Harbor Room opened as a bar tucked just off South 1st Street, about 6 blocks south of the major bar area- and its main competition, the Boot Camp. The Boot Camp had been the city's sole levi/ leather bar for some years, and was becoming crowded and a bit "tired" for some people. Parking around the Boot Camp was also becoming more difficult. The time for another Milwaukee leather bar just seemed right.

Harbor Room is housed in an historical building, mid-block. Almost kitty-corner to the Allen Bradly complex, and largely surrounded by Grede Foundry, the bar was popular almost immediately, and in short order was filled to capacity late on Friday and Saturday nights. The owner (Gregg Fitzpatrick) and his partner (Eddie) moved in above the bar, and they and their dog were seen regularly. Soon after opening, a patio was opened outside, about 50% larger in size to the inside area of the bar- used for cookouts and general customer appreciation of the weather. A raised section was built as well, and used for shows (especially the annual Mr. Harbor Room contest).

Harbor Room has been innovative in several areas. For one thing, they open early in the morning: initially at 8:00am, and later opening at 7:00am each day. Surprisingly to some, they have seen good business with their early hours, as the only gay bar open when 3rd shift employees get off work. The patio also has extended use: while some bars close their patios during the winter, the Harbor Room patio is open whenever the bar is (a porta-toilet added to the back of the building, coupled with the always-open patio, legally doubles their occupancy limit). They have regular drink and bar specials- most notably "half price drinks for men without shirts- all the time". They serve free pizza during happy hours daily.

An election is held each anniversary for the Mr. Harbor Room title-holder (see the Images page for the list of title-holders and photos.)