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The Amazing High Heel Race to help fund huge gay pride flag for Hillcrest

SAN DIEGO -- While Hillcrest is widely recognized by locals as San Diego’s gayborhood, Stefan Chicote, owner/partner of Gossip Grill and Baja Betty’s, has long lamented the fact that tourists seem unaware of his neighborhood’s defining demographic.

So, in an effort to promote a “more colorful Hillcrest,” or, as Chicote put it, to “gay it up,” he is organizing an event with the Hillcrest Business Association to both beautify and “brand” Hillcrest.

Proceeds from The Amazing High Heel Race on June 18 will help fund the erection of a 65-foot gay pride flag at the east end of Hillcrest where Normal Street begins, a monument Chicote hopes will serve as both an emblem of pride for residents and a welcoming beacon to outsiders.

“The flag will be an enduring symbol of the importance of the LGBT community in the past, present and future of Hillcrest,” said Johnathan Hale, president and CEO of Hale Media and co-chair of the Pride Flag Project. “For miles around people will be able to see this symbolic flag, a symbol of pride for those of us who live and work in the neighborhood, and a symbol of solidarity against any group seeking to strip us of our basic human rights.”

But aside from the project resulting from the event, the real excitement will be in the event itself.

The Amazing High Heel Race is indeed a race on high heels, but it will also function as a scavenger hunt, enlisting the help of several local businesses. Participants in teams of six (four minimum) — encouraged to dress up in a team theme — will scamper from business to business based on a set of provided clues and perform scavenger challenges, all in heels no shorter than three inches (and yes, there will be someone measuring).

The clues will not be inordinately difficult to figure out, but Chicote agreed that Hillcrest residents and others familiar with the area will have an advantage.

The starting line will be at Baja Betty’s, and Urban Mo’s will host an obstacle course in the middle of the race. Afterward, teams can relax and celebrate during a closing party at Gossip Grill, featuring food and drinks in the parking lot while a DJ spins tunes inside.

Prizes will be given for Best Time, Highest Heel, Fiercest Heel, Most Creative Team Attire, Best Team Spirit, and, for the high heel rookies, Biggest Blister.

Participants of all stripes are welcome, but everyone is expected to compete on their best behavior — according to the official race rules, hair/weave pulling and wig snatching are strictly prohibited, and outside booze is not allowed.

Anyone interested in joining the race — participants and businesses — has until June 11 to register, and Chicote encourages those interested to sign up soon — “the sooner, the better,” he said.

Volunteers are also needed for duties such as forming pep rallies along the route, guiding racers across the street, and holding up the finish line sign. Registration forms for all levels of participation (plus the full set of rules and other useful information) are available on the event website.

Hopefully, the first-time event will catch on for years to come, as Chicote has other beautification projects in mind. Next year, he would like to use funds to paint each light post in Hillcrest a different color of the rainbow, so “the streets are tastefully lined up,” he said. Eventually, he’d even like to add low-key touches, such as baskets of succulent plants hanging from the buildings.

But for now, the focus is on funding that enormous pride flag, which, if it’s visible from planes and skyscrapers as Chicote expects, will remove all doubts as to where San Diego’s gay-friendliest area can be found.

“Currently, we do not have a public monument we can all point to and say ‘that's ours’,” said Michael Brennan of Urban Green, the Pride Flag Project landscape architect. “There is a great need for such a prominent public gathering place where we can unite and celebrate our past, present and future, and hopefully this flag will serve as a beacon to the entire community for generations to come.”

Just a few years ago, the idea of creating a space for the largest pride flag in the city was just a vision, said Ken St. Pierre, director of sales and business development for Hale Media. “But thanks to Johnathan, Stefan and all the people volunteering for The Amazing High Heel Race, the vision is becoming a reality,” he said.