Photo by James Calder.

Tonight will certainly be a fantastic night to celebrate one of the District’s most endearing Halloween traditions: the High Heel Race.

At 9 p.m. this evening, hundreds of drag queens will don their finest dresses and costumes, strap on two-inch heels and race down 17th Street in front of a crowd estimated to reach into the tens of thousands. As Metro Weekly reported a few years back, the race started in 1986 in a somewhat impromptu fashion:

No one owns the High Heel Race, a D.C. institution begun years ago as Parson explains: a spontaneous competition of drag queens running the two blocks from JR.’s Bar & Grill at 17th and Church streets up to Annie’s Paramount Steakhouse, where they would down a shot, and then race back. According to a timeline on Rainbow History Project’s website, the High Heel Race was first run in 1986. That year’s winner, Clinton Winter, received a bottle of champagne for his efforts.

One of the most infamous runnings of the race may have come in 1991, when police arrested six people for disorderly conduct, provoking complaints from the gay community. (The Metropolitan Police Department’s Gay and Lesbian Liaison Unit wasn’t created until nine years after the incident.)

This year, for the race’s 25th anniversary, Mayor Vince Gray and Councilmember Jack Evans (D-Ward 2) will serve as Grand Marshals. 2011’s race also marks the last year that David Perruzza, general manager of JR.’s Bar & Grill, will oversee it. (Next year, Historic Dupont Circle Main Streets will take over the organizational reins.)

If you want a good viewing spot, you’d best get there early — especially on an evening set to be in the mid-50s.