Smashing Pineapples - Your May Concerts and Events Calendar


May - the month where you can’t totally depend on the weather yet. So how do you make sure you can still have some fun? Planning ahead never hurts (and can earn you a $25 e-gift card).

Here are some of our favorite, weather independent, activities we think are worth your time and hard-earned money. Of course, a Staypineapple hotel is never far from any of these wonderful events.

Let’s go!




Windemere Cinco De Mayo Party on the CUT - University of Washington CUT / May 4th

Enjoy some of Seattle’s top food, booze, and live music the night before one of Seattle’s premiere athletic events, the rowing day of the Windemere Cup. Two Staypineapple hotels are just steps from the boathouse where this event is taking place. (free)

MGMT - Showbox SODO / May 12-13

Showbox SODO is the perfect venue for the popular synth pop group to elevate their melodic sing along choruses that have hooked millennial audiences since the mid-2000s. ($77+)

Seattle International Film Festival - various theaters / May 17th - June 10th

SIFF is billed as the largest film festival in the U.S. Join top directors, actors, and critics who attend festival premieres and screenings by choosing your own adventure with a single show or festival pass! $11+




The Eagles - Moda Center / May 5th

One of classic rock’s greatest bands, The Eagles have joined together once again to play their iconic hits. Maybe they’ll do us a favor and change “Hotel California” to “Hotel Rose”? $31+

Sabroso Craft Beer and Taco Festival - Portland Meadows / May 13th

This tasty festival is headlined by The Offspring and filled with over 100 craft beers, delicious gourmet tacos, Lucha Libre style wrestling and live music! What’s not to like? $50

Paul Simon - Moda Center / May 19th

Catch one of the best singer - songwriters of a generation, Paul Simon, as he performs songs from his decades old catalog. $31+




Bay to Breakers - Through San Francisco / May 20th

Billed as the oldest continuous foot race in the world, the 12K Bay to Breakers starts near the Embarcadero and finishes at the ocean. Expect to see costumes, and to have an amazing time. $70

Spring Wine Pour - Pier 39 / May 18th

Stroll The PIER and stop by participating businesses to enjoy wine tastings, exclusive discounts, and entertainment from 4 – 8 PM. $20

Whitney Cummings -  Cobb’s Comedy Club / May 10th-12th

One of the most successful and biting comedians of the last decade hits San Francisco for multiple shows to share her thoughts on the modern world. $55+





Rhythm and Brews Music and Craft Beer Festival - Historic Vista Village / May 5th

The Rhythm & Brews Music and Craft Beer festival is one unforgettable day, complete with jams from local musicians and tastes of more than 50 of the most renowned breweries from San Diego County and other vibrant craft beer regions around the country. $25+

Spring Sprint Triathlon and Duathlon - Mission Bay and Beaches / May 5th

With a calm bay swim and a flat bike and runing course, the Spring Sprint is the perfect race to kick off your season. $57+

Pink - Valley View Casino Center / May 28th

Pop diva Pink performs her catalog of hits from the past twenty years. Expect aerial acrobatics. $8+





Bike The Drive - Lakeshore Drive / May 27th

Register to ride your bike on 15-mile Lake Shore Drive when it closes to vehicles during Bike the Drive, and join the after-festival until noon at Butler Field. $50+

Night Nation Run - Soldier Field / May 19th

The Night Nation Run is the World’s 1st Running Music Festival an ultimate blend of a music festival and a fun run. Experience a music-filled course with Live DJs, Light Shows, Bubble Zones, Neon and Black Lights. Cross the finish line into an Epic Main Stage After Party featuring Top Headliner DJs. $30+

Jimmy Eat World - Riviera Theater / May 8th

Energetic performers Jimmy Eat World play their angsty, heart stricken rock songs that have gained them popularity since the early 2000’s. $45+




Step Afrika - Emerson Cutler Majestic Theater / May 3rd - 6th

Step Afrika! triumphantly returns to Boston with The Migration, a multimedia powerhouse production that chronicles and celebrates the paths of the brave men and women who left the American South searching for better opportunities. $10+

The Kooks - House of Blues / May 21st

British rockers The Kooks play The House of Blues with their catchy, pop driven rock n’ roll. $23+

Pauly Shore - Laugh Boston / May 10th - 12th

Irreverent funny man Pauly Shore performs for three nights at Laugh Boston, telling jokes and reflecting on his major success in the 90’s. $40+

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