Explore the Best of Portland: Top Events and Activities from May 20-26, 2026

Portland, known for its vibrant cultural scene, eclectic neighborhoods, and passion for community events, is gearing up for an exciting week from May 20 to 26, 2026. This week promises a myriad of activities catering to diverse interests, from music lovers and art enthusiasts to families and thrill-seekers. Whether you're a local or just visiting, there's something for everyone in this dynamic city.

For music enthusiasts, the Lunchtime Concert at The Old Church is a must-visit. This historic venue has been hosting free lunchtime concerts for over 56 years, featuring members of the Oregon Music Teachers Association. On May 20, these talented musicians will perform a variety of classical piano music, offering a serene break amidst the bustling city life. The Old Church Concert Hall, located at 1422 SW 11th Ave, is not only an acoustic gem but also a piece of Portland's rich history, making it the perfect setting for an afternoon of classical music.

Storytelling is an art form that brings people together, and Backfence Storytelling at Powell’s City of Books is the perfect event for those who appreciate the spoken word. On May 21, the iconic Pearl Room will host an evening of storytelling with a lineup of talented narrators, including Ash Allen and Candice Rose. With a full bar available and a 15% discount on book sales for ticketholders, this promises to be an engaging and entertaining evening that combines literature and performance.

For fans of body art and tattoo culture, the Void Tattoo Fest is a unique event that offers an unconventional artist-run expo. Taking place at Jupiter Next and Jupiter OG from May 22 to 24, this fest features top-tier tattoo artists from around the world, expert seminars, art shows, and creative vendors. Each motel-style room is converted into a mini tattoo shop, providing an intimate setting for artists and attendees to connect and appreciate the art of tattooing.

Families and fun-seekers will find their haven at the Multnomah County Fair, happening at Oaks Park from May 23 to 25. This three-day event is packed with competitive exhibits, musical performances, stage shows, and the ever-popular Lucha Libre wrestling. Additionally, visitors can explore a pioneer village, enjoy small animal activities, and indulge in a variety of delicious foods. The fair also includes the Thrillsville amusement rides, ensuring a day filled with entertainment for all ages.

Skateboarding is more than a sport; it's a community, and the Push Movement Block Party on May 23 celebrates this spirit. Organized by Push Movement, an organization supporting skaters in recovery, this event is both a celebration of successes and an opportunity for the community to come together. Whether you're a seasoned skater or just a supporter, this block party promises to be an uplifting and fun experience.

Lastly, for fans of comics, graphic novels, and gaming, the Westside Comic Con offers a platform to celebrate and promote these popular arts. Held at the Wingspan Event and Conference Center in Hillsboro on May 23 and 24, this con is a chance for the community to mingle, attend seminars, and explore the latest developments in the world of comics and gaming.

In conclusion, Portland from May 20 to 26, 2026, is a city that has something for everyone. From the serene sounds of classical music to the vibrant colors of tattoos, and from the thrill of skateboarding to the imaginative worlds of comics, each event embodies the city's spirit of community, creativity, and inclusivity. Whether you're a local or just passing through, make sure to check out these events and experience the best of what Portland has to offer.