As Portland embraces the warmer days of May, the city comes alive with a variety of events catering to diverse interests. Here’s a curated list of upcoming happenings to mark on your calendar:
Concerts and Performances
Herb Alpert and The Tijuana Brass
Date: Monday, May 11, 2026
Venue: Merrill Auditorium
Legendary trumpeter Herb Alpert brings his iconic sound to Portland for an evening of jazz and Latin-infused melodies. Tickets are available through the Merrill Auditorium box office.
Silversun Pickups – Tenterhooks Tour
Date: Monday, May 11, 2026
Venue: State Theatre
Alternative rock enthusiasts can look forward to Silversun Pickups performing live as part of their Tenterhooks Tour. Secure your tickets early to enjoy this energetic show.
Sports Events
Maine Mariners Playoff Games
Dates: May 15, 17, 19, 21, 29, 31 (subject to change based on playoff outcomes)
Venue: Cross Insurance Arena
The Maine Mariners are making a strong playoff run in the ECHL North Division Finals and Eastern Conference Finals. Support the home team by attending these thrilling games. Check the Cross Insurance Arena’s official website for the latest schedule and ticket information.
Community Gatherings
Summer Sunsets Series
Dates: May 21, 22, 28, 29
Time: 4:00 PM – 8:00 PM
Location: Thompson’s Point
Kick off the summer season with the Summer Sunsets series at Thompson’s Point. Enjoy live entertainment, a variety of food trucks, and picturesque waterfront views over the Fore River. This family-friendly event offers a relaxed atmosphere perfect for all ages.
Art and Culture
“Heritage” Art Exhibition
Date: Saturday, May 16, 2026
Venue: Design Portland
Explore the pop-up art gallery “Heritage,” presented by Ethereal Reflections. This group exhibition features works inspired by themes of inheritance and legacy, offering a thought-provoking experience for art enthusiasts.
Portland Rose Festival
Dates: May 22 – June 28, 2026
Location: Various venues across Portland
The annual Portland Rose Festival returns with a month-long celebration featuring parades, fireworks, and various family-friendly activities. Don’t miss the opening night fireworks show on the Willamette River, a highlight that draws crowds from across the state.
For more details on these events and to stay updated on any changes, please refer to the official event websites or contact the respective venues directly. Enjoy the vibrant offerings Portland has in store this May!

