WaKeeney shines brightest during the holidays, when its four-block downtown beams with lights, garlands and its centerpiece 35-foot-tall tree. The “Christmas City of the High Plains” cranks up the wattage the Saturday after Thanksgiving, but the festive spirit lingers beyond the season at North Pole Park. Candy canes lead into the alleywide space, perfect for selfies with

Before your polar explorations, visit family-owned Hometown Bakery for a full spread of morning options that includes cinnamon rolls and breakfast burritos made with from-scratch tortillas. Later in the day, you’ll want to make room for the prime rib, hand-cut steaks and hand-pattied burgers at Western Kansas Saloon and Grill. The original wood floors and tin ceiling remain in the restored, century-old hardware store. Also look for paintings by local artists that portray the region’s past. 

On the east edge of town, the Trego County Fairgrounds buzz with the 115-year-old Trego County Fair in July, then switch gears for races at WaKeeney Speedway. On many Sundays from March through September, stock cars and other speedsters fly around the 3/8-mile dirt oval, with special sprint car races revving up for fair week. Also at the fairgrounds, a 50-foot-long mural within the Trego County Historical Society Museum depicts buffalo, railroad, Native American and covered wagon scenes as a nod to the region’s rich history. Fossils, military displays, farm equipment and a 1910 one-room schoolhouse round out the history lessons at this museum, proving that there’s much to learn and discover beyond the holiday season.

TRIP TIP

A visit to Israel’s Shiloh wine region inspired a Kansas couple’s dream: to bring winemaking to the western Kansas plains. On a century-old family farm southwest of WaKeeney, Shiloh Vineyard and Winery turns homegrown grapes and apples into red, white, fruit and dessert wines. Sip some at the gabled barn and chicken-coop patio, then take a vineyard tour and overnight in a converted shed.

Shiloh Vineyard (Doug Stremel)

Discover more of the Sunflower State’s magical Main Streets in the 2025 Official Kansas Travel Guide.