Watermark Media was founded by Tom Dyer in Orlando in 1994, and expanded to Tampa Bay in 1995. Dyer is an attorney, former board member of the Metropolitan Business Association and Tampa International Gay & Lesbian Film Festival, and current advisory board member of the Harvey Milk Foundation.

In 1997 Watermark produced Beach Ball at Disney’s Typhoon Lagoon, the first large-scale nighttime party associated with Gay Days Weekend. Watermark publishes a glossy guide to that event – largest annual LGBTQ gathering in the nation – as well as programs for a Wedding Guide in May and Orlando’s Come Out With Pride in October.

Watermark was a newsmaker in 1998 when it sought to hang rainbow flags throughout downtown Orlando during Gay Pride Month. The city reluctantly acquiesced, but the controversy made national news when televangelist Pat Robertson predicted Orlando would be beset by hurricanes as punishment.

Watermark prints up to 20,000 copies every other Thursday, and distributes them in more than 500 locations throughout Orlando, Tampa Bay, Sarasota and throughout the state. The newspaper donates more than $200,000 annually in free and sponsor advertising to worthy local and national LGBTQ non-profits.

Watermarkonline.com was launched in 1999. The award-winning newspaper currently maintains offices in Tampa Bay and Orlando and employs a full-time staff of 12, along with several part-time and freelance contributors.

Watermark Publishing Group, founded by publisher Rick Todd, purchased Watermark in January of 2016.  Rick Todd is a long-time employee of Watermark Media and former board member of both the Metropolitan Business Association and Come Out With Pride.