In October 2017, Waltrip had plans to attend the Route 91 Harvest music festival, but he canceled those plans. Later that night, a gunman, Stephen Paddock, fired shots at the festival from the 32nd floor of the Mandalay Bay hotel and casino, causing the deadliest mass shooting in U.S. history. The following morning, Waltrip revealed on his Instagram account that he had befriended a family while in Las Vegas earlier in the day, that were also scheduled to attend the festival. On October 4, he tweeted that he had contacted the father of the family, adding that they "are doing as well as could be expected."