EventsKey West Bear Weekend

Do you think you have what it takes to be the next Mr. Key West Bear?

Key West Bear Weekend is BACK, and the dates are set for NOVEMBER!

After two years of pandemic cancellations, Shane Tate Presents Key West Bear Weekend, returns in 2022! The very popular and VERY HOT Bear weekend, sponsored by and Bear World Magazine, will be held from November 2nd to November 6th, and will be a perfect way to heat up your late autumn! 

Join the Bears in the hottest location in Florida for some fun and frolics in the sun! This year’s events will include tons of pool parties and happy hours, along with the Britney Vs. Madonna Dance Party, the Fuzzy Flamingo Pool Party, the Beers and Bears Leather Ball and the Mr. Key West Contest and Dance Party! 

Take a look at some of the great photos taken by Larry Blackburn!

  • Key West Bear Weekend
  • Key West Bear Weekend
  • Key West Bear Weekend
  • Key West Bear Weekend
  • Key West Bear Weekend
  • Key West Bear Weekend
  • Key West Bear Weekend
  • Key West Bear Weekend
  • Mr. Key West Bear contest

The Mr. Key West Bear contest will be held on Friday, November 4th at 9:00pm at Bourbon Street Pub, 724 Duval St in the Cabaret Room. 

Join the crowd to see the competition for the title with celebrity guest host Alexander Rodriguez, along with our very special guest judge, one of the most popular OnlyFans Bears out there, Teddy Bear! Teddy Bear also hosts the Bear With Us, GURRL podcast with Alexander Rodriguez, and just starred as a Judge on the first season on the go-go dancer competition show Gogo For the Gold

The winner of this contest receives a $200 cash prize and a handmade leather sash courtesy of Leather Master

Mr. Key West Bear will be expected to raise money and/or raise awareness for a local Key West LGBTQ cause, however you are not required to be a Key West resident. In addition to not being required to be a resident of Key West to enter, contestants are not required to have won any previous titles. However, winning Mr. Key West Bear qualifies you to be able to enter both the North American Bear and World Bear contests! 

So, why not enter and compete to become the next Mr. Key West Bear? Contestants will be judged on the following:


Winning the title is definitely a rewarding experience – It’s a chance to meet new people, do something great for your community, and win that leather sash! 

“It was such a great feeling being able to be a part of bear herstory! It really changed my life!,” says Ryan Acosta aka Poppy J Snacks (they/them), the very first person to win the Key West Bear sash. 

“Winning the 2nd Key West Bear Weekend contest felt bigger than me,” says Pepa Mahogany, Mr. Key West Bear 2019. “I felt like I was winning for all those that were told they didn’t belong to the Bear community because they didn’t fit a certain type of Bear or stereotype. I felt I represented those that are very much part of Bear culture, but also paint with other colors of the rainbow and have a different aesthetic.”

Pepa also had the unique experience of holding the title from 2019 to 2022, where he will be able to hand the sash over to this year’s winner. “Being able to represent my local community and the Bear community at large, I took very seriously. I went in guns a-blazing – and then COVID happened, so then I had to get creative on how to do all the things I wanted to do while still keeping it safe,” he says. “Overall, I’m proud of what I was able to accomplish and it’s certainly been an honor and rare opportunity to be invited back for 3 years.”

When speaking of their experience holding the title for the first time in 2018, Ryan says: “I was able to meet other titleholders and leaders of our community! It really inspired me to get myself more out there – and then I started doing improv and stand up comedy! ” 

And when asked what they would like to see in the next Mr. Key West Bear, the previous winners stated: 

“I would like to see someone that can really continue using the title to inspire and lead! Pepa has been such a shining star during his reign, and I hope the season 3 winner follows in our footsteps”, says Ryan. 

“I hope the next Key West Bear honors the spirit of what Key West is about – and that’s our One Human Family motto,” says Pepa. “I hope they’ll make everyone feel welcome and that they’ll make the journey their own. I look forward to passing the crown and being a support system for them. Just remember to let love lead the way!”

Mr. Key West Bear 2019
Photo by Larry Blackburn

Well,what can we say? We’ve had some pretty amazing Mr. Key West Bear titleholders! Whoever is next will have some big shoes to fill, but we have some amazing Bears in our community, and there is no doubt they will shine bright like these two stars!

So, if you are interested in being the next Mr. Key West Bear, visit the Mr. Key West Bear contest page and register TODAY!

KWBW tickets and passes are ON SALE NOW! CLICK HERE to find out more about All Access and VIP Gold passes! 

For more information about KWBW, visit

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Find all about Alexander & Teddy Bear at

Key West Bear Weekend is sponsored by Bear World Magazine and

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