The Olive Free Library celebrated its fourth annual Library Fair on June 7 with live music, a bustling plant sale, and a performance by juggler and beatboxer “Jester Jim,” drawing families and community members for a day of entertainment and connection.

Jester Jim’s high-energy set—featuring juggling, beatboxing, and comedy—was a standout. Many attendees called it their favorite part of the fair.

Outside the library, food vendors from Hole in the Wall Donuts and Vinnie’s French Fries served snacks across from the popular plant sale, organized by the Friends of the Olive Free Library. The sale raised about $600, all of which will support the library.

Josh and Alanna Slack’s family picked up two dahlias and said the fair’s highlights included the music, especially a pop-up performance by the Dewey Decibel band featuring Jon Coghill.

“We come to most stuff they do,” said Alanna Slack. “We are very involved in the library, because we have little kids.”

A raffle entitled “Keeping Cool in the Catskills” offered summer essentials, including Neutrogena sunscreen and a large bottle of Tito’s vodka.

“It’s always great, in Olive, when the community has an opportunity to get together,” said Town Supervisor Jim Sofranko. “We’re a town that lost our community when they built the reservoir. We’ve lost our town centers over 100 years ago, and it’s always been a struggle to try to find opportunities for the town to get together and interact.”

In a community split by the Ashokan Reservoir that often struggles to get the younger generation involved, facing federal cuts to the Mid-Hudson Library System, Olive is evolving. The library is expanding to include a Shokan branch at Legion Hall to reach more residents and is relying on book donations and hopefully, an increase in the library’s budget.

Library Board Secretary Kim Daley, a candidate for town clerk, and recent board member Dale Crispell staffed a booth to gather signatures for a proposition to increase that budget which would appear on the Nov. 4 ballot. If they receive enough signatures, voters can decide whether to increase the library’s annual budget by almost 50% to $289,642.

Almost 15% of the budget comes from grants, donations, and gifts. The increase means Olive taxpayer money would serve as more stable funding.

“The library is pretty reflective of the community,” Daley said. “With all the committees and all the people visiting and all the people voting, I think it’s a good representation of town.”

In anticipation of the library’s Shokan branch, visitors at the fair could buy books from the Golden Notebook to either keep or donate.

Children and families also visited educational booths, including one hosted by Minnewaska State Park environmental educator Laura Connor, who taught visitors how to identify animal tracks and led crafts using wildlife displays.

Crispell reflected on the library’s cultural role: “Who would have had that experience if the library hadn’t provided it? Those are the types of things that we should be doing,” he said, noting a prior workshop on traditional Indigenous basket weaving.

A display inside the library highlighted local authors, including Library Director Melissa McHugh’s Town of Olive, several works by Glenn Kreisberg, and Hard Times, You Say? Smile, This Is the Great Depression by R. Leslie Howe. Kreisberg is scheduled to return on June 21 to speak about Native American stone structures in the Catskills.

“One of the things I love about our library is that it’s such a community center,” said Susan York, vice president of the library board. “You don’t have a downtown like Woodstock, where people are going to run into each other. There’s so many great things that the library is filling the need for.”

Face painting, ukulele songs, and a basement book sale added to the day’s festive spirit.

“There’s a lot of tension between generational families and new people,” said Sofranko. “These events give people the opportunity to get together, meet each other. The kids play together and suddenly that barrier of tension breaks down.”

Mia Quick is an intern and contributing reporter. You can reach her at reporting@theoverlooknews.com.