Winner is an isolated but close-knit small town
Winner is a small town that rises from the isolated plains in the southern part of South Dakota. No interstate passes through this town; it is connected to the rest of the state by a pair of two-lane country highways that intersect at its east end. Although it is a far cry from the nearest major commercial centers, the main drag along the highway hosts grocery stores and restaurants, along with many long-standing family-owned businesses that help this small community thrive. “We’re about as far away from anything as you can get in this part of South Dakota,” says Realtor Rick Shippy of Shippy Realty and Auction, who was born and raised in town. “All the same, we’ve got just about everything you’d need. There’s the hospital, the school district and the John Deere dealership – those would be the major employers, but a lot of family businesses in carpentry and plumbing do very well here. Not bad for being out in the middle of nowhere.”
Midcentury homes with flat, tree-shaded yards define residential areas
Winner’s wide residential streets are lined with a collection of midcentury homes. Sidewalks pass by flat, grassy front yards, often shaded by tall trees. “Most homes here were built out of farms, largely back in the ‘30s, ‘40s and ‘50s,” Shippy says. “There hasn’t been a ton of new construction, and what has gone up are mostly single-story homes. We have an aging population, lots of whom work into their 70s, so ranch-style houses are getting more popular.” Few homes have sold in Winner in recent years. Two ranch-style homes went for $125,000 and $250,000 in 2025, while one townhouse sold for $210,000 in March of 2024.
Winner High boasts a state champion football squad
Three schools form the Winner School District. Winner Elementary, on the west side of town, earns a C-plus grade from Niche. Winner Middle and Winner High both occupy the same building on East 7th Street. The middle school scores a B-minus, while the high school receives a B. In 2024, the Winner Warriors football team won its 10th overall state championship.
Two highways intersect in Winner
U.S. Highway 183 and South Dakota state Route 44 intersect on the east side of Winner, providing the only two major connections to the rest of the state. Usually, traffic is sparse, but during the summer a popular motorcycle rally brings crowds through the town. “Highway 44 is one of the most sought-after routes to the Sturgis Motorcycle Rally,” Shippy says. “Lots of people start out up north on Interstate 90, but they’ll take Highway 44 back because there’s less traffic.” Winner Regional Hospital is located on the south side of town.
Family businesses define the local economy
Winner Super Foods and the County Fair Food Store are available in town grocery options, although residents will have to travel to shop at big-box retailers. “We’re about two hours from Pierre or the big shopping destinations in Rapid City, so once every 2 or 3 months, people might make a trip to one of those cities to go to Sam’s Club or Walmart,” Shippy says. “But in town, we have hardware stores, grocery stores and pretty much any kind of food you’d want to eat.” Popular options include Winner Chicken Dinner, a locally owned restaurant that serves breaded chicken prepared in unique “broaster” air fryers. Small, family-owned businesses like this prop up Winner’s economy. “There are people who do taxes and a couple of attorneys on Main Street, and all your services can be done locally,” he adds. “I know a guy who moved away to get his plumbing trade, then came back to take over his father’s business and has been doing very well ever since. That’s just the kind of town Winner is.”
Hunting, fishing and golf are popular pastimes in Winner
McDonald Park on the south side of town is home to a public swimming pool, a softball field, a pair of tennis courts and the Winner Youth Bass Fishing Pond. Like many South Dakota towns, game around Winner is plentiful. “The hunting is very good out here,” Shipp says. “We have pheasant, turkey and deer, and there are even some people who hunt prairie dogs.” The Winner County Club spans a 9-hole course.
