Smashing Pineapples - Your May Concerts and Events Calendar


May is here. That means we’re knocking on the door of summer.

Even better, Staypineapple cities around the country aren’t waiting to put on fun events and concerts - there’s plenty of awesome festivities happening now!

Here are few ways our cities are celebrating May including Mother’s Day, Cinco De Mayo, and Memorial Day. And don’t forget, if you need a place to lay your head at the end of the fun, you can get the lowest rate at our hotels when you book direct!


Cinco De Mayo at The Maxwell - May 5

Swing into The Maxwell Hotel and enjoy a specials menu that includes $6 Silver Patron margaritas, chili relleno pizza, carne asada tacos, and more!

Get painted as you run - May 12

Wear a white shirt, and then get bombarded by handfuls of colored cornstarch as you run the 5K Color Run, which begins at Seattle Center.

Folklife music and dance - May 24 - 27

Celebrate traditional arts by attending some of the hundreds of dance and musical performances, workshops, and panels from around the world held at Northwest Folklife Festival at Seattle Center. Donation encouraged.


Cinco de Mayo Fiesta - May 3 - 5

Enjoy live entertainment, authentic food, carnival rides, an artisan village, and family fun at Cinco de Mayo Fiesta at Tom McCall Waterfront Park.

Lightning Thief - a mythological rock musical -May 7 - 8

“An action-packed musical with heroic battles and mythological beasties” [New York Post], The Lightning Thief features a hero (Percy Jackson) who “has newly discovered powers he can't control, has monsters on his trail and is on an epic quest to find Zeus’s lightning bolt to prevent a war between the gods” at Keller Auditorium.

Rose Festival Kickoff with CityFair & fireworks - May 24 - June 9

CityFair has fireworks on opening night (May 24), carnival rides, exhibits, beer, a food fair, and music concerts at Tom McCall Waterfront Park - right next door to Hotel Rose! No pets. (Closed May 28 to 30, and June 3 to 6, 2019.)

San Francisco

Waterfront beer festival - May 10 (7 to 11 p.m.)

SF Maritime Beerfest has unlimited beer tasting, entertainment, food vendors, and views at Pier 45.

Carnaval San Francisco - May 25 - 26

Carnaval San Francisco celebrates Latin & Caribbean culture with a weekend festival of music, art, and food on Harrison Street (from 16th to 24th Streets), plus a colorful Grand Parade 9:30 a.m. on Sunday. Free.

Memorial Day celebration - May 27

Memorial Day Ceremony includes a 10:30 a.m. Grand March from the Presidio Officers’ Club to San Francisco National Cemetery for 11 a.m. speeches and music, followed by a 21-gun salute at noon, and then a picnic with food for sale on the parade ground until 2 p.m.

San Diego  

Eat Drink Read - May 2

Experience imaginative dishes created by the most popular chefs from every corner of San Diego County, with each bite inspired by the chefs' favorite books. Eat.Drink. Read. is the San Diego Council on Literacy’s annual culinary event that brings together friends of food and literacy every spring to raise literacy awareness and generate funding for the SDCOL’s ongoing efforts.

Cinco De Drinko - May 5

SUNDAY FUNDAY FIESTA STYLE at the Tin Roof. It's not officially summer until we celebrate Cinco! We'll be kicking things off with John Hull on Acoustic then cranking things up with back to back DJ sets from our friends Jwin and Ace. Let's not forget about drink specials! No Cover!

Mother’s Day Brunch cruises - May 12

Sit back and celebrate Mother's Day with a relaxing brunch cruise on the Big Bay in America's finest city. Your mother will be dazzled by the experience of boarding champagne, gourmet food selections, live music and scenic waterfront views aboard our luxury yacht.


Food trucks and wine tasting at the zoo - May 11

The Food Truck Social features dozens of trucks selling food and beverages, plus activities, DJ music, and an opportunity to wander Lincoln Park Zoo after hours.

Memorial Day Parade - May 25

A wreath laying ceremony is 11 a.m. on Daley Plaza. The Memorial Day Parade at noon has high-school marching bands, drum and bugle corps, veterans’ groups, and active duty military on State Street (from Lake to Van Buren). Free.

Whiskey tasting - May 31

Taste 60 whiskeys and hear the band St. Paul & The Broken Bones at WhiskyX Chicago, with food trucks and restaurant food for sale at Revel Fulton Market for ages 21+.


Power Beer Fest -May 4 (1 to 4:30 p.m.)

Taste beer from the 60 brewers who run the Power Beer Fest, with food truck fare for sale at the Castle at Park Plaza for ages 21+.

Wake Up The Earth Festival & parade - May 4 (noon to 6 p.m.)

Celebrate Spring’s return at Wake Up the Earth Festival, with an 11 a.m. people’s parade, six performances stages, craft booths, and food vendors at SW Corridor Park (between New Minton Street & Lawndale Terrace). Donation.

Duckling Day parade - May 12 (noon)

Families celebrate the Boston-based book “Make Way for Ducklings” by registering to join the Duckling Day Parade, which begins on the Boston Common at the Parkman Bandstand and ends in the Public Garden near the famous bronze duck statues, rain or shine. Wear yellow, and enjoy playtime 10 a.m. to noon.

New York City

Taste of the Lower East Side - May 9 (6 to 10 p.m.)

Enjoy unlimited tastes from 50 local restaurants plus open bars at the Taste of the Lower East Side in Metropolitan Pavilion for $195+ to support charity.

Festival of the Arts - May 24 - 26

Lower East Side Festival of the Arts features dance, film, music, poetry, theater, and visual art at the Theater for the New City. Free.

Mamapalooza Mother’s Day Celebration - May 26

Mamapalooza offers music, art, kids’ activities, food vendors, and crafts for mothers and the people who love them at Riverside Park South. Free.