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Fantasia Fair / Transgender Week (1999)

Fantasia Fair / Transgender Week (1999)

©1999, 2013 by Dallas Denny

Source: Denny, Dallas. (1999). Fantasia Fair/Transgender Week. Unpublished essay.

I wrote this at a time when the Board of Directors of Fantasia Fair was considering transitioning the event to a new format and a new name. In the end, it remained simply Fantasia Fair. I remain enthusiastic about the event.



Gentle Reader, I realize the following sounds like a paid advertisement for Fantasia Fair/Transgender Week, but I’m plugging the event on my own accord because it’s an event you need to know about.


Fantasia Fair/Transgender Week

By Dallas Denny


I have seen the future, and it is called Transgender Week.

For the past 24 years in the resort town of Provincetown on the very tip of Cape Cod there has been every October a wonderful, week-long transgender event. I’m talking, of course, about Fantasia Fair.

Those who have been to Fantasia Fair know it’s a full-immersion experience, with an entire trans-friendly town available for those experienced at crossdressing, but plenty of hand-holding for first-timers. There are workshops, seminars, luncheons, receptions, house parties, banquets, music, a first-class all-trans cabaret show, and a Fantasy Ball at which it is difficult to tell the townies from the FanFair participants. Those who’ve attended past Fairs know that unlike the typical transgender event based in a hotel in a big city, Fantasia Fair spills out into the streets of the ever-welcoming Provincetown, that gayest of gay resorts. There is an entire village to see and in which to be seen, and for an entire week transfolk are visible on every street, in every guest house, every boutique, every nightclub, and every restaurant.



Those who have attended Fantasia Fair and many who haven’t know that going to the Fair can cost several thousand dollars, what with airfare, registration and lodging (lodging for 8 nights is included with registration), and spending money. In fact, Fantasia Fair has gained a reputation as an event for wealthy, closeted crossdressers. That’s not true on any account. First, FanFair is not limited to crossdressers; in fact the Fair is a diverse event, with as many transgenderists and transsexuals as crossdressers. And few Fairgoers are closeted. Second, only a few of the attendees are wealthy. Most Fairgoers must make sacrifices in order to attend. The Fair may seem costly, but that’s because it lasts a week rather than two or three days and because lodging is included in the registration fee. Although the Fair does cost more in absolute terms, on a per diem basis it’s less expensive than the Be-All and only a few dollars more than Southern Comfort.

In recent years Fair organizers have worked especially hard to cut costs and give attendees a lot of bang for their buck. Registration includes a LOT of meals. For instance, there are at no extra charge two evening banquets, six luncheons, a welcome buffet and a goodbye brunch, a church supper, a wine and cheese reception, an Apres-Follies buffet. And of course there is a wide variety of workshops given by world-class professionals, as many as 16 per day. Fairgoers can learn to speak more femininely (or more masculinely), learn how to groom themselves, work on their interpersonal relationships, or immerse themselves in transgender history or political theory—in the course of a week there is plenty of time to do all these things.



At one time, our community divided itself into drag queens, crossdressers, and transsexuals. By those obsolete standards, the Fair, in early years, promoted itself as an event for crossdressers. But Provincetown is full of drag queens, many of whom participate in the Fair, and the Fair has always included transsexuals and people who would today identify as transgender. In fact, there’s a classic 1980 Playboy article in which author D. Keith Mano talks about romancing a transwoman who was clearly on hormones. Throughout the nineties, the Fair has become an increasingly more diverse event. There are lots of transsexuals; in fact, a first-timer at last year’s Fair told me she found a higher percentage of transsexuals at the Fair than at any other gender community event. There has been a sizeable contingent of gay crossdressers throughout the nineties, and the Fair has begun to aggressively recruit FTMs. There are also many people who occupy gender territory somewhere between the classic definitions of crossdresser and transsexual, i.e., transgenderists. In fact, many of the transsexuals and transgenderists at the Fair first came out in P’Town and through the years explored their identities.


But Again, I Say, Isn’t It Expensive?

There’s something about one big sum that puts people off. They don’t seem to mind spending money so long as it’s broken down into digestible lumps. Most folks would rather pay $300 for registration at a gender conference and $85 a night for four nights lodging than $580 for registration which includes the room, even though the latter represents a savings of $60.

Certainly, the check one must write for a week at Fantasia Fair is a sizeable one. Consequently, FanFair has always been a small event, with attendance most years between 125 and 150. But these numbers have grown during the nineties, thanks to new and innovative ways of registering. It’s possible to attend half the Fair, for instance, or even for a single day. So no, it’s not all that expensive to come to Fantasia Fair. And it’s about to get even cheaper.

Women’s Week

Provincetown is one of those burgs that has a population of 5000 in the winter and 80,000 in the summer. After the mid-September, tourism drops off and the town begins to roll up the sidewalks. At least, that’s what used to happen. The Provincetown Business Guild has worked hard to extend the season by offering reduced rates and sponsoring special events in late September and early October. Now the season extends through late October, with the last big event being Women’s Week, which brings some 6000 lesbians to town. Fantasia Fair, which is of course, a much smaller event, begins to gear up as Women’s Week is winding down—but of course 125 transpeople cannot match the spending power of 6000 women, no matter how many boutiques they hit. A few establishments, hoping to separate Fantasia Fair attendees from their money, stay open a few days after Women’s Week, but the town visibly shuts down throughout the Fair.

To attend Women’s Week one need only show up. There is no registration, no need to book a room or give anyone any money. For those who can fly, drive, take the bus, or walk to Provincetown, there are thousands of women with whom to socialize and dozens of events to attend: concerts, cabaret, comedy acts, workshops, plays, and a prom. Provincetown Reservations sells tickets to the non-free events; those without money are still able to participate in the many free events—and of course, can socialize with the other 5999 women. It’s a powerful experience to see Provincetown’s Commercial Street packed wall-to-wall with lesbians of every age, size, and social class, all having a good time.

If the Women’s Week formula works well—and it does, as can be attested to by the ever-increasing numbers of women in attendance—why couldn’t we do the same for transpeople?


Transgender Week

Fantasia Fair is too special an experience to be the sole property of the well-to-do. Throughout the nineties the organizers have worked hard to reduce the cost of the event, shortening it from 10 days to 7, bargaining hard with bed and breakfast owners and restaurant managers, shaving a dollar here and there from the cost. But there’s only so far one can go by such methods. Last year, the Board of Directors of the Outreach Institute, which is the organization which sponsors Fantasia Fair, came up with the novel idea of gradually transforming the Fair into Transgender Week, using Women’s Week as a model towards which to work.

The decision of the organizers to transform Fantasia Fair into Transgender Week was not uncontroversial. Some of the long-time attendees have been concerned that the specialness of Fantasia Fair will be lost—and let me assure you, Fantasia Fair is indeed a most special event. How will Transgender Week be able to sustain the maintain the Fair’s wonderful ambiance? How will frightened first-timers be made gently comfortable? How will the house system be kept alive—the house system being a group of like-minded transpeople who are rooms in the same bed and breakfast every year and throughout the week of Fantasia Fair form close, warm bonds.

Those who are concerned are right to be so. This year is a big risk for Fantasia Fair. There is much to lose—Fantasia Fair itself—but there is also much to gain—Transgender Week. It’s a risk, but the organizers are determined to go ahead. This year Fantasia Fair’s 25th, the Fair has begun its transformation into Transgender Week. This year we will see the last of the old Fantasia Fair and the birth of Transgender Week. It will be a nostalgic time, and a time of new hope.


So What Does This Have To Do With You?

So what does this have to do with you? It means that if you’ve always wanted to attend Fantasia Fair you had better get busy and get there, for this will be your last chance. And it also means that if you want to have a good time but don’t have the money to go to the Fair, you can come to Provincetown anyway. And it means that if you’ve ever wanted to play music, perform your play, give a lecture, or raise funds for your organization, you’re welcome to come to Provincetown during the Fair and do so. Where you crash and what you will eat and how you will find a venue and audience for your performance will be your own responsibility, but there will be plenty of opportunities for you. And as a bonus, you will be able to march in the world’s first-ever transgender pride parade. So c’mon to Provincetown this October. If you can’t come for Fantasia Fair, then come for Transgender Week.

For the dates and other information about Fantasia Fair, check out <>