Anthony Smallwood’s leading what would seem to be an uphill charge. He’s trying to make downhill skateboarding as much a part of Adams Morgan Day festivities as chicken kabobs.

Smallwood envisions a gang of the world’s most renowned downhillers—folks who can stay on their boards while gravity takes them upward of 60 miles per hour—assuming control of the grassless knoll just east of Meridian Hill Park on 15th Street for a day. He swears it’s not a pipe dream.

When not at work as a customer-service agent for a major airline, the 35-year-old Adams Morgan resident can likely be found barrelling down the steepest city streets on his board. Looking for like-minded daredevils, a few years ago Smallwood founded the D.C. Downhill Club.

“The club is a group of people who just love going really fast,” Smallwood tells me, just after completing a ridiculously rapid run down an almost rustic lane off Embassy Row. “You have to do it to understand how hard it is to just stay on the board.” (At Smallwood’s request, the name of his hidden jewel of a downhill route, which he says provides the best combination of speed and safety in Northwest D.C., will not be mentioned in this article.) What with his leather jumpsuit, gloves, and helmet, only his $300 board and hip skips—from Vans, a company that has long had a stranglehold on the skater footwear market—give away that he’s not a motocross rider.

Away from D.C., Smallwood has made several friends among the cream of the skateboarding crop. He met them by entering competitions on the professional skateboarding tour, held almost exclusively on the West Coast. In these events, Smallwood was usually the only entrant from east of the Mississippi.

“I’ve had to pay a lot of money to be a pro athlete,” Smallwood says with a laugh. The major allure of his day job, Smallwood admits, is that it facilitates his travel to out-of-town skateboarding destinations.

Earlier this year, Smallwood invited some tour stars to bring their speedboards to his neck of the woods in the name of growing the sport. Several of the top names—including underground heroes with handles like Biker and Leemo—RSVP’d in the affirmative. So in March, Smallwood approached organizers of the Adams Morgan Day Festival and proposed adding a skateboarding race to the agenda.

“I’ve never organized any kind of event in my life,” he says. “Putting on something like this is kind of the antithesis of skateboarding. But I love D.C., and I love downhill, and I wanted to just put my two loves together.”

At first blush, it doesn’t seem like a very good fit. Skateboarding is hardly indigenous to Adams Morgan, or any other part of D.C., after all. It was invented in California in the late ’50s as a way for surfers to work out their jones when they couldn’t get to the waves. While so many other rad fads have come and gone, skateboarding has remained an edgy, scare-your-parents piece of pop culture.

Then again, D.C. isn’t the birthplace of the chicken kabob, either. Smallwood soon had festival organizers as enthusiastic about the race proposal as he was.

“We jumped at the idea, really,” says Tom Oliver, director of Adams Morgan Day. “I like it that [Smallwood] and the downhill club are headquartered in Adams Morgan, that this is an event that can take place right here, that skateboarding fits in with the character and attitude of the neighborhood. I think this could be great.”

Oliver was so enthused, in fact, that he moved the entire festival to a date two weeks later than originally scheduled, just so it wouldn’t conflict with the professional skateboarders’ tour. Adams Morgan Day now falls on Sept. 16 and 17, one of the few open weekends of the downhill season.

Now all Smallwood and the Adams Morgan Day organizers have to do is convince the D.C. government that the race is worth closing a street for.

“I think we’ve got a great shot at it,” says Smallwood.

Adolescents have always made up skateboarding’s major constituency, mainly because the sport lends itself to young bodies that will bend and not break during the inevitable impacts with terra firma. (Smallwood, with the fragility that comes with age, has had shoulder and hernia surgeries in the last year and a half because of spills.)

Because it is primarily a kids’ avocation, skateboarding proponents have never been able to mount much of a fight when local lawmakers have implemented rules or outright bans against it. And over the years, Washington has earned a reputation as one of the least skateboarder-friendly towns in the country.

Check out this Washington, D.C., entry from a national skateboarders’ directory: “Skating in D.C. is now a bust. Cops will arrest you and they will ticket you [at] any federal building or monument.”

But the advent of competitions like the X Games and Gravity Games, which are sort of olympiads for “extreme” sports, has brought money, television, and adults into skateboarding. Smallwood has referenced all of the above while lobbying the powers that be in the city to sign off on his Adams Morgan Day race. He has pointed out that if the event comes off well, D.C. could become the first East Coast stop on the professional downhill tour.

And he’s learned the verity of the first law of advocacy: Money talks.

“My theme is that the city would really like to get the Olympics here in Washington, and what I want to do is get the Gravity Games here first,” Smallwood says. “The site of the Gravity Games will be open next year, and getting them here would be great for the city. I want [Adams Morgan Day] to be the springboard for that. The new [mayoral] administration seems very open to anything that will show off the city, and I’m amazed how great people with the D.C. government have been so far. No matter what reputation the city government has, it’s been a pleasure to work with them so far.”

Oliver, too, is bullish on the Anthony Williams administration. If the Adams Morgan Day organizers can show the government it will pay for the city services needed to put on the race (“about $10,000 to $15,000,” says Oliver), he’s convinced police barricades will be put up along 15th Street on festival weekend for all the right reasons. Oliver is hosting fundraisers, including a DJ competition at Cities, to raise the lucre necessary to see it through.

Showing savvy that belies his inexperience as a promoter, Smallwood hasn’t let the slightest doubt about whether the race will actually come off trickle down to the invited talent.

“I already got my West Coast boys to buy their tickets, and they’re coming here to race,” he says. “So if everything I’ve been working on falls through, well, there won’t be a race on 15th Street. But we’ll take it underground if we have to. There’s going to be a race in D.C.” —Dave McKenna