Orlando's LGBTQ+ Weekend marks 35 years of magic

Orlando’s big LGBTQ+ weekend has celebrated the city’s community for 35 years. From red shirts to pool parties to drag pageants, the idea has always been to be visible and proud.

What started out as Gay Day at Disney’s Magic Kingdom has now expanded to a weekend of events with various organizations. With groups like GayDays, Girls in Wonderland, KindRED Pride Foundation and One Magical Weekend, there is something for everybody.

The weekend’s origins trace back to Gay Day at Magic Kingdom, which first took place on June 1, 1991 in front of Cinderella’s Castle before the park’s parade. The idea was for the LGBTQ+ community to gather and be seen — at the most Magical Place on Earth — when doing so could be dangerous. 35 years later, Gay Day at the Magic Kingdom falls on June 6 and a group photo is expected to take place at 5 p.m. in front of the castle.

Gay Day at Magic Kingdom is a community led, unofficial event in which attendees are encouraged to attend and wear red. It’s a nod to red in the Pride flag representing life; original organizers chose this color to recognize other “kindred spirits” at that first gathering, according to KindRED Pride Foundation.

There will also be a variety of meet ups happening that same Saturday such as leather men meetup, trans meetup and lesbian meetup. More information on the times and location are available on GayDays.com, shared by the organization Gay Days, Inc.

Celebrating 35 years, GayDays will take place June 4-7 at Holiday Inn & Suites Orlando SW.

Gay Days, Inc., which organizes this specific set of LGBTQ+ events, originally announced a 2026 “pause” Feb. 8. They reversed course Feb. 24, advising they were moving forward with a renewed format designed to create a more immersive, community-centered experience, including exclusive use of the host hotel.

“We didn’t want to move forward unless we could deliver the experience our community expects,” said Charles Cantrell, co-owner and event partner. “Now that everything is in place, our focus is on bringing people together and making 2026 a strong return.”

For 2026, the entire property, including all guest rooms, event spaces and amenities, will be reserved exclusively for GayDays attendees. The goal is to provide a private, welcoming environment where the LGBTQ+ community can gather, celebrate and connect throughout the weekend.

“We’re trying to get back to our roots,” shares Josh Duke, co-owner of GayDays. “We did an entire hotel buyout. So all of the events are on site… The hotel has gone above and beyond. They created a special menu for us, special drinks and special drink pricing. We have a VIP experience for the first time this year that we’ve introduced.”

He says there were a lot of positive changes made and it was all because of feedback that GayDays received over the last couple years from guests. He hopes this year will show that they are listening and want to live up to the community’s expectations.

The earlier planning pause allowed organizers to evaluate options and secure a structure that supports both the guest experience and the long-term stability of the event, they say.

The official programming will include daytime pool parties, nightly entertainment, the GayDays Vendor Expo and marketplace, Mr. GayDays and Miss GayDays Pageants, the Red Room late-night experience and adult-themed programming. The event times will vary as June 4 has the opening party, June 5 has the Miss GayDays Pageants, June 6 will have Mr. GayDays and June 7 will close with a comedy show.

Duke says GayDays will cater to its audience as there is something for everybody, no matter the age. He wants guests to feel free to immerse themselves in the experience.

“I encourage people to come out and just be social, just be yourself,” Dukes says. “Our staff and volunteers are there to make sure that you’re having a good time. If you have a complaint or suggestion, anything, we encourage people to come up and talk to us.”

This year, the organization is introducing the GayDays Community Art Project to honor the 10-year remembrance of the Pulse tragedy. They invite every guest to bring a small red or rainbow-colored item — a pin, charm, bead, button, key or trinket.

Throughout the weekend, these pieces will come together to create a collaborative work of art built by the community. The completed artwork will be unveiled at the Sunday night closing party.

“We wanted to commemorate it with [the City of Orlando] tearing down the Pulse building this year [since] the city is going to be building a memorial,” Duke says. “We wanted to remember and honor that… We have a local artist who’s going to be on site building this out over the course of the weekend.”

Duke says the organization’s hope is that once the memorial is finished, they can donate it as a gift from GayDays. He notes that the community can’t forget to remember the fight that still continues in today’s political climate.
He is thankful to the Orlando community because of their longtime support as well.

“We encourage people to be out and proud,” Duke explains. “If we don’t fight for our rights, nobody else is going to. We don’t want this to be a political environment at GayDays as we want this to be a place where people can step away and be themselves and not have to worry about what’s going out on in the outside world, and that’s the environment that we try to create.”

GayDays is June 4-7 at Holiday Inn & Suites Orlando SW, located at 5711 W Irlo Bronson Memorial Hwy in Kissimmee. For tickets, events and more information, visit GayDays.com.

Celebrating 26 years, Girls in Wonderland will be held June 4-7 at SpringHill Suites by Marriott & TownePlace Suites.

Girls in Wonderland is an annual celebration hosted by the women-led company Pandora Events as a way for queer women from around the world to gather and party in celebration of Sapphic, or WLW (women loving women), Pride.

Yesi Leon and Amy Alonso co-founded Pandora Events and launched Girls in Wonderland in their early 20s.

According to Leon, the first Girls in Wonderland was hosted in Orlando in 2000 and around 800 guests from all around the country attended. Since its founding, Girls in Wonderland has been an inclusive festival where queer women from around the world can connect through a series of festivities.

Just last year, over 10,000 guests attended the festival with many staying in the Orlando area.

Alison Burgos, a partner behind Pandora Events, says Girls in Wonderland is a weekend for the LGBTQ+ community to come together in safe spaces to celebrate each other. She says that even though it’s catered toward queer women, men and allies are welcomed.

“I think we honestly create a place where everybody can feel safe and comfortable getting to know people, whether you’re solo or in a group or it’s the first time or 20th time,” Burgos shares. “I think that people who have been coming for years love that.”

As organizers, Burgos wants to see guests be their authentic selves. She gets emotional when she sees the impact Girls in Wonderland has; one of her favorite memories is when she proposed to her wife in 2012.

“I walked on stage at House of Blues and got on my knee and asked my wife to marry me,” she says. “That was also a huge personal highlight for us, and everybody cheered. All of our friends and family that were there, it was very special moment.”

The team is filming a documentary to share the story of Pandora Events and how Girls in Wonderland formed. Burgos says the event has always been an open door for the entire LGBTQ+ community.

“We were one of the first festivals that always tried to make sure we were trans welcoming, not just accepting,” Burgos explains. “I think that’s important right now where there’s so much divisiveness in trying to separate us, even in our LGBTQ community.”

Safety is a priority for the organizers as they have internal and external security companies, while also working with Orange County Police who will be present at events.

For the events, the opening party will be on June 4 and will feature performances from Les Vixens at Cuba Libre. The pool parties are all weekend and start June 5 at the host hotel. The comedy show will feature Sammy Ruddy, a comedian who has performed on “The Tonight Show with Jimmy Fallon” and “The Late Show with Stephen Colbert.” The show will be at Mangos at the side venue.

Themed parties will continue into the weekend such as sapphic safari and space cowgirls and aliens. To close out the fun, the last chance party will be at the host hotel.

“Every day there’s an opportunity to connect with other girls and make friends or maybe even have a love match,” Burgos says. “Its ways for us to be connected and present and create like that safe space for each other. We want people to have a great time and enjoy great music and great shows but also being connected to your community and making friends or having fun with the friends that you’ve already made.”

For Burgos, she knows Girls in Wonderland creates memories for guests that will last a lifetime. She says it feels great to be part of something bigger than yourself that touches others in special ways.

Girls in Wonderland is June 4-7 at SpringHill Suites by Marriott & TownePlace Suites, located at 13295 Hartzog Rd. in Winter Garden. For tickets, events and more information, visit GirlsinWonderland.com.

The Pride Cup, presented by the KindRED Pride Foundation, is proudly returning June 5–7 to bring together LGBTQ+ athletes, sports fans and community allies.

The Pride Cup is billed as one of the most inclusive and high-energy sports weekends in the country. The community experience is a multi-sport competition. The 2026 edition will feature tournaments and competitions across basketball, volleyball, pickleball, kickball, cornhole, golf, rugby and the Rainbow Run 4.9K.

Athletes of all skill levels are invited to compete in an environment centered on inclusion, diversity, friendship and pride. The tournaments will provide opportunities for attendees to meet LGBTQ+ locals and players from all over the country.

“This event is about far more than competition,” organizers have shared. “It’s about creating visibility, building community and celebrating Pride Month through sports, entertainment and connection. Orlando becomes the center of the LGBTQ+ universe that weekend, and The Pride Cup adds an incredible daytime sports and social experience to the energy of Gay Disney Weekend.”

The KindRED Pride Foundation was inspired by the desire to expand the magic created by the 35-year tradition of the original “Gay Day at Magic Kingdom” in Orlando.

Its mission is to honor the kindred spirit, bravery and courage of the original attendees back in 1991. It wanted to expand on the “grass roots” desire to bring the community together to celebrate their differences. Like-minded charities within the LGBTQ+ community support its endeavors by producing sporting, music and other special events.

For the sport this year, the basketball tournament will be two days with Round Robin played on June 6 and then single elimination playoff games on June 7.

A new cornhole tournament will also be introduced this year. In the two-day tournament on June 6-7 teams will be placed in round robins by blind draw, as organizers want teams from around the country to play against other, unfamiliar teams.

The Pride Cup also announced it partnered with Bowled Over Promotions to host a one-day golf outing for the benefit of The Pride Chamber. It will be a game of 18 holes, starting at 8 a.m. on June 5.

The kickball tournament will be June 6-7. Last year, the tournament was composed of more than 20 teams from all of the major Florida LGBTQ+ Kickball leagues including OUT Orlando, OUT Tampa, Rainbow Sports League in Fort Lauderdale, Stonewall Gainesville, Stonewall Jacksonville and more.

In Pickleball there will now be the addition of a team Minor League Pickleball event where teams of four compete against each other. This will also be June 6-7.

The Pride Cup is also a part of the 10th Annual Rainbow Run/Walk. In memory of the 49 lives lost at Pulse, the Rainbow Run is a 4.9K virtual experience that you can do from anywhere in the world. The virtual run can be done at any location at the runner’s pace.

Held in partnership with The Pride Cup, Scrum In The Sun is an inclusive rugby tournament hosted by the Orlando Otters RFC, Central Florida’s first inclusive rugby club. The tournament is on June 6 and is an inaugural event that brings together athletes and allies from across the country.

This year the soccer tournament also take place June 6. Teams must play a minimum of three games.

For volleyball, there is a 6v6 recreational grass volleyball tournament and a 4v4 grass volleyball tournament. The number of days and format for the tournament will change depending on the number of teams that participate.

Beyond the sports, The Pride Cup weekend is designed to connect athletes directly into the larger weekend experience through partnerships with Orlando’s most recognized LGBTQ+ event brands.

Hyatt Place Orlando/Lake Buena Vista is the official host hotel of the Pride Cup. The Hyatt Place is also home to the Pride Cup Opening Party on June 5 and Chill Zone Pool Parties on June 6-7. All sports will be played less than two miles away from the host hotel at Lake Buena Vista High School.

The Pride Cup, presented by the Kindred Pride Foundation, is June 5-7 at various locations in Central Florida. Go to KindredPride.org/Pride-Cup for more information.

One Magical Weekend and Bear Jamboree will return June 4-8 with a weekend filled with entertainment, pool parties and community.

With 11 parties — ranging from sunlit pool parties to late-night after-hours — every event is designed to keep the magic going.

One Magical Weekend began as a Florida Pride-side celebration at Walt Disney World and has grown into a multi-day offering of LGBTQ+ events. Held during the first weekend of June each year, it brings together thousands of guests from around the world at the Sheraton Orlando Lake Buena Vista Resort. What started as a celebration of pride has evolved into a beloved tradition that continues to expand with DJ lineups and immersive entertainment.

Last year, Pineapple Healthcare owners Ethan and Erick Suarez purchased the event organization from co-founders Tom Christ and Billy Looper. Suarez says the organization has been very blessed and is a very safe and welcoming space.

“I’ve had friends that I’ve been in touch with for five to 10 years now that I met at One Magical Weekend,” Suarez notes.
He says even if guests come solo, the welcoming environment will allow them to make new friends that will last a lifetime. He notes that guests should always be themselves.

One Magical Weekend’s “sister” event Bear Jamboree was created to celebrate the bear community and their admirers with an inclusive, high-energy LGBTQ+ experience. It launched in 2023 and is held at the Crowne Plaza Lake Buena Vista, the official Bear Host Hotel.

When it comes to One Magical Weekend’s events, Suarez says the community is like a family. He invites guests to go back and forth between One Magical Weekend and Bear Jamboree.

The One Magical Weekend welcome party kicks off on June 4 with DJ Kitty Glitter. The pool parties will be June 5-7 starting at noon until 6 p.m. In previous years, thousands have attended to soak up the sun. This year there will be six DJs.
Riptide at Disney’s Typhoon Lagoon is known as the ultimate private party. The waterpark turns into a personal paradise June 5 from 8 p.m.-2 a.m.

For a night of pure enchantment, the Red Party Ringmaster will be held at the House of Blues in Disney Springs on June 6. Want to dress up? Attend “A Night of 1,000 Ariana Grandes,” a singalong to all of the pop star’s albums at the host hotel. Wigs are encouraged.

To close out the weekend, there will be a drag brunch from 10 a.m.-1 p.m. at Zest Bar and Grill, located in the host hotel. It will be hosted by Daisy Dior and will include performances from Onix Mendoza, Jade Essence Hall, Michelle Du’ Soleil and Eureka O’Hara.

Bear Jamboree’s pool parties will be held June 5-7. From June 6-7 there will be Bearaoke, Bingo and dance parties. For laughs, Jessica Kirson, a lesbian comedian, will perform on June 6 at 8 p.m. in the Hyatt Place Orlando.
Suarez says Riptide is the pinnacle world class experience for him.

“What other time can you say that you’ve gone to a Disney park and there are no kids around?” he explains. “It’s completely LGBTQ+ and you get to be a kid again. I love that.”

Suarez notes that the hotels for both events are set for the foreseeable future. He says this allows for stability in the organization. Planning events that are the size of One Magical Weekend and Bear Jamboree involve many sleepless nights, he adds, but says it’s worth it.

“I’ll go into an event, I’ll sit in the back and see the crowd, just authentically living their best life, and it brings joy to my heart … I know the rest of my production team feels the same way,” Suarez shares. “We have some long days, and we check into the hotel on the Monday before One Magical Weekend, so we’re there four days before to build the production.”

Suarez says there will be more information about the fine details on social media. He encourages people to follow the organization so they can have the best experience for the weekend.

One Magical Weekend and Bear Jamboree are June 4-8. One Magical Weekend will be at the Sheraton Orlando Lake Buena Vista Resort, located at 12205 S. Apopka Vineland Rd. in Orlando. Bear Jamboree will be at Crowne Plaza Lake Buena Vista, located at 8686 Palm Pkwy in Orlando. For tickets, events and more information, visit OneMagicalWeekend.com and BearJamboree.com.