The Dry Dock, connected to Four Season's Resort offers a simplified menu, but consistent delicious food. One of the few restaurants on West Lake Okoboji, the Dry Dock offers up legendary breakfasts, great lunches and dinners, and the local favorite Friday Night Fish Fry. Sit inside or out after arriving by foot, car, or boat.

Founded in 1960, the Three Sons has been a staple of Milford, IA retail. From Herman and Emil Richter, owners, was born the University of Okoboji, a ficticious university that calls the entire Iowa Great Lakes the campus of the U of O. Part of the experience of shopping the three sons, if walking the old battered floors, and taking a trip upstairs for half price, plus a buck. Brands you would expect in Milford Iowa are abundant, such as Patagonia, Oakley, Under Armour, Tommy Bahama, and more. There are currently 2 other stores; one at the amusement park, and another near the Regal Beagle called the bridge store. No self-respecting visitor to Okoboji leaves without visiting one of their stores.

Haywards Bay on West Lake Okoboji boasts low approaches and one of the few areas on West Lake to offer sand beaches. Renowned for the "bay of the flags", you will know you are in Haywards bay because of the all the American flags on the end of the docks. Fishing is great in Haywards Bay and the sunsets are one in a million. To get to Haywards Bay by car, one would drive the east side of the lake on Lakeshore Dr.