May on the Eastside arrives in full bloom — warmer evenings, longer weekends, and a packed lineup of outdoor happenings that turn neighborhoods into celebration hubs. From weekend street fairs and open-air concerts to Mother's Day brunch specials, community garden plant swaps, and late-night art openings, this month’s picks spotlight family-friendly fun, date-night ideas, and can’t-miss local launches. Grab your sunscreen and a calendar—here are the best events to make the most of May on the Eastside.

Every month we put together a comprehensive list of community and special events happening across the Eastside in cities like Kirkland, Bellevue, and Redmond …

May 01-03: Grease Live in Issaquah

May 01: Mercer Island Art Walk

May 02: Mill Creek Beer & Wine Walk

May 06: Issaquah Wine Tasting

May 08-09: Amazing Drone Show in Redmond

May 09: Eastside Plant Sale

May 09: Issaquah Walk n’ Wag

May 09-10: Bellevue Ballet Presents Alice in Wonderland

May 14: Wine Walk in Old Bellevue

May 16: Sammamish Big Truck Show

May 17: Eastside African Festival

May 21: Best of 425 Party

May 23-31: Outdoor Concerts at Marymoor Park