Eight Segways roll down the bike lane in the middle of Pennsylvania Avenue NW, each one piloted by a tourist in shorts and a helmet. An ear piece curled around the right ear of each rider delivers commentary just audible over the noise of rush hour traffic zipping by both sides of the procession.

“To your left is the J. Edgar Hoover building,” says the voice of the tour’s guide, a serious young man with the logo of his employer, Segs in the City, stitched on his pink polo. He points out that the building is “pretty ugly.” Cyclists weave around the tour as the facts keep coming: This is the National Gallery of Art, which has no right angles; this is the Stephenson Grand Army of the Republic Memorial, of which there is nothing interesting to note—but it’s on the ride from Segs in the City’s kiosk to the Capitol, and thus must be identified.

As the group trails him through the Capitol Grounds, the guide unleashes a flurry of information about landscape architect Frederick Law Olmsted. Next comes a lengthy narrative about the War of 1812, delivered on the east side of the Capitol.

It’s possible that some of the Segway riders are listening, but their behavior indicates otherwise. While the guide stands on his Segway and describes the missing cornerstone of the Capitol building, his flock zips around the pavement, snapping pictures and trying out turns on the Segways. One Russian woman, who needed translation during the pre-tour Segway training session, laughs maniacally and performs one loop after another as the guide explains that the current Capitol dome is larger than the original. The guide’s jokes, including one about D.C.’s most beloved building—it’s the IRS building—win little reaction from the Segway riders.

For a tour that bills itself as “exhilarating” and takes its winking name from a TV show about single ladies having sex in a city, this one-hour Taste of D.C. Safari from Segs in the City is remarkably staid—the unsexy, unscandalous script would sound familiar to anyone who passed eighth grade American history. To an unsuspecting eye, this tour looks like any of the many Segway groups puttering around town, irritating pedestrians and bicyclists, and looking slightly foolish as the riders digest information about President William Henry Harrison’s fatal decision not to wear an overcoat during his inaugural address.

Against this benign background, a real scandal of sorts is unfolding. Segs in the City offers daily tours of a city that requires its tour guides to be licensed, and the company has openly refused to license its tour guides—much to the chagrin of fellow Segway tour operators and many members of the Guild of Professional Tour Guides of Washington D.C. In the eyes of District regulators, the company’s guides are breaking the law; in the eyes of many Guild members, Segs in the City is violating something much more sacred, a standard of professionalism in a profession they take most seriously.

But passion is equally strong on the side of Segs in the City, which has invoked the Constitution and engaged in a legal battle to ensure its right to lead Midwestern tourists around on goofy machines without the permission of the government or a $200 slip of paper. The company’s owners, Bill Main and Tonia Edwards, are suing the city to free their guides from licensing requirements on the grounds that the system impinges on their right to free speech.

In any other town, such a lawsuit might be greeted with a shrug, or maybe a chuckle. (Indeed, Segs in the City’s attorney, Robert McNamara, filed an identical suit in Philadelphia after the city began requiring guides to be licensed in 2008. Eventually the suit was dismissed, with more of a whimper than a bang, after Philadelphia determined it couldn’t afford to issue the licensing exam.) But this is Washington, where even a minor regulatory matter can become grounds for a major First Amendment throwdown. Toss in a libertarian law firm, an Australian tour operation owner, and a multibillion industry, and suddenly Segways lie at the heart of a fight for freedom.

Photograph by Darrow Montgomery

Tourism in D.C. is serious business. In 2012, more than 18.9 million domestic and international visitors descended on the District to enjoy historical sites, visit free air-conditioned museums, and stand on the left side of Metro escalators. Of those millions, an untold number participate in the city’s plethora of tours under the guidance of men and women who are legally required to hold a District-issued license, making D.C. one of a handful of U.S. cities with similar rules, including New York, New Orleans, and Charleston, S.C. In 2012 alone, 423 new licenses were issued here. In 2011, it was 659.

The industry has been regulated since 1904, when Congress decided that those wishing to give a tour for profit must be licensed to protect out-of-towners from guides of ill repute. For decades, requirements to be a tour guide in D.C. ranged from the reasonable (background checks) to the ridiculous (guides had to have a doctor’s note testifying that they were not drunkards and did not suffer from vertigo).

“The old regulations used to be just completely outdated,” says Helder Gil, legislation and public affairs officer at D.C.’s Department of Commerce and Regulatory Affairs, which issues the tour licenses. “You had to be a U.S. citizen. You had to bring in six or seven letters of reference…We looked at some of these things and said this is just insane.”

In 2010, DCRA overhauled its licensing process. The old test, which included questions that had either more than one correct answer or no right answer at all, had been photocopied so many times that some of the images a guide had to identify were indiscernible. A new test was written that included more contemporary information.

DCRA worked with the Guild and tour operators to revamp the licensing requirements. “We want to make life as easy as possible for the guides who work here,” Gil says.

Changing regulations aren’t the only evolution in the D.C. tour industry. Guides are constantly monitoring city and cultural developments to keep their tours current, and new types of tours sprout up each year.

“You have to stay abreast of movies, especially with the kids,” says Tim Krepp, who has given tours in D.C. for seven years. The reflecting pool on the National Mall, for instance, used to be a touchstone for Forrest Gump references. “Now I’m getting a lot of, ‘Is this where the octopus was in Night at the Museum?’” Georgetown Cupcake is now a regular stop on his tours of Georgetown, though Krepp has never seen the eponymous TV show and isn’t quite certain why it appeals to so many of his customers.

Different attractions and administrations bring different waves of tourist groups, Krepp says, including many more groups of senior citizens after the completion of the World War II Memorial and a dramatic increase in schools from the inner city of Chicago when President Barack Obama was elected. A wave of interest in U Street NW has inspired tours of the neighborhood, which previously was far less visited than Capitol Hill or Georgetown.

Endless specialized tours have popped up in recent years to supplement the spring’s steady supply of eighth graders: tours focused on a specific era (the Civil War is popular, especially around its recent sesquicentennial); tours emphasizing certain heritages or identities (African American, Jewish, and LGBT tours are all available); and themed tours (including chocolate, spies, scandals, first ladies, cemeteries, and ghosts).

And, of course, the now ubiquitous Segway tours.

Segs in the City was the first to arrive in D.C. In 2003, Bill Main and his wife Tonia Edwards were running a bicycle rental and Internet cafe in Annapolis but didn’t see the cafe surviving with the increasing availability of wireless. “We were looking for some other opportunity,” says Main. “We came upon Segways.”

The Segway, a battery-powered electric vehicle that moves according to the way the rider shifts his or her weight, was introduced to the public to, in retrospect, outlandish fanfare in 2001. Before its launch, Apple co-founder Steve Jobs was quoted as saying the device would be “as big a deal as the PC.” Turns out that the Segway was not, as venture capitalist John Doerr predicted, bigger than the Internet.

This machine that was going to change everything has more or less become an easy punchline. After a period of media fawning, the Segway now mostly makes the news for being associated with doofuses or doofussy behavior. President George W. Bush, an otherwise athletic man, took a tumble off a Segway in 2003; Justin Bieber, who has of late become synonymous with the ridiculous, likes to ride one.

But Main and Edwards correctly predicted that in tourism, the Segway would find a natural home. According to Segway Inc., close to 1,000 Segway tour operations exist worldwide, including one at Disney, which initially used Segways to help employees get around but quickly saw the opportunity to use them as a tour mechanism. The couple became Segway dealers and launched tours out of Annapolis. They began giving tours in D.C. in 2004.

Main says the company started with three tours a day and soon expanded to five. He says he had no idea that a tour guide had to be licensed in D.C. until the Guild brought it to its attention in 2009. (Several guides interviewed for this story called the tour community “self-policing”; indeed DCRA has only one record of a citation issued for operating without a tour-guide license, and that was in 2007.)

“These folks kept saying, ‘You have to be licensed,’” Main says. “We had to look up the regulations and found there was indeed a licensing process involved.”

Main didn’t like what he saw, particularly the requirement (now defunct) that a guide had to be a U.S. citizen.

“I’m from Australia,” he bristles. “It’s quite discriminatory.”

Main had been already running a successful tour operation out of D.C., and he had to decide if he would require or pay for the $200 licenses for the dozen or so guides he employs at any given time, most of whom were local college students hired seasonally, in accordance with the regulations.

“We just ignored them,” he says.

Tamara Belden, president of the Guild of Professional Tour Guides of Washington D.C., strikes a civil tone when discussing the necessity of licensing and the lawsuit that has shaken up the tour-guide community.

Those wishing to lead tours as a licensed D.C. guide must first pass the District of Columbia Sightseeing Tour Guide Professional Licensing Examination. Applicants must successfully answer 70 of 100 multiple-choice questions, which are taken from categories including architecture, dates, historical events, gardens, museums, presidents, and universities. Do you have what it takes to lead around a group of sweaty tourists? Test your knowledge with these sample test questions, provided by DCRA. (mouseover for answers) Where’s John Philip Sousa buried? Answer: Congressional Cemetery What is the height of the Washington Monument? Answer: 555 ft., or 169 m. What was the name of the first substantial public school building in the city and where was it located? Answer: Wallach School located at 7th and Pennsylvania Ave SE. Sumner School located at 17th and M St NW is named after? Answer: Charles Sumner a Massachusetts Senator who attempted to ban segregated schools and public facilities in the city.

“The Guild is not a part of this lawsuit,” Belden says, “but we do support some baseline of licensing for ours and almost any profession.”

Belden doesn’t believe that passing the licensing test makes a tour guide a great one. “You need to study and research on your own to become the best you can possibly be,” says Belden, a retired Library of Congress employee who happened to be reading a book on the history of Union Station when I called her.

Her colleagues at the Guild were not quite as diplomatic on the matter of the lawsuit, licensing, or Segways.

“I think not only should there be licensing,” says John Ciccone, a Guild member, “but it should be far more stringent and demanding than it is.” He calls Segs in the City’s desire to forgo the licensing test “preposterous.”

“I think it’s a good idea for guides in our nation’s capital to have some standard of knowledge and skill,” Ciccone says. “It’s a way we project ourselves.”

Frank Fitch, another Guild member who has been giving tours for 16 years, objects not only to guides going unlicensed, but to the very notion of Segway tours. He claims to see two riders a week fall off the machines.

“It’s always a woman,” Fitch says. “I’m perfectly fine with women, but they don’t belong on Segways. I think it’s the center of gravity.” (Several guides also suggest that they regularly see serious accidents, but a public records request for Segway accidents that generated a police report in the past year yielded just three incidents, two in which Segways struck cars while turning left and one in which a Segway ran off the road on Barry Place NW.)

Beyond the Segway’s danger to the fairer sex, in Fitch’s mind, Segway tours post a threat to the quality of tour-guiding in town.

“They are never accurate,” Fitch says of Segway tour guides, echoing numerous Guild members who tell similar stories. He says he’s often leading a tour in front of the White House when a Segway tour rolls up. “They’re very general, and of course the people have questions, and these tour guides just do not know anything,” he says.

“And these are things covered on the D.C. test,” he adds. “What’s the building next to the White House? That’s the Old Executive Building.”

“The Segway people didn’t know anything about it,” Fitch says. “I’m appalled at what people are not told. It’s because they haven’t been trained.”

Not all Segway tours should be lumped together, of course. Half a dozen tour companies operate Segway tours in the District, and most of them require their guides to be licensed.

Segway Inc., which partnered with the Smithsonian to run Smithsonian Tours by Segway, isn’t pleased to see another Segway tour operator going rogue.

“It did come to our attention that that particular tour operator had sued the city,” says Gerri Moriarty, Segway’s director for U.S. sales. “[Main] made a big issue out of it. We felt it was imperative when we down [to D.C.] to make sure we did everything the right way.”

“We understand and support the District’s position on that,” Moriarty says of the regulation. “We’ve taken a liking to the licensing process…it ensures a certain level of minimum quality.”

Despite the passionate insistence by some that the licensing test is necessary, even too easy, not every licensed tour guide feels that way.

“I’m pretty agnostic on the usefulness of the license,” says Krepp. “The regulation should be there to protect the consumer, and I’m not sure how it does that.” Krepp, in agreement with several guides interviewed, thinks a more useful license might be one that required knowledge of the District’s traffic patterns.

“It would be much, much more about bus routing,” he says. “That’s the hard part. Knowing you can’t make a left turn on 17th Street during rush hour from Constitution.”

Main, unsurprisingly, feels there is no point to requiring the “baseline of knowledge” that the Guild supports.

“No point at all,” he says. “The test does nothing for our tour. What we do, and what we say—the test does nothing about it.”

Segs in the City guides follow a script, Main explains, with a little room for the personality of the guide.

“We’re not talking about the White House or the Capitol,” he says of the test material. “We’re talking about some obscure building. What sort of questions can they ask on a test that we don’t already know?”

Segs in the City generally has 12 to 14 guides working at a time, almost all undergraduate or graduate students, and Main says there is little retention from one summer to another. Paying $200 for each college kid who comes on board for a summer and never returns isn’t a great prospect for the company, financially. Though several Segway tour operators in the city say they pay for their guides to become licensed, Main points out he is not required to do so.

“Theoretically, it’s up to the individual to have the license when they apply for the job,” Main says. “I, the manager, don’t have to have a license. I just have to employ a person who does.” But, as Main maintains, “This is an argument of principle, not of economics.” He simply objects to the notion that a person should have to be licensed to speak on the history of the city, no matter who’s forking over the fee.

“People have written books about history with questionable facts in them,” he says. “I can say whatever I like in a prerecorded message [and play it for a tour].” So why require a license to speak to tour groups? “I said, ‘What’s the point?’”

Indeed, whether or not the Guild members’ accounts of hearing erroneous information on tours is true, there is no obvious evidence that holding a license makes someone a good tour guide or that not holding one makes someone bad. By the admission of numerous Guild members, the test isn’t even very difficult—so passing it is hardly evidence of prodigious knowledge. The main benefit to being a licensed tour guide might be access to the Guild (which only admits licensed guides, who must also pass written and oral exams and pay a $100 membership fee). Through the Guild comes access to the lucrative step-on guide jobs: hopping on motorcoaches bearing large tour groups and providing narration. But that particular feature benefits the guide more than the tourists.

Beyond the felony background check required of licensed guides, which could prevent the unlikely scenario that a con man would lead a bus of eighth graders astray and then rob them of their spending money, it’s arguable that the licensing process doesn’t do much to guarantee a quality tour. It’s also arguable that a visitor to D.C. who engages in a three-hour walking tour of the city’s cemeteries has a different aim than one who pays for a one-hour Segway tour of the Mall. For a visitor who’s been trudging from one monument to another in 90 degree heat for three days, vast quantities of rigorously examined and city-certified information might take a backseat to the novelty of riding upright on that two-wheeled machine that the mall cops have back home.

Photograph by Darrow Montgomery

Whether passing a test makes you a good tour guide is one matter. Whether the city should be able to regulate the industry is another.

At the heart of the Segs in the City lawsuit is principle. The company isn’t suing to avoid punishment for employing unlicensed guides—in fact, it was never punished. DCRA was unable to say if it was even aware that Segs in the City was doing so before the lawsuit was first filed in 2010. For the company, it was about liberty.

Robert McNamara at the libertarian Institute for Justice was the obvious choice to take the case, having already tried the similar one in Philadelphia. (The Institute, which is supported by donations, works pro bono.)

“I’ve never done a Segway tour,” McNamara admits. “My interest is in the First Amendment.”

McNamara argued for the court that the freedom of speech should protect guides’ right to communicate for a living. “There’s simply no good constitutional reason to require you to get a license before you can describe something for money,” he says. “It puts the government in the position of deciding who is sufficiently [qualified].”

A judge disagreed. After 18 months, the U.S. District Court issued a summary judgment in favor of D.C. Main and Edwards promptly appealed. The appeal is pending.

“All the facts are already in the record,” McNamara says. “We are appealing on the grounds strictly that he got the law wrong. He thought it was a regulation of conduct, not a regulation of speech.”

Gil of DCRA disagrees. “No, we are not trying to regulate what they say,” he says. “We’re trying to regulate a business, which it is.” Gil adds that DCRA held a comment period when overhauling its tour-guide regulations, and that Segs in the City did not participate.

McNamara sighs when asked about the comment period. “That’s been the DCRA’s line of attack against me,” he says. “It’s not my job to call the Constitution to their attention. You should really look to the Constitution.”

McNamara also calls the test a “somewhat random collection of historical facts” that don’t necessarily add up to much, particularly for someone who wants to give a tour on something like ghost history.

“I don’t think this is a controversial statement,” he says. “Ghosts aren’t real.”

A group of half a dozen folks in helmets stand in the hot mid-afternoon sun outside the Museum of American History. They’re watching a cheesy video as part of the hour-long safety training at Smithsonian Tours by Segway while the guide, Rick Tyson, a surfer-academic type, gets everyone’s paperwork in order. Then it’s onto the Segways, one at a time, as Tyson gives an individual lesson to everyone.

Smithsonian gardeners ignore the riders as they test out their new Segway skills in a courtyard. Tyson puts everyone through a few tests: weaving in and out of cones, coming to a quick stop, moving backward. (The difference between this and the eight-minute training session before a Segs in the City tour feels less like a difference between a company that licenses and one that doesn’t and more like the difference between a company that is run by very serious people who work for a federal government agency and one that named their operation after an HBO show.)

Out on the Mall, Tyson provides lively commentary that focuses, unsurprisingly, on the Smithsonians and their treasures. Some facts overlap with the Segs in the City tour, though Tyson seems to understand that to his customers, the Segway is more interesting than his commentary. Accordingly, he stops talking in front of the Capitol so people can take photos of themselves on the machines and spin themselves silly.