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It might be interesting to do a type of play. Like in the Fountaindale Library Friends group interactive mystery plays.
Maybe not the best idea with Covid but when this is done hopefully.

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I think a fun reoccurring fundraising event that a library could do would be movies in a park. They could do different themes - Lady's Night Out, Fella's Night Out, Family's Night Out, etc. At the movie event they could sell concessions, t-shirts, and even do different raffle baskets. It would be a fun way to get community members out while also raising funds for the library. Getting businesses involved to sponsor and donate snacks would definitely help elevate any costs for the library to put it on, making for more gains. It would definitely be important to assign clear roles and break down the work into manageable tasks ahead of time: Making flyers, designing shirts, reaching out to local businesses, setup, running concessions, cleanup crew, etc. Definitely a lot of planning and organizing to navigate as a team, but something that could be very successful for a library.

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I think it would be a fun idea to do the fundraiser with adults in mind. With that being said I think a wine tasting would be interesting. Only people over the age of 21 would be able to attend. You could have cook books using wine, including how to cook with it and how it is made, what wine to choose with different meals, and how to grow a vineyard. You can charge customers either for the wine itself or admission to the fundraiser. Upon further inspection I found that an idea like this used to be offered at the bethel library but was stopped after 2006, I would definitely recommend this be brought back and implemented it at my local library.

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A library in Abbotsford, Canada had their eighth annual bridge tournament. The library raised over $350 dollars during their last tournament through the eighty-eight contests that showed up to play. I am not a huge fan of bridge, but having game tournaments seems like a fun and exciting way to raise money. I am not sure if this is legal because of gambling laws, but hosting a casino night would be great, especially if the library had a poker table set up.

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A fun fundraiser event would be having board game tournaments that are "pay to play" and would benefit the library. Friends of the Saint Paul Public Library hosts the annual Crossword Tournament each year.

With COVID going on, maybe their would be some way to set up an online game where donations would be submitted digitally and games could be played online.

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The public library of Newington Connecticut, Lucy Robbins Welles Library at their annual book sale. At the senior center, which is across the street from the library, they invited well-known vendors of gifts and personal items to display their wares. A portion of the proceeds went to the Friends of the library.
If possible the fair could still go on, but with certain accommodations: vendors are six-feet apart from each other, all are required to wear masks, gass shields are at the vending booths, and only a small group of people are allowed in at a time.

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Fun Run/Scavenger Hunt   Donna Aschebrock

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Fun Run/Scavenger Hunt   Donna Aschebrock

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I think a fun run/ scavenger hunt would be a fun way to raise money. Participants would all receive a t-shirt with the names of donors printed on the back. Area business and community members could get involved by hiding the items to be hunted. Clues as to what to search for could be hidden around town and participants could work in teams or individually with prizes for the winners.

"Like a mountain range Appalachia and Andes
come find me and get some candy"
This is a clue to go to Rocky's Bar for an piece of Andes candy.

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Libraries could create fun gift baskets filled with things like books, gift cards, snacks, baking mixes, socks, candles, etc. for  different ages and raffle them off to raise funds for the library. These baskets could be themed for different holidays like Halloween and Christmas.
Gift basket raffles typically go over very well in the small towns around where I live and are something enjoyable for both the library and the community.
My extended family recently had a larger scale gift basket raffle and raised a few hundred dollars to help pay for a relative's extensive hospital bills. They also added in a silent raffle and raised a couple thousand dollars off of that.

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Virtual Valley History Trivia (Krister Paakkonen)

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Virtual Valley History Trivia (Krister Paakkonen)

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The public library in Eau Claire has already partnered with the local historical Chippewa Valley Museum to provide public access to its large collection of photos depicting life in and around Eau Claire. Why not put this great resource to use?

As many community members are interested in local history, this would be a great fundraising project organized by Friends: an online tournament called Virtual Valley History Trivia. Thanks to the resources of the library and the museum it would be easy to promote the event(s) via their websites and social media accounts. As both organizations have volunteer organizations, it could also be a new kind of collaboration between them.

For this event you would recruit and possibly attract new Friends volunteers of different ages, some who have digital technology skills and artistic interest, as well as older members who have personal memories to draw on and write really initiated questions. The project would also fulfill the criteria of a finite and hands-on project which appeals to today's volunteers (as mentioned by Sally Gardner Reed in the “Making ‘Friends’ with Today’s Volunteers” video.)

The game would focus on guessing where and when the photos were taken, and additional questions about all kinds of historical trivia related to the pictures. The meeting rooms function in Zoom could be used to put the teams into “breakout rooms” to confer during e.g. 1-2 minutes. This way the experience would be similar to a fast-paced TV game show. Why not even invite a local musician to compose and record an original theme and music during the teams' thinking sessions?

The teams would pay an entry fee, and could be made up of private citizens or maybe even be sponsored by local businesses and organizations—a great way to hike up the participation fees. The event could end up being a “triple-win” situation: local businesses contributing with game prizes, as well as promoting the library’s special collections and the museum’s holdings.