It’s here, it’s here: the worst day of the year! Over 4,000 Portlanders will peddle in the Worst Day of the Year ride, a Portland winter tradition. Bring the family out to root for the riders and enjoy entertainment, food and the costume contest. In the mood for Valentine’s Day? Find something sweet and handmade for yourself or a loved one at The Crafty Underdog, a family-friendly event dedicated to the heart of local art, craft, and trade. Where can you see local kids music faves Mo Phillips, Toy Trains and The Alphabeticians while you enjoy juggling, magic, kitemaking AND get your kids fitted for inexpensive snowboard and bike helmets? The grand opening party of the Randall Children’s Hospital at Legacy Emanuel. It’s truly a place where love for family and children is celebrated all year round.

East side

Worst Day of the Year Ride (featured; photo credit, Community Cycling Center)
Get ready to ride with (or cheer on!) 4,000 other fun-loving people for the Worst Day of the Year Ride, an 18-mile odyssey around downtown Portland. Sun. 8:00 am – 4:00 pm. Lucky Labrador Brew Pub (Hawthorne). Free to watch. See site for racing details and pricing. All ages. Event details.

Randall Children’s Hospital Celebration
Bring family and friends to celebrate our new home! Entertainment includes music, grand prize drawings for family trips, scavenger hunt, LEGO play zone, kite making and photo booth and low cost bike and snowboard helmet sale and fitting. Sat. 12:00 pm – 6:00 pm. Free. All ages. Event details.

The Curious Garden
Come see our old friends Razzie the Fairy, Daisy the Flower, and Jojo the Lawnjockey; and meet our new garden friends Ribbit the Frog, Dottie the Ladybug, and Flappy the Chicken! The show ends with an open mic session. Sun. 10:00 am – 11:00 am. Curious Comedy Theater. $5 suggested donation. All ages. Event details.

West side

Crafty Underdog at The Mission Theater
The Underdog returns! Browse from over 30 local artists and makers while enjoying live music, local films, craft brews and food, and kids’ crafts. Sun. 11:00 am – 5:00 pm. Free. All ages. Event details.


Butterfly Girl Day
Kaleela Thompson (a 12 year-old butterfly expert) will share her knowledge and passion for butterflies. She wrote the book Oh Where Oh Where Is My Swallowtail?, which is used by private and public school systems, and she also hosts an online blog talk radio show called Garden Kids. Sat. 1:00 pm – 2:30 pm. Evergreen Aviation and Space Museum. McMinnville. Free with admission. All ages. Event details.

Owl Prowl
Journey into the forest at night to look and listen for courting owls. Watch a slideshow, listen to recordings of owl calls, and see preserved specimens up close. Fee is a family rate and covers one adult and up to two additional family members. Sat. 6:00 pm – 8:00 pm. Nature Park Interpretive Center. Beaverton. $17/family of three All ages. Event details.

–Cheyenne Terbrueggen