Chrisi Gaskill and Jessica Caldwell discuss a recent game of Island Trivia. Photo: C. Leinbach

By Connie Leinbach

The Island Trivia nights on Ocracoke are not just for fun.

They raise money for an Ocracoke School graduating senior in honor of a late island resident who loved trivia nights.

That person was Phyllis Wall, a vivacious octogenarian and avid player who died in 2021. The scholarship given out at graduation is the Phyllis Wall Scholarship Fund.

All the money collected to play the bi-weekly games goes toward the fund and all of it is given out each year, said Chrisi Gaskill, who with Jessica Caldwell, run the games.

Caldwell and former island NPS ranger Jocelyn Wright started it in 2007, Caldwell said.

After Wright left the island, Sara Batchelor assisted and later Gaskill joined.

This year, the two had a goal for the fund to reach the milestone amount of $2,000, which Caldwell reported they reached earlier in June.

Gaskill and Caldwell don’t rely on anything prefab as they devise all of the questions and categories on their own.

Caldwell had the idea of categories with themes instead of broad outlines.

“Sometimes we get inspiration from ‘Jeopardy!’ categories,” Gaskill said.

She has a connection to that television game show since her fiancé, Charles Temple, won the first ever Teacher’s Tournament in May 2011 and to which she accompanied him on his trip to Los Angeles.

“She’s really good at coming up with category themes,” Gaskill said of Caldwell. “On average, there’s one question (during each game) that no one gets.”

It’s not a chore for them as they might work on questions a few hours each day and weeks in advance.

“I love doing it so much,” Caldwell said.

The duo offers a hint to winning: Have a team with a spread of ages.

The pair conducts team trivia most of the year except for January and February. Games are played at 1718 Brewing Ocracoke until Ocracoke Coffee Company/Mini Bar opens in season.

Dates for Island Trivia this month are June 12 and 26 and every other week after that through the summer at the Mini Bar.

Those who can’t play but want to contribute to the fund can send checks made out to Ocracoke School with “Phyllis Wall Scholarship Fund” in the memo line and send to the school at P.O. Box 189, Ocracoke, NC 27960.

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