98110: The Community of Cups Espresso & Cafe


Poulsbo was the first home of Cups Espresso & Cafe (formerly Checkers Cafe). Sean and Wanda Winkers eventually expanded their warm business to Bainbridge Island and established their second location in 2016. As their horizons broadened by the end of 2017, new visions (including ice cream!) took flight for Cups’ offerings. In March of 2018, the Winkers sold the business to its current family of owners, whose intentions are to continue the Winkers’ tradition of bringing together cozy, community gathering spaces, delicious food, and friendly service.


More than just a coffee shop, they make all their pastries, quiches, and stratas fresh every day. Cups invites you to indulge in their signature and rotating selections of items, like handcrafted sandwiches, lemon drop cookies, quiches, Cascade Glacier ice cream, and açaí bowls. Caffe Umbria supplies them with coffee directly from its roastery in the Georgetown neighborhood of Seattle, which uniquely blends varietals from around the globe.


Between organizing various donation boxes for island charities and programs, displaying artwork from regional photographers, and hosting a myriad of local groups, they believe in whole-heartedly supporting their community. To name a few, they have opened their space up to an arts group, music lessons, live musicians, quartets, and a weekly folk music jam session.


As people work remotely from their cafe and regulars order their favorite drinks, tourists wander in while exploring the island for the first time. Whomever their guests may be, the Cups staff ensures everyone walks away feeling welcomed. Though compliments on their coffee and food are sincerely appreciated, their foremost gift to the community is quality service.


As 2020 rounds the corner, Cups will branch out its menu with an assortment of handcrafted panini melts. Further, they will host more live music and events as well as create fun, community outreach programs focusing on literacy in young readers and supporting disabled individuals in Kitsap County.

The well-trained, supportive team at Cups aims for the cafe to become known as the friendliest place on the island. Stop in to be a part of making such a dream come true!



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