Inside Provincetown's Legacy of Transgender Representation

by Matthew Wexler

EDGE Media Network Contributor

Saturday July 10, 2021
Originally published on June 30, 2021

There's no denying that when the ferry glides into Provincetown Harbor, those on board feel a shift in the air. The picturesque peninsula on Cape Cod's northern tip has long attracted those seeking freedom and a place for self-expression.

From the Portuguese immigrants of the 1860s and the varied artists of the 1900s to today's flourishing LGBTQ community, Provincetown continues to be a haven of acceptance. Among those narratives, Fantasia Fair — newly rebranded as Fan Fair — is one of the most compelling: a 46-year-old legacy that empowers transgender and gender-fluid attendees.

Founded in 1975 by Boston's Cherrystones support group, the first Fan Fair welcomed 40 participants to Provincetown, a location chosen due to its LGBTQ inclusivity as well as its isolation for those looking for a haven to explore their gender identity. Held mid-October after the height of the tourist season, Fan Fair was the first of its kind, offering workshops, social activities, and medical, professional and relationship resources long before the term transgender was even part of the common vernacular. (This year's Fan Fair will be held Oct. 17-24.)

The Cherrystones recognized what visitors and locals alike have embraced for decades: Provincetown is a place to just "be." Regardless of what themed activities one might encounter, the destination's beauty is not solely sunsets and sandy beaches but the co-existence and intermingling of all facets of our LGBTQ community and allies. It's what keeps bringing Fan Fair director Dee LaValle back year after year.

LaValle began her transition nearly six years ago. Married with two children and a spouse and career she loved, LaValle nevertheless felt her life was crumbling. A friend suggested attending Fan Fair. "I started to feel my heartbeat," says LaValle of that first visit. "When I left, I cried like a baby because it was finally revealed what my truth was."

On the brink of divorce, LaValle asked her wife to come — spouses and partners are a crucial and welcome part of the Fan Fair experience — and she, too, "fell in love with the place," says LaValle. "Provincetown has a way of taking the noise out of your life."

LaValle says Fan Fair facilitates the opportunity to enter a community in safety, look in the mirror, wake up every morning and ask oneself, "Is this who I want to be? Is this who I am?" Provincetown, which she refers to as "the training wheels of life," becomes the backdrop for these life-changing experiences, and not just in workshops or other insular environments. Local hotels, restaurants and businesses have long embraced the annual event and see the transgender community as a vital part of the town's identity any time of year.

LaValle recognizes the shifting attitudes toward the LGBTQ community and strongly feels that despite broader transgender representation in the media, Fan Fair remains a vital resource.

"I've had a career and am moving forward with my journey, but I don't think for a second that kids have it any easier," says LaValle. "We still see those backdoor micro-aggressions that keep them from finding jobs. And everyone wants to fight for trans kids, but how will they succeed in life without the Equality Act? A 15-year-old kid who's not allowed to play on a sports team loses out on developing social skills. It's not just the sport, but finding friendship and community."

The Importance of Community

Fan Fair offers scholarships for those who would otherwise be unable to attend. Nationally recognized motivational speaker and Director of Health Care Advocates International's Youth and Family Program Tony Ferraiolo was once a recipient.

"Before I transitioned, I identified as a lesbian and went to Women's Week," recalls Ferraiolo. "I didn't know I was trans; there was no language around it, and it still wasn't safe to be out back then. But, going to Provincetown, I felt accepted. Like I belonged."

Ferraiolo had been working as a club promoter, and when he began to question his assigned gender, he discovered unexpected pushback.

"Here's the truth, a lot of my old community would say, 'We don't want anyone putting us in boxes,' and yet there was a wedge between the LGB and the T because some people didn't understand. Now, as an international trainer, I say, 'When you try to understand something you are not, it blocks you from acceptance.' Everyone struggles with something. Try not to hold people to your own agenda."

Ferraiolo remembers driving into town on a Sunday morning, ironically, as Women's Week was coming to an end. He had an anxiety attack and stopped in the parking lot on MacMillan Pier. "I had never met other trans people," says Ferraiolo. "But then I walked into register for the week and never felt more welcome in a community than when I stepped into that room. It wasn't just Fan Fair — it was the restaurants and shops, too. I even got a massage and felt very safe."

Provincetown is often described as magical, but the people are as memorable as the place. Vacationers return because of the warmth and hospitality of its residents and the business owners who see value in every human experience. That kind of energy is irreplaceable, and in many ways, infuses the Fan Fair experience.

Over the years, Ferraiolo has returned to Fan Fair as both a participant and a presenter, last time facilitating a panel of teens to tell their stories and hold a place of gratitude for those pioneers who paved the way. This October, he flips the script, engaging the older trans community to help affirm and empower the next generation.

"The newcomer is near and dear to me," says LaValle of the importance of Fan Fair intergenerational programming. "What would have happened to us if this didn't exist? Fan Fair has changed peoples' lives forever, and it's impossible to duplicate because it's all based on the safety of the town that completely accepts us."

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Matthew Wexler is EDGE's Senior Editor, Features & Branded Content. More of his writing can be found at Follow him on Twitter and Instagram at @wexlerwrites.