In 1933, Callaway’s first Pioneer Picnic was held in connection with the dedication of the first Custer County Courthouse in Morgan Park. The annual celebration has been held every year since, except during World War II.
The Pioneer PIcnic has been a two-day event nearly every year since its inception. In the early years, most of the platform programs that have always been part of the celebration featured politicians - but after several years that gave way to featuring local talent. A parade, races, baseball games, band concerts and dances were also part of the early days of the event and many of those continue today.
Horse shows, and 4-H club livestock, sewing and homemaking and a flower show were later added to the festivities. Over several years the Callaway Chamber of Commerce added such extras as the crowning of a queen and a free barbecue. The carnival also came to town with their rides and sideshows.
In 1938, the community celebrated the 50th anniversary of the incorporation of the Village of Callaway, and that year one of the largest crowds in history was in attendance for the Pioneer Picnic. A special program under the direction of W.F. Haycock was held honoring the pioneers, with 250 registrants. Highlights from the special celebration included an address from Nebraska Gov. Roy L. Cochran, a performance by the Broken Bow American Legion drum corps, and music by the Callaway band.
Afternoon activities at the 1938 gathering included ball games and races of all kinds, and various political candidates presented speeches during the evening. Mark Schneringer was the only living member of the first Village Board at that time, and was the guest of honor for the celebration. 
The main feature of all of the Pioneer Picnics had been the “registering” of the pioneers. In 1939, there were 284 pioneers registered, and by 1966 there were only 23.
The Pioneer Picnic is always celebrated the last weekend in June, and is organized by the Chamber of Commerce in conjunction with the Alumni Association banquet and program. The Seven Valley’s Rodeo Association also hosts a two-day rodeo and trail ride events that weekend, which this year will be June 24-26.