Over the years, the station was known as Whyn (pronounced WIN) radio. As the eras passed in the rock 'n roll era, some of its monikers included CHANNEL 56; RADIO FIVE SIX OH; FIVE SIXTY W - H - Y - N; FUN FIVE SIXTY and THE BIG FIFTY SIX. Many jingles (mainly produced by PAMS) reflected these ongoing themes.

In the early '60s, WHYN was the dominant Top 40 radio station (competing with rival WSPR, which was on 1270 AM) with disk jockeys who were on the air for years. These included Phil D-e-e, Bob Allen (deceased), Bud Stone (deceased) and Little Davy Jones early in the decade. In 1968, the line up was Bob Allen (deceased), Lou Terri (deceased), Bud Williams, Ron Savage, Bob O'Brady (a/k/a Robert M. Kennedy - b. 1947; d. 31-DEC-2013 Salem, VA), Norm Lambert (deceased), Dennis Lee and Fred King. Additional DJs through the rock 'n roll era into the 70s included Jeff Baker, Larry Kruger (b. April 19, 1945 Savannah, GA; d. July 4, 2011 Swansea, MA), Jim Scott, Walt Cooper, Ken Moon , Patti Piech, Chuck Adams, Bill Erickson (who later was a news anchor at WHYN from 1990 through 2006), Ed Mitchell, Jerry Daniels, Gerry Tower, Rich Roy (who was also on WHYN-FM in their beautiful music days), Mike Taylor, Jackson Hill, Jungleman (Peter Pratt), longtime news legend Ron Russell, news anchor Tony Gill, who worked earlier at WBZ and WRKO in Boston, and others. In the '80s, DJs included Doug Hawkes, Charlie Donovan, Sherri McBride and Dan Williams (who later did mornings on WHYN-FM with his wife, Kim Zachery). Some early airchecks of the station are at Northeast Airchecks and ReelRadio.

The station programmed mainstream Top 40 until FM stations became popular. Automated WAQY (102.1 FM; branded Wacky Radio) went on the air in 1972 and cleaned WHYN's clock. In fact, Jim (James Marshall) Rising was WAQY's first Program Director (circa 1976) after they began live programming. Jim came over from WHYN, where he was their morning show jock, to program WAQY. He brought along WHYN's Johnny (Bekish) Michaels.

WHYN was the radio home for the Boston Red Sox until 2007 when WVEI-FM (now WWEI) took over. The station is now the highest-rated news station in the Pioneer Valley.

The station has undergone several ownership changes over the years starting with the Daily Hampshire Gazette; Guy Gannett Broadcasting (no relation to the present-day Gannett Company); Affiliated Communications (the broadcast division of The Boston Globe); R&R Broadcasting (Robinson & Reece); Wilks-Schwartz Broadcasting; and Clear Channel Communications (now iHeartMedia, Inc.).

The station was always the top rocker during the rock 'n roll era prior to the FM dial's domination. WHYN is also a heritage station with a lengthy history. Originally, the Hampden-Hampshire Corporation (a consortium of the Daily Hampshire Gazette, the Holyoke Transcript-Telegram, the Greenfield Recorder, and the Springfield Newspapers) owned WHYN-AM-FM-TV. The stations were sold in 1967 to Guy Gannett Broadcasting. WHYN and WHYN-FM were sold to Affiliated Publications in 1979; Guy Gannett retained WHYN-TV, which kept its original studio location and changed its call letters to WGGB-TV. The radio stations moved to downtown's "Marketplace" location, where they remain housed today along with sister station WRNX (Country).

WHYN partners with the area's CBS affiliate WSHM-LD for winter weather storm coverage and closings.

Programming