A Tranquil City In South Dakota Offers Retirees A Blend Of Rustic Charm And Modern Comforts​

About 160 miles from South Dakota's most populous city, Sioux Falls, sits the small-city charmer of Gregory. With a population of just over 1,300 people as of 2023, Gregory is the perfect tranquil city for any visitor seeking a calm getaway from the bustle of everyday life. It's also great for those who are ready to settle down in their retirement. Investopedia ranked it as one of the best midwest cities for retirees to head to when entering their golden years. Located where the U.S. Highways 18 & 47 meet, the city's charm is derived from scenic outdoor locations like the nearby Lake Francis Case, activities like golfing and hunting, and parks that are perfect for relaxing.

For travelers looking to visit Gregory, the closest airport is Pierre Regional Airport which is 122 miles to Gregory, but for anyone looking for an airport with international options then your choices are limited in the state — your best bet is to fly the state's largest airport, Sioux Falls Regional Airport. There you can find a connecting option to an international airport. Though the Mount Rushmore State has plenty of under-the-radar walkable cities like Vermillion, your best option when traveling to the city is to drive. Gregory is a small city so technically it is walkable, but if you're wanting to travel to nearby attractions like the South Dakota Hall of Fame (a museum honoring the notable figures in the state) or the Akta Lakota Museum & Cultural Center, then you'll need a car.  

Let's face it, home prices are high around the United States. As of February 2025 the median price for a house that has already been built is just over $398,000. Not cheap. But Gregory is one of the few places where renters and owners don't have to empty their bank accounts to reside there. Travel and Leisure lists Gregory as one of the most affordable cities to live in; the median cost of a home in the is under $130,000 and the price for monthly food expenses amounts to $645. It's no wonder it's a desirable destination for retirees, as South Dakota is one of the least expensive states in which to retire — plus, social security income is not taxed in the state. 

While the Mount Rushmore State is filled with plenty of attractive destinations and activities, including Mount Rushmore and seeing the sunrise at Badlands National Park, Gregory and its neighboring towns have a plethora of underrated destinations for visitors. For example, you could go golfing at the Gregory Golf Course. Open to golfers of every skill level, this 9-hole course has scenic views and all the good food and cold beer any golfer could want. Another option is to head to Gregory Buttes Observation Park. The park is home to a dedication wall which honors those who donated to help build the park that overlooks the city. The previously mentioned South Dakota Hall of Fame and Akta Lakota Museum & Cultural Centerare sites worth visiting, though they aren't directly in Gregory. About 60 miles away from Gregory is the majestic site of Dignity: Of Earth and Sky, also known as the Dignity statue. The stainless steel sculpture stands 50 feet tall and overlooks the Missouri River. It's a must-see for any visitor to South Dakota.

South Dakota has many wonderful places to stay, including the scenic State Game Lodge, the oldest and largest resort in Custer State Park. In Gregory, there are several places to stay, including the Gray House Motel along E Highway 18, which has rooms equipped with queen size beds. To get price ranges you'll have to call the motel directly. The AmericInn by Wyndham Chamberlain Conference Center is about 60 miles away from Gregory on East King Street. The hotel is situated along the Missouri River where visitors can easily access scenic spots for fishing and hunting. Rooms go from $142 and up there.

Gregory has some solid options for visitors looking to dine out. On Main St. there's Homesteader, a delightful steakhouse where they not only serve up steak and prime rib, but other menu items which include noodle stir fry, egg rolls, and more. If you're craving some good cheesecake after chowing down on a classic cheeseburger, then Sissy's Cafe, also on Main St., is your place. Sissy's serves up breakfast items like waffles and omelettes and they also offer an array of American and Mexican cuisine that includes chimichangas, burritos, smoked brisket, and surf & turf burgers to name a few.