Labor Day Weekend, August 29–September 1, is the perfect chance to enjoy Portland before the kids’ backpacks start filling with homework instead of snacks. With free festivals, outdoor adventures, and interactive attractions, the Rose City has plenty of ways to keep kids entertained (and maybe tire them out enough for an early bedtime). Below is a list of confirmed or annually recurring family-friendly events to make your long weekend memorable—and slightly less chaotic.
1. Explore the Art in the Pearl Festival
- When: Aug 30–Sept 1, 10 AM–6 PM
- Where: North Park Blocks, Pearl District, Portland
- Cost: Free
This beloved arts and crafts festival transforms the Pearl District into a giant outdoor gallery. Over 100 artists showcase their creations—paintings, jewelry, ceramics, and more. Kids can paint, craft, or glue sparkles onto something you’ll “treasure” forever. Food carts serve pizza and ice cream (aka the holy grail of kid cuisine).
Tip: Arrive early, bring a reusable bag, and maybe brace yourself for the inevitable glitter explosion.
2. Wander the Dahlia Festival
- When: Aug 29–Sept 1, 9 AM–5:30 PM
- Where: Swan Island Dahlias, Canby
- Cost: Free
With 40 acres of dahlias in full bloom, this festival is like stepping into a floral screensaver. Parents will marvel at the colors while kids treat it like their personal obstacle course. There’s live music, face painting, burgers, and snow cones—basically, summer’s greatest hits.
Tip: Pack sunscreen, a picnic, and maybe a notebook for the kids to “sketch” their favorite flower (read: doodle).
3. Watch the Vaux’s Swifts at Chapman School
- When: Aug 29–Sept 1, dusk (~7:30–8 PM)
- Where: Chapman Elementary School, Portland
- Cost: Free
Thousands of birds swirling into a chimney? Sounds like a Disney movie directed by Alfred Hitchcock. Families gather on the school lawn for this nightly spectacle, where kids ooh, aah, and occasionally chase each other instead of the birds.
Tip: Bring snacks, blankets, and binoculars. Arrive early for the best view—and so you don’t end up explaining to your kids why you can’t just “scoot over a little.”
4. Visit the Oregon Zoo
- When: Aug 29–Sept 1, 9 AM–6 PM
- Where: Washington Park, Portland
- Cost: $24/adults, $19/kids 2–11, free under 2
Elephants, giraffes, penguins, and (if you’re lucky) the rare sight of your child forgetting about their iPad for a whole hour. The zoo also has a Discovery Zone with climbing structures, plus a train ride that’s a hit with all ages.
Tip: Buy tickets online to skip lines, and definitely bring a stroller unless you want to carry 40 pounds of tired toddler around hilly terrain.
5. Get Hands-On at OMSI
- When: Aug 29–Sept 1, 9:30 AM–5:30 PM
- Where: SE Water Ave, Portland
- Cost: $15/adults, $10/kids 3–13, free under 3
OMSI is where “don’t touch that!” becomes “please, touch everything!” With science demos, planetarium shows, and a playground for the littles, it’s educational fun disguised as play. Parents can even sneak in some science facts to make themselves sound smarter at dinner.
Tip: Plan for at least 2–3 hours (longer if your child discovers the word “again” in the planetarium).
6. Pick Fruit at Bella Organic Farm
- When: Aug 29–Sept 1, 9 AM–5 PM
- Where: Sauvie Island
- Cost: Pay by the pound
Berry-stained fingers, hayrides, farm animals—this is the stuff of childhood memories (and laundry nightmares). Bella Organic also has kettle corn and a corn maze, perfect for kids who need to run off their snow-cone energy.
Tip: Call ahead to check what’s ripe, and bring cash—because explaining Venmo to a goat is complicated.
7. Enjoy the Oregon State Fair
- When: Aug 29–Sept 1, 10 AM–10 PM
- Where: Salem
- Cost: $8–12/adults, $6/kids 6–12, free under 6
From pig races to cow-milking demos, the fair has everything you didn’t know you needed. Carnival rides, cotton candy, and corn dogs make it a kid’s dream—and a dentist’s retirement plan.
Tip: Buy tickets online, check the schedule for puppet shows, and don’t let your child spot the giant stuffed unicorns unless you’re ready to play the ring toss 27 times.
Practical Tips
- Weather: 70s–80s, sunny. Sunscreen is your friend.
- Transportation: Public transit is stroller-friendly, but you’ll want a car for Salem and Canby.
- Crowds: Expect them. Bribery via snacks is recommended.
- Gear: Strollers, snacks, water bottles. Bonus points if you remember wipes.
- Closures: Everything is open, but double-check hours just in case.
Final Thoughts
Labor Day Weekend in Portland has it all—art, flowers, birds, animals, science, fruit, and pig races. Whether you’re chasing kids through a corn maze or convincing them that “no, you really can’t keep a penguin as a pet,” the long weekend is packed with family fun. Enjoy it—you’ve earned it.
Tiffany Wilson is a 42-year-old stay-at-home mom from Tigard, Oregon, raising three kids—Sophie, Noah, and Riley. She’s a warm, hands-on parent who mixes daily routines with creative fun, whether it’s a backyard scavenger hunt or building a blanket fort in the living room.