‘Bear Weekend’ Brings Furry Fun Back to Key West

Bear Weekend Sunday Tea Pool Party at the Island House. Photo via Damon Scott

One of the most popular entertainers among the bear set is coming to Key West.

Gay rapper Big Dipper is headlining “Key West Bear Weekend” — now in its third year — Oct. 30 to Nov. 3.

There are many reasons why bears should be excited about Big Dipper, event organizer Shane Tate said.

For one, he’s a big body positivity advocate and regularly features plus-size bears in his music videos.

He writes songs about big boys. 

Case in point is his song and video “Thiccness” – a sexy ode to bears. Stermer has been self-producing “provocative queer and empowering music and videos” since 2011.

Tate recommends another song – “Lookin” – to help understand the Big Dipper vibe. 

The artist has racked up millions of views on his YouTube channel and his live show is performed across the globe.

He’s become known as the “go-to bear of raunchy internet rap,” and is in ever-increasing demand at Pride events throughout the U.S.

Bear Weekend will feature other bear-centric entertainment, too, like the Joe Fiore produced Furball dance party – back for the second year.

Popular drag queen Vita Summers will host events as well.

Tate launched Bear Weekend three years ago to “see if the bears could go down to Key West.” 

“We were shocked at how many people were able to make it down,” he said.

That first year about 300 people came. This year’s interest is on track to match or exceed the first two years.

“You never really know how many people will come. You can’t just go by advance ticket sales, because some people don’t buy the passes until they arrive,” Tate said.

At press time about 100 passes had been sold – similar to the same point in 2018.

Bear Weekend has previously been held the week before Key West’s Fantasy Fest (this year Oct. 18 to Oct. 27), but that presented challenges because hotels raise prices and airfare is high, Tate said.

“For example, New York to Key West was like $1,300, so this year we worked with hotel owners, the city and the gay chamber who were really helpful,” Tate said.

He’s got four hotels participating in group rates so far.

Bear Weekend is now scheduled to land after Fantasy Fest, when hotel rates and airfare are typically lower, Tate said. 

With the new dates comes a new event, too – Bear World Magazine’s “Monster Ball” at the Bourbon Street Pub on Duval Street. Also new this year is a foam pit, which Tate said will be “interesting.” 

Attendees can expect a wide variety of gatherings and another Mr. Key West Bear contest and party – this time held in what would be considered a cabaret room at the Bourbon Street Pub.

Other notable options include the:

  • Bear Soup Pool Party at the Island House.
  • Kingdom of Neptune Pool Party at the Equator Resort.
  • Bear Ass Tea Party at the Island House.
  • Farewell Party at the Island House.

While Tate has lived in New York since the late 1980s, he was born in Jacksonville and previously lived in Miami and South Beach. He’s also the force behind “Fire Island Bear Weekend.”

Tate said Key West is an impressive place.

“It’s a resilient city that’s back up and running. You wouldn’t know [Hurricane Irma] went through there,” he said of the massive 2017 storm.

There are many single ticket or day and weekend pass options on each day of the long weekend. Go to KeyWestBearWeekend.com for all the details.


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