The first issue of Outbound Magazine appeared in August 2002 printed on glossy magazine stock and in convenient pocket size. While some refered to it as the new "bar rag" (a term based on a long-ago Milwaukee activity guide called RAGG), the magazine featured articles, news, and activity calendars. The magazine was a much needed venue for businesses to run glossy color advertisements, a capability never previously available to LGBT businesses in Wisconsin. The magazine was the brainchild of lovers Jim Dawson and James.

Outbound magazine had an excellent regular feature, in virtually every article, which focused on a particular organization or business (usually bars)- typically featuring same on the cover, and having a brief article inside about that organization or business. This had the effect of giving various groups and businesses exposure they might not otherwsie have.

Starting with volume 3 issue 8, the magazine's name printed on the cover was changed from "OutBound Wisconsin" to "OutBound Midwest", reflecting their desire to also cover bar activities in northern Illinois and especially Chicago. Starting with volume 4 issue 1, the magazine was named simply "OutBound Magazine" on the covers.

The publishers of Outbound briefly also published a monthly newspaper, Outbound News, to attempt to fill the gap left with the demise of the In Step newspaper a few years before. Unfortunately, in the same month they launched that paper, another newspaper also started up. Outbound News was folded one year later, to allow the staff to focus on maintaining the high quality of the monthly magazine and web site.

Publishing of those two separate magazines ended in December 2011. Beginning with the January 2012 issues of Quest, OutBound Magazine was merged into that publication, with Quest converting from a combination of matte and glossy pages and becoming 100% glossy pages, and incorporating the various OutBound features as well. OutBound ceased to exist as a separate publication.