Small Towns, Big Pride

These six destinations prove diversity and inclusion come in all sizes.

Matthew Wexler
Jun 24 · 7 min read
Aquatic parade participants at Provincetown Pride. Photo by Dan McKeon.

Rainbow flags are flying high in New York City, San Francisco, and countless other metropolitan hubs this month as the 50th anniversary of the Stonewall uprising nears, and WorldPride descends on the United States for the first time in its history. But big things also come in small packages. The following six destinations have their own legacies to share, spearheaded by local LGBTQ artists, activists, entrepreneurs, and allies marking a queer renaissance that shows no signs of slowing down. The best part? These communities’ celebrations happen throughout the year, so there’s still time to make plans for your own destination Pride party.

Provincetown, Massachusetts

Population 2,581

Tucked away on Cape Cod’s northern tip, Provincetown began promoting itself as a cultural escape after the Portland Gale of 1898 — a mega-storm that wiped out fishing villages along the East Coast. Artist colonies formed, including the Cape Cod School of Art in 1898 and the Provincetown Players in 1915. This wave of creative freedom also brought a sense of acceptance and community that still resonates.

A shell-inspired costume at Provincetown Pride. Photo by Dan McKeon.

“It’s such an interesting mix of people,” says Fred Latasa-Nicks, board president of the Provincetown Business Guild and owner of Strangers & Saints, a bustling Mediterranean restaurant named after passengers on the Mayflower. “No one is better or worse. We come together in a way that is genuine, standing up for who we are. Everyone has a voice here. I lived in the Castro for eight years and the West Village for 20 — neither of them felt like a community the way it does here.”

How to go: Provincetown’s population swells in the summer months, with benchmark events such as the epic Carnival Week (August 15–24), an LGBTQ cornucopia of parties, art fairs, and performances.

Asheville, North Carolina

Population 92,452

Okay, maybe Asheville’s more of a small city than town, but it still merits mention here because of its close-knit community vibe. George Vanderbilt fell in love with Asheville’s fresh air and mountain vistas, choosing to build his grand 250-room French Renaissance chateau, Biltmore House, on 8,000 acres. The estate has become the city’s benchmark attraction, but only scratches the surface of why Asheville appeals to LGBTQ travelers and residents.

Yvonne Cook-Riley, who can trace their family lineage back seven generations, says there’s a particular vortex and energy here that resonates with the LGBTQ community for a specific reason. Riley, a Vietnam veteran and board member at large for the Transgender American Veterans Association, says, “You will feel connected to the earth. When you walk the trails here, you’ll know the love and energy of the Blue Ridge Mountains. Many of us in the LGBTQ community feel oppression because of what’s happening in our country. We don’t give ourselves credit for our worthiness to represent the universe and the land.”

Blue Ridge Pride returns on September 28, but Riley acknowledges that pride and self-acceptance takes a lifetime. “It’s a personal journey here. It’s not something we can bottle like our beer. You have to be here to experience it.”

Key West, Florida

Population 24,565

It’s no wonder that one of the 20th century’s most prolific playwrights and gay legends, Tennessee Williams, found respite and creative inspiration at the southernmost point of the continental United States. It’s believed that the Pulitzer Prize-winning author completed A Streetcar Named Desire while staying on bustling Duval Street. More than 70 years later, Key West’s island vibe continues to resonate with LGBTQ travelers, who flock to the walkable island to enjoy not only the palm trees, sunsets, and water activities, but also its openness — in 1983 it became one of the first cities in the United States to elect a gay mayor.

Key West’s moniker, “One Human Family,” rings especially true with Key West Business Guild executive director Dan Skahen. “Same-sex couples feel comfortable holding hands down the middle of a busy street,” he says. “They can come here and have any public display of affection they like.” Hailing from a small Wisconsin town but a Key West resident for more than 25 years, Skahen stresses that “you tend to forget how the rest of the world treats LGTBQ people.”

A rainbow-flag run at Key West Pride. Photo courtesy of Florida Keys News Bureau.

Key West is primarily a coral island (read: no sandy, swim-friendly beaches), so renting a large house with a private pool has become increasingly popular. Skahen suggests hiring a private chef or chartering a yacht for a more luxurious experience, but the island’s many festivals, such as Tropical Heat (August 14–18) and Womenfest (September 4–8) offer plenty of opportunities to mingle with locals and other tourists.

Portland, Maine

Population 66,417

Maine’s recently revived moniker, “The Way Life Should Be,” rings true for longtime resident and innkeeper Dale Northrup. For more than 60 years, he’s witnessed Portlandians treat one another with the kind of dignity and respect that transcends sexual or gender identification. “Nothing is startling or remarkable about seeing someone from the LGBTQ community,” he says. “It’s a very comfortable place to live.”

So comfortable that Pride Portland!’s annual, community-driven parade has overflowed with church groups bearing signs such as “Sorry for all the hateful things done in the name of God” and bright yellow Portland public school buses packed with rainbow-clad students. This year’s grand marshals included Ian-Meredythe Lindsey, a trans activist involved in securing a nonbinary option added to Maine state IDs, and Dykes on Bikes, which has kicked off Pride parades since their 1976 San Francisco debut.

In 2012, Maine was one of the first states to legalize same-sex marriage by popular vote , proving there’s power in the people. Later this summer (August 12–16), EqualityMaine will host The New Leaders Summer Project in nearby Unity for LGBTQ teenagers to cultivate emerging voices in the ongoing fight for equality.

Palm Springs, California

Population 48,375

In its heyday, Palm Springs attracted entertainment industry heavy hitters seeking to avoid the paparazzi while remaining close enough to Los Angeles to honor their studio contracts. Among them were a host of closeted actors such as Cary Grant, Randolph Scott, and Rock Hudson.

The iconic palm trees provide the backdrop for the Palm Springs Pride Parade. Photo courtesy of Palm Springs Bureau of Tourism.

Restaurateur Dean Lavine of the Black Book Bar describes today’s Palm Springs as “the Castro of the Coachella Valley,” where travelers flock for upwards of 350 days of sunshine per year and a preserved microcosm of midcentury design that’s become as big of a draw as the San Bernardino Mountains.

Lavine has spearheaded the Arenas District, a nonprofit community effort to unite LGBTQ-owned businesses. “We’ve banded together to say, ‘Look at what we’ve got here.’ I’ve seen a lot of fracturing in our community,” he reflects. “But that doesn’t happen in Palm Springs. We’re blessed and should be giving back.” The consortium hopes to raise funds for local charities such as the Desert AIDS Project.

The San Bernardino Mountains frame the procession at Palm Springs Pride. Photo courtesy of Palm Springs Bureau of Tourism.

Palm Springs offers various queer-centric celebrations beyond the busy month of June, including Cinema Diverse: The Palm Springs LGBTQ Film Festival (September 19–22) and Greater Palm Springs Pride (November 1–3).

Saugatuck, Michigan

Population 960

While 1969 heralded the beginning of an era for LGBTQ rights, in Saugatuck it marked the end of one when the legendary gay bar, The Blue Tempo, burned down. The idyllic locale on Lake Michigan’s eastern shore had become a haven for queer travelers hailing from Detroit and Chicago. But Saugatuck quickly bounced back. Along with the town of Douglas across the Kalamazoo River, it has become a lakeside haven known as “the art coast of Michigan” for its longtime patronage of arts through the Ox-Bow arts residency program and a small but mighty epicenter for progressive thinkers and doers.

“I’ve seen a great shift,” says restaurateur Mindy Trafman, who bought a cottage 12 years ago and made Saugatuck her permanent home in 2014. It was after the passing earlier this year of Carl Jennings, a longtime community leader and LGBTQ advocate, that Trafman fully recognized the value of allies. “Out of his memorial came the idea to have a Pride event with speakers, and it was amazing to have the contributions of people who don’t identify as LGBTQ. Their support really made it happen.” Jennings’ legacy lives on through the work of West Shore AWARE, an organization “dedicated to increasing the positive influence and public awareness of the contribution that gay men and women make to the community in which they belong.” Its 16th annual White Party is on August 17.

About the author: Matthew Wexler is a nationally recognized lifestyle editor and writer whose work has appeared in more than 20 publications and online media outlets, including Hemispheres, Wine Enthusiast, and Passport. Matthew is a member of the New York Travel Writers Association and a recent Eugene O’Neill Theater Center’s National Critics Institute fellowship recipient.

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