1994
August: With a staff of three, Watermark publishes its first 24-page issue featuring Winter Park’s Amanda Bearse (Married With Children) on the cover.
1995
August: Todd Simmons signs on as editor as Watermark expands to Tampa Bay.
1996
May: Watermark grows to 60 pages, begins printing in four-color process and features its first national advertiser—Miller Brewing.
1997
June: Watermark produces the first large-scale nighttime party during Gay Days Weekend as more than 2,500 attend Beach Ball at Typhoon Lagoon.
1998
April: Watermark introduces a new tabloid-size magazine format and introduces a distinctive “W” masthead logo.
June: Watermark obtains permission to hang rainbow flags throughout downtown Orlando during Gay Pride Month. Televangelist Pat Robertson predicts doom, and the ensuing debate mobilizes the city’s LGBT community.
September: WatermarkOnline.com debuts.
1999
June: With 5,500 attendees, Beach Ball at Typhoon Lagoon sells out.
October: Watermark purchases and relocates to an office complex in Orlando’s Colonialtown South area. The newspaper also opens Tampa Bay offices at the Suncoast Resort.
2000
April: Watermark expands coverage to the Sarasota/Bradenton area, increasing circulation to 18,000 every two weeks.
May: Watermark produces its first glossy guide to Gay Days Weekend.
2001
March: Watermark hires Scott Smith as its first full-time editor.
September: Watermark Entertainment Group, Inc. (WEGI) produces comedy shows during Gay Days Weekend and TIGLFF. After 9/11, two more planned events are canceled.
November: The Watermark Awards for Variety and Excellence (WAVEs) debut.
2002
February: Watermark sells Beach Ball to Mark Baker Productions.
March: Watermark acquires publication rights to Celebrate! in Key West, and names former contributor Mike Kilgore editor.
2004
September: Watermark commemorates its 10th anniversary the night before Hurricane Jeanne—the third hurricane of the summer—hits Orlando.
2005
May: Watermark hires Steve Blanchard as its first full-time Tampa Bay bureau chief.
September: Watermark sells Celebrate! to a local publisher in Key West.
2006
October: Editor Dave Weithop dies unexpectedly of a cancerous brain tumor.
2007
June and September: Watermark publishes its first programs for St. Pete Pride and Orlando’s Come Out With Pride.
October: Watermark brings rainbow flags back to downtown Orlando for Come Out With Pride.
2009
January: Watermark lays off four staff members after the recession causes a 35% reduction in ads—mostly real estate. Publisher Tom Dyer resumes editing the newspaper.
May: Watermark hires Jamie Hyman as online editor for a redesigned WatermarkOnline.com.
June: Steve Blanchard is promoted to Watermark editor.
2010
June: Watermark joins with Mark Baker to produce Stratosphere at Universal Studios during Gay Days Weekend.
2011
June: Watermark joins with AlandChuckTravel.com to produce Fire & Ice Weekend at the Postcard Inn during St. Pete Pride.
2014
January: Tom Dyer’s “I’m Sorry” interview with Charlie Crist goes viral, trending on HuffPost.com, MSNBC.com, CNN.com and other national media.
August: Watermark publishes the 25th anniversary program for the Hope & Help Center’s Headdress Ball in Orlando.
September: Watermark celebrates its 20th anniversary. Founder and owner Tom Dyer promotes Rick Claggett as publisher.
