Fun & Wargames

Looking for a new hobby during these bleak winter months?

Since its August opening last year, the Jester’s Keep has been a haven for tabletop gamers of all ages. Gameplay has been especially popular the month after Christmas, when the coldest weather has hit the island.

Owners Kyle Casara and Juliet Dillard describe the opening of their store in Bayview as a “strange happenstance.” The couple moved from New Mexico to Whidbey to care for Dillard’s father in September 2018. When he passed away, they were torn about what to do next.

“We kind of rolled the dice so to speak and decided to open a game shop, because we love playing games,” Casara said.

The first-time business owners have been busy ever since, hosting weekly tournaments for Warhammer, Dungeons and Dragons, and Magic: The Gathering.

Casara leads six different groups for Dungeons and Dragons, totaling about 30 people. Warhammer’s following is also growing.

Among the clatter of dice, seventh graders Harper Neff and Griffin Arndt play a round of their favorite game on Warhammer Wednesday inside the Jester’s Keep.

“I like coming here because it’s a place where you can go after school just to hang out and play something,” Neff said, “because my house is a bit crowded and his house has small tables.”

The best friends since birth spread out their miniature models and pieces of terrain across a large table. Armed with a guide book and a measuring tape, they roll the dice and contemplate their next moves across the battlefield.

“It’s a bit like absurdly complicated chess,” Neff explained.

The miniature models, which can be purchased within the store, are usually hand-painted. Arndt said some are easy to paint, but others are much harder.

Formerly a yoga studio with a stretching bar still attached, the walls of the store have been repainted to capture “a castle feel, but vibrant,” Casara said.

Although the Jester’s Keep has a heavy focus on tabletop gaming, the store also sells jigsaw puzzles, board games and cards. Casara said he is a fan of games in all forms, from mobile apps to video games to board games to tabletop games.

“We play games together at the shop, we play games together at home,” he said about himself and Dillard.

The journey has not all been “fun and games,” though. Casara works as a line cook four days a week at Saltwater to help support the store. His grandfather and father have both owned restaurants, which was where he met his wife. Opening a game store together helped them to escape the “black hole of restaurants.”

“I had the customer service background, and he had the more business end of it covered,” Dillard said about her husband.

She added that starting a business has been “exciting and nerve-wracking and terrifying,” all at the same time.

Warhammer is played on Wednesdays and Sundays, Dungeons and Dragons on Wednesdays and Thursdays and Magic: The Gathering on Friday nights. All other days except Tuesday are available for open play.

Players are welcome to rent sets or bring their own to the Jester’s Keep. Casara said they are always open to trying new games.

People of all ages have flocked to the store, from middle schoolers to retirees.

“So far, I’m hearing this is a much needed place for Whidbey,” Casara said.

Jester’s Keep owners Juliet Dillard and Kyle Casara play their own game of Warhammer.

Jester’s Keep owners Juliet Dillard and Kyle Casara play their own game of Warhammer.

A row of expertly hand-painted miniature models used in a typical game of Warhammer, painted by Jacob Bloom, can be found at Jester’s Keep.

A row of expertly hand-painted miniature models used in a typical game of Warhammer, painted by Jacob Bloom, can be found at Jester’s Keep.