Our Monthly Picks Around Town: May 2026

Monthly Picks

Apr 21

May is bursting with things to do across Portland, and we've rounded up some of our favorite picks to help you make the most of the warmer weather! Whether you're looking to explore open streets on two wheels, discover local art in a charming neighborhood, dig into Portland's history, or simply enjoy a classic fair with the family, there's something for everyone this month. From free community celebrations to culturally rich festivals, May is shaping up to be a great month to get outside. Mark your calendars and get out there!

MOTHER’S DAY RHODODENDRON SHOW
May 9th-10th | Chrystal Springs Rhododendron Garden

This decades long tradition features a large plant sale and judged flower show. Stroll in the tranquil gardens featuring rare species and hybrids during peak bloom season. A perfect Mother’s Day weekend event!

PORTLAND INDIGENOUS MARKETPLACE
May 9th | Native Arts and Cultures Foundation

Support Indigenous and Black artists and entrepreneurs making the community vibrant. Find unique art, apparel, jewelry, performances and more with a raffle and food vendors. Free admission!

PORTLAND SUNDAY PARKWAYS
May 17th | Multiple SW Portland Locations

This free, all ages event kicks off with a 2 mile walk/bike route highlighting SW Portland trails. Enjoy live entertainment, vendors, and family-friendly activities. A beloved spring tradition!

MT. TABOR ART WALK
May 16th-17th | Several SE Portland / Mt. Tabor Locations

This annual event is a great way to view and purchase high-quality art, meet the artists, and spend a fabulous spring day walking through the historic Mt. Tabor neighborhood. Featuring photography, ceramics, metals arts, glass and much more!

VANPORT MOSAIC FESTIVAL
May 22nd-31st | Various Portland Locations

Explore Portland’s silenced histories and celebrate community resilience. This powerful and moving experience of “memory activism” includes performances, documentary screenings, exhibits, tours, dialogues, and more.

MULTNOMAH COUNTY FAIR
May 23rd-25th | Oaks Park

Get ready for a fun packed weekend at Oaks Park! Enjoy rides, exhibits, and performances including live music, dance troupes, Portland Lucha Libre, a Doggie Parade, and Costume Contest. There’s something for everyone in the family!