It doesn’t get much more Portland than a hilarious, costumed bike ride in the middle of winter. But, if you’d rather stay inside, all warm and cozy, we won’t judge. There’s a famous collection of performers, including jugglers, clowns and contortionists showing up to benefit Clowns Without Borders that promises belly laughs for all. There’s also an authentic Hawaiian celebration, as well as a super sweet, daddy-daughter night out. Read on to discover our top picks for this weekend.

Worst Day of the Year Ride Portland photo: Worst Day of the Year Ride by Good Sport Promotions

East Side

Rain Gear + Wigs = The Worst Day of the Year Bike Ride
Grab your costumes, dress up the kids and join in on one of Portland’s most beloved, wacky winter events. Community Cycling Center’s iconic bike ride will take riders along one of two courses, a 15-mile urban ride and a 46-mile challenge course. The optional Pre-Ride Party and registration on Saturday kicks things off at Lucky Lab. The rides then start at staggered times on Sunday, with plenty of rest stops and bike support along the way. If pedaling on their own, kids under 14 must be accompanied by an adult and the entry fee is the same as an adult’s. Kids being pulled in trailers and tagalongs have a reduced fee. Because this is Portland, costumes are highly encouraged. The costume contest will have prizes for Best Group, Best Weather-Themed, Funniest/Punniest and People’s Choice. Helmets for all riders are required. 2-4 p.m. Sat., 8 a.m.- 4 p.m. Sun., $35-$45/person, All Ages. Event details. 

Laugh it Up at the Clowns Without Borders Benefit
Get ready to laugh yourselves silly at this 16th annual benefit for Clowns Without Borders – USA, a troupe of performers offering laughter in areas of crisis around the globe. The entertainment lineup includes a star-studded cast of world-famous clowns, jugglers, comedians, a lasso pro, acrobats, plate spinners, a hand-balancer and a saxophone-playing tap dancer. Fri., 7:30-9:30 p.m., $9-$30/person sliding scale, All Ages. Event details.

Sealants Free-For-All: Give Kids a Smile Day
Seven Kaiser Permanente offices around Portland, Vancouver, Salem and Longview will be offering up free sealants, flouride varnishes and vaccinations to uninsured and under-insured metro area kids for Give Kids a Smile Day. The clinics coincide with National Children’s Dental Health Month and are offered in partnership with the American Dental Association. No insurance necessary, but your insurance won’t be charged if you do have it. First come, first served. See the website below for details and locations. Sat., 8 a.m.-1 p.m., Free, All Ages. Event details.

West Side

Staycation Destination: KIAKO Foundation’s Ho’ike
Get a little of that aloha feeling without stepping foot on a plane.The KIAKO Foundation’s 9th annual Ho’ike is an authentic showcase of Hawaiian culture, complete with a delish Hawaiian dinner, live music, a silent auction and Polynesian dancing. Can you hear the ukuleles yet? Sat., 5-8 p.m., $40, All Ages. Event details.

Set Sail for Daddy-Daughter Night – Bon Voyage
Choose one of two nights this weekend for a special night with dinner, music and activities for daddies and their sweet little girls. Vegetarian options will be available, as well. Advance registration required via website. Sat. 6-8:30 p.m.; Sun. 5-7:30 p.m., $19/pair (residents); $26.25/pair (non-residents), Ages 3 and up. Event details.

Does your family go on the Worst Day of the Year Bike Ride?  Let us know in the Comments section below!

— Suzie Ridgway