Brannon was staying at the Sunshine Inn Hotel on US Highway 90 east in Live Oak, Florida on the night of July 14/15, 2020. She and her boyfriend, Eddie Emerson, had been traveling from Micanopy, Florida to Detroit, Michigan in separate cars with all their belongings, including a dog and eight chickens
After an argument, Brannon left the hotel room but continued contact with Emerson with text messages. At 10:30 p.m., he went outside to check on her and found her drunk and crying outside the hotel. He took her car keys away from her so she wouldn't drive under the influence. Just after midnight, she texted him, threatening to leave him. She said she was taking her car registration, a bag of clothes and her guitar. Some witnesses at the hotel stated that Kelley was seen walking away from the hotel on US Highway 90 headed East. She was stated to have had her guitar in a case over her shoulder as she walked away. She has never been heard from again. Her purse, money, identification and other belongings were left behind at the hotel inside her unlocked car, but her phone and guitar were missing. Although Brannon frequently traveled and had friends all over the country, she always stayed in touch with her mother, who lives in New Hampshire. Because her mother hasn't heard from her since her disappearance, Emerson and Brannon's family are concerned for her welfare and fear something bad has happened to her.