciting to Chesterfield. In spring, there's an annual golf tournament and an Easter Egg hunt in Central Park. The Sounds of Summer is a free music festival with performances at the Chesterfield Amphitheater. There are also free concerts at Faust Park every Tuesday from June through mid-August. Chesterfield in general is a fall foliage showstopper, and the annual Chesterfield Fall Festival features food, rides, a pumpkin patch, and hayrides. There's also the Folklife Festival in September, which takes you back in time with cooking demonstrations, pottery making, and arts and crafts from the 1800s. Then, to celebrate the holidays, there are events like the Senior Holiday Carnival at City Hall and Cookies at the Carousel, where little ones can meet Santa.