The 2000 festival was headlined by Rage Against the Machine and Stone Temple Pilots with a half-hour documentary produced by Washington, D.C.–based TV station MHz Networks and hosted by WHFS on-air personalities.

The strong ticket sales of the previous few years' festivals inspired the station to expand the HFStival, beginning in 2001, into a two-day event; between May 27 and 28, including over 40 artists.

The incident cast doubt on whether the event, or the second day, would be allowed to continue – especially in light of the negative publicity the venue received when a concertgoer was hospitalized after a lightning strike at the 1998 Tibetan Freedom Concert.

Lagging ticket sales seemed to threaten the festival's future for a while, first when it was reduced for 2003 from two days back to one, and again when a planned second Fall Edition was cancelled following a scheduling conflict that required a change of date and venue.

In early 2005, the station abruptly went off the air, replaced by a Spanish language Latin pop format, and listeners feared the HFStival's days had come to an end.

HFStival 2005, held at Baltimore's M&T Bank Stadium, was notably different from previous affairs, featuring a lineup of artists from all points of the station's long history: original punk rockers The New York Dolls shared a stage with hard rock icon Billy Idol, veteran alternative band They Might Be Giants, and current rising stars like The Bravery.

[4] On June 5, 2024, the social media accounts for the 9:30 Club and Nationals Park posted a teaser image that indicates the HFStival would return on Saturday, September 21, 2024, at Nationals Park in Washington, D.C.[5] On June 11, 2024, the official lineup and tickets for the September 21, 2024, show were released; performing artists were announced, including The Postal Service, Death Cab for Cutie, Incubus, Bush, Garbage, Jimmy Eat World, Girl Talk, Violent Femmes, Tonic, Filter and Lit.