As Memorial Day passes us by, it officially starts to feel a bit more like summer. This week of May 25-31 fills your schedule with Pittsburgh events that inch you closer to June by getting you out and about. It’s a week to remember for our art fans, book lovers, Grease aficionados, and more.

Pittsburgh Events Happening May 25-31

Teen Night: Building Block Party

May 28, Kamin Science Center

As your teens get closer to summer vacation, help them celebrate early at the Kamin Science Center’s Building Block Party. This free event for ages 13-18 lets your kiddo chow down on cookout style food, play backyard games, and then try to solve engineering challenges. It’s a chance to let your teen have their own time to socialize away from the parents as the excitement of break is on the horizon. 

Grease: Outdoor Movie & Live Choir Sing‑Along

May 29, The Great Lawn at The Frick Pittsburgh

The 1978 movie/musical, Grease, is loved by those young and old. Now you can see this classic on the big screen like never before. Bring a blanket or chairs to lounge out on the lawn, and make sure to wear your best poodle skirt or leather jacket for this outdoor screening. Not to mention, The Pittsburgh Concert Chorale joins the stage to provide a live choice sing-along, backing up each and every song with harmonies. 

Pgh Book Fest 2026

May 30, Carnegie Library of Pittsburgh — Main

Calling all book lovers, the event of the year is here to make all your literary dreams come true. The Pgh Book Fest brings authors from all over the world right to Pittsburgh for discussions, panels, workshops, as well as book signings. Whether it’s a Pulitzer Prize winner or an indie author, you’re sure to find a brand new book to take home after a day full of shopping, listening, and connecting with other bookworms. There are even special readings and events for the kids too.

Riverlife Chalk Fest 2026

May 30-31, North Shore

After four years of stunning chalk imagery, the Riverlife Chalk Fest is back for its fifth year. Let yourself soak in the color and art of the city as you walk through two large chalk zones full of works portraying your favorite cartoon characters, realistic portraits, optical illusions, landscapes, and so much more. Plus, you can enjoy local food options, beverages, live music, and plenty of family-friendly fun while you’re there. 

Spring Fling Market

May 31, Armful of Flowers

Spring is in full swing which makes this the perfect time for shopping at the Armful of Flowers’ garden center and flower bar. They’ll also be showing off the farm with farm tours and walks. On top of Armful of Flowers’ offerings, you can additionally walk through vendors from around the city selling art, jewelry, home goods, and fashion. On top of it all, you can get into the spring spirit with themed drinks and food as well as live entertainment for all ages.

Plus, check out our calendar for other events for the week and beyond!

Story by Kylie Thomas
Featured Photo Courtesy of Armful of Flowers

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