WKFY signed on the air on August 16, 2013; 11 years ago (August 16, 2013). It originally broadcast at 98.7 MHz. It began with a stunt loop of "Old Cape Cod" by Patti Page. The official format debuted on August 19.[3] The format is designed to include "oldies, classic album cuts and modern artists loved by older listeners."[4][5] On June 9, 2014, WKFY extended its signal with the use of translator W263CU (100.5 MHz) in Hyannis, fed from WKFY's 101.5 signal. A second translator, W278DW (103.5 MHz) in Vineyard Haven is fed via 102.9 WPXC-HD3.[6][7][8]
On February 19, 2020, WKFY moved from 98.7 to 101.5 MHz while also moving to a new transmitter site in Orleans. The effective radiated power (ERP) increased from 3,200 watts to 6,000 watts. The height above average terrain (HAAT) was raised from 47.3 meters (155 ft) to 87.3 meters (286 ft), improving Koffee FM's signal in the Outer Cape. Two FM translators also began carrying WKFY, helping to boost WKFY’s coverage area in the Upper Cape, Mid-Cape and Martha’s Vineyard.[9]