The "Winter Dance Party" tour perform at the Surf Ballroom in Clear Lake, Iowa. The admission price is upped to $1.25 from its normal $.75. They arrive at the ballroom at 7:30pm and have to perform at 8:00pm. Buddy makes arrangements to charter a small plane after the dance to take him and his band to Fargo so they can rest and do their laundry. In the show, Frankie Sardo opens with "Fake Out" and is followed by the "Big Bopper" who does "Chantilly Lace". Then Ritchie Valens comes on and does "Come On Let’s Go", "Donna" and "To Know Him Is To Love Him". He closes the first act with "La Bamba". At this point, according to Mason City radio station KRIB DJ Bob Hale, the following happens backstage during intermission. Ritchie begs Tommy Allsup to give up his plane seat. After arguing to no avail, he says, "I’ll tell you what. Let’s flip for it." Tommy agrees. Neither has a coin in their stage clothes pockets, so Bob Hale says, "I have a quarter, Ritchie. You call it." Ritchie says, "Heads." Hale flips and it is heads. He says, "OK, Ritchie. You’re flying." Years later Allsup opens a bar calling it the "Heads Up Saloon" in honor of his lucky coin toss. Dion opens the second show or "act". He does "Teenager In Love", "The Wanderer" among other songs. Buddy goes on the stage and does "Gotta Travel On", "Peggy Sue", "That’ll Be The Day", "Rave On", "Heartbeat" and "Everyday". (Not necessarily in that order.) The other numbers are not known. At the end of the show, Buddy calls Ritchie and the "Bopper" back on stage to sing "Brown-Eyed Handsome Man" together with him. Ritchie closes the show with a repeat of "La Bamba". It is midnight and the dance is over.
After the dance, bassist Waylon Jennings gives his seat to J.P. Richardson, who had the flu. Waylon jokes, "I hope you crash!" The plane takes off in a snowstorm from Mason City, Iowa. Buddy Holly, Ritchie Valens, J.P. Richardson and the pilot, Roger Peterson, are killed when their small Beechcraft Bonanza plane crashes into a field outside of Clear Lake, Iowa. The plane, chartered through Dwyer’s Flying Service in Mason City, Iowa, was simply a small red and white single engine four-seater Beechcraft Bonanza. Its wing had the registration number, N3794N on it. They left the Mason City Municipal airport shortly after 1 a.m.
From the Mason City paper is the following report: "The plane crashed about seven miles northwest of the airport. The trip to Fargo was expected to take about 3 1/2 hours. When no word of the plane's arrival was heard, Jerry Dwyer, owner of the flying service, set out to look for the party. He was delayed several hours because of early morning fog. Dwyer discovered the wreckage on the Albert Juhl farm at about 9:30 a.m. It was obvious that the pilot had been flying on a straight northwest line and was at a very low angle to the ground when he hit. The field slopes slightly toward the northwest. The left wing of the plane seemingly struck the ground and plowed a furrow for about a dozen feet before it crumpled and the body of the plane hit. It dug a shallow depression in the stubble field and the wing fell off as the rest of the plane bounced. It struck the ground again about 50 feet farther northwest and then skidded on the ground about two city blocks until it piled up against a fence. The wreckage was a jumbled mass, which would not have been recognized as a plane. Along the skid path small bits of the plane and its contents were strewn. There was a man's shoe, a traveling bag and small pieces of the plane, including parts of the instrument panel. The bag was the largest piece except for the wing, the jumble against the fence and three bodies. One body was broken and entangled in the wreckage. Two bodies were lying about 12 feet south and southwest of the plane. Another body was lying about 40 feet northwest of the plane. No bodies were positively identified at the scene. Newsmen and others were barred from the scene until 11:30 a.m. after Dr. Ralph E. Smiley, acting coroner, arrived. Authorities do not yet know the cause of the accident. Some believe, however, that ice may have formed on the wings or windshield making a forced landing necessary. Dwyer said he didn't have the ‘faintest idea’ why the plane crashed. He said the craft was in good condition. He said Peterson was a competent pilot and weather conditions were favorable for flying. He estimated that the plane crashed only "a couple of minutes" after taking off. Dwyer said that Peterson did not file a flight plan. Dwyer became worried when Peterson failed to report back from Fargo and checked other airports in Iowa, Minnesota and the Dakota area. The bodies were taken to funeral homes in Clear Lake. Two investigators from the Civil Aeronautics Administration were sent from Des Moines to investigate the cause of the accident. The booking firm said when other artists heard of the deaths, they volunteered to keep the tour going. These included Bill Haley and his Comets, Bill Parsons, and Frankie Avalon - all rock 'n' roll favorites."