The 5 best cities and parades to celebrate Pride Month

Published June 2022

June is here, and with it, the colorful parades, demonstrations, and festivals that make up Pride Month. This month-long celebration recognizes year-round activism and is a call for greater unity, visibility, and equality for the LGBTQ+ community. From Key West’s famous drag shows to the street parades of New Orleans, there are Pride celebrations for community members and allies alike that take place all over the country.

Celebrations can last from a few days up to a full week, with some carrying all the way through the end of summer. Whether you’re looking for family-friendly festivals or the more risqué cabaret and comedy shows, we’ve rounded up our five picks for the best cities and festivals to celebrate Pride Month.

1. Portland, Oregon

With the weather warming up to near-perfect temperatures in the Rose City, Portland Pride Waterfront Festival & Parade, running June 12–19, has become the unofficial kickoff to summer and one of the largest donation-based Pride festivals in the U.S.

Festive parades, film screenings, art exhibits, and more provide plenty to do during the day. After-hours, Portland Pride is also a night owl’s dream, filled with comedy shows, themed DJ nights, and dance parties that go til dawn. Make sure to visit the oldest continuously-running cabaret in the country, the Darcelle XV Showplace. Here, 91-year-old Darcelle XV, the Guinness World Record-holder for oldest working drag queen, still performs six nights a week.

2. Key West, Florida

With its official philosophy of “One Human Family,” it’s no surprise the tiny sun-drenched island of Key West has become legendary for its year-round openness and eccentric, laid-back style. Key West can be considered an international mecca for the LGBTQ+ community; the U.S.'s first openly gay mayor was elected here, and the island is home to the first-of-its-kind Key West AIDS Memorial.

June is when the small town really comes alive for its Pride Month celebrations. From June 1–5, the Pride calendar is packed with talent shows, pool parties, street fairs, drag shows, Pride bingo, and, of course, the annual Key West Pride Parade—of which Vacasa is a proud sponsor. And while you’re strolling Key West’s historic streets between events, strike a pose in front of the city’s four rainbow crosswalks!

3. San Diego, California

Can't make it out to celebrate Pride in June? Lucky for you, one of the largest Pride events in the country takes place in sunny San Diego July 9–17.

San Diego Pride is back in-person this year at the famous Balboa Park and plans to live up to this year’s theme of “Justice with Joy” with a whopping 200 floats, performances by 170 diverse artists and activists, educational and art exhibits, and more. And for those looking to break a sweat while supporting diversity, pack your wackiest rainbow running gear and sign up for San Diego’s Front Runners Pride 5K, which donates all proceeds to the week’s charity partners.

4. Provincetown, Massachusetts

Don’t be fooled by this quaint New England coastal town nestled at the tip of Cape Cod. Provincetown is all things glitter and magic, with a thriving artist colony that embraces outsiders and free self-expression. And visiting P-town during its Pride Weekend (June 3–5) is one of the best ways to celebrate.

Take a ferry or shuttle from Boston and arrive just in time to take in some of the town’s history via guided trolly tour, where you can stop for a drink at the oldest gay bar in the U.S. Once you’ve got your bearings, head over to Town Hall for a comedy showcase featuring queer stand-up comics from all over the country.

5. New Orleans, Louisiana

When a town is as world-famous for its street parades as New Orleans, it's no surprise this city goes all out for its Pride festivities. After all, New Orleans was once voted the second most-welcoming city for LGBT people in America. The Big Easy officially hosts Louisiana’s largest LGBTQ+ parade as part of its Pride Weekend taking place June 9–12, with more events happening all month long, including Black Pride NOLA.

Though NOLA parades are famous for their flamboyant costumes and more, ehem, mature audiences, make sure to bring your little ones along to “Family Equality Day.” Here, families of all ages gather to celebrate with drag queen story time, fan decorating workshops, and even a children’s march for our youngest of activists.

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