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The frequency of 107.9 MHz was originally assigned by the Federal Communications Commission to Westport, Connecticut under its Table of Allocations, and in 1962 the signal which was later to become WEBE signed on the air as WMMM-FM.

From 1970 through 1984 the station, then known as WDJF, was owned by Donald J. Flamm and affiliated with Westport radio station WMMM AM 1260. The stations broadcast out of offices and studios located above a deli at 163 Main Street in Westport. The broadcasting antenna for 107.9 was located in a residential zone in Wilton, Connecticut, to the chagrin of neighbors, and the height of the antenna was only 135 feet, so the broadcasting radius of the station was quite small.

In 1984 New York entrepreneur Franz Allina, who also owned WBAB and WGBB, purchased 107.9 WDJF for $2 million and hired Vincent Cremona, General Manager of Bridgeport station WICC to run it for him.

A call letter change was needed, so various lists of unused call letters were studied by station management, yet none seemed to work, that is until Cremona's 14-year old son, Vinny, found "WEBE" on the list, and ran around saying "Wee Bee Wee Bee Wee Bee". Based on this example of powerful appeal and figuring these to be memorable call letters, the call sign WEBE was applied for to the FCC and granted in 2/84. "WEBE108" signed on the air at midnight on March 1 of 1984. Curtis W. Hansen, former Program Director of WAVZ and WKCI in New Haven was hired to program the new station.

WEBE108 moved to 50 Washington Street in Norwalk, 10th floor, and in the fall of 1984 moved to the 11th floor of 50 Washington Street. The station's target was female baby boomers, the idea being to latch on to the 'baby boom' generation, the population bulge, supersatisfy them, and grow older as they did. The station 1st slogan was "Hits Of A Whole Generation", playing the most popular hits from 1963 (the Beatles invasion) to the present day.

In 1985, after months of hard work and technical exploration by owner Franz Allina and consulting engineers, WEBE moved its transmitting antenna to the top of the United Illuminating red and white smokestack in Bridgeport harbor, putting out a full 50,000 watts from a height of 386 feet above average terrain.

In 1987 the station was sold to ML Media Partners, led by New York television executive Marty Pompadur and partners, for the sum of $11 million.

In 1989 ML Media partners also purchased WICC (AM) in Bridgeport for $6 million.

In 1990 Cremona moved both WEBE and WICC together under one roof at 350 Fairfield Avenue (2 Lafayette Square) in Bridgeport, Connecticut.

In 1999 the stations were sold for $66 million to New Canaan radio operator Frank Osborn and partners (including Cremona), who in turn sold the stations, along with additionally acquired clusters in Danbury, Westchester, and Poughkeepsie, New York, to Cumulus Media in 2002 for just under $300 million in cash and stock. Under Market Manager Ann McManus, the stations continue to be popular and profitable. HD radio.

Cumulus Broadcasting began upgrading its stations to HD Radio broadcasting in 2005. One of the first ten stations to be upgraded was WEBE.