Spend the Whole Day in Woodstock With the Family

The Woodstock neighborhood is a charming, walkable area with many of its amenities right on Woodstock Boulevard. It’s easy to spend a whole day here with your kiddo, both having fun and getting things done. Even better: Take public transit, or park your car along this bustling street and you and the family can explore the area all on foot! Read on for top spots in the area.

Stop No. 1: Kids Castle Cuts

Book an appointment here beforehand and make haircut day a fun day. This family-friendly and COVID-cautious hair salon, tucked away under Laughing Planet, has TVs with shows for kids of all ages (adults can get cuts too), fun barber seats for toddlers, plus other tricks to keep them happy and facing the right way during the cut. Kids get a balloon and tattoos when they’re done. Pro tip: This salon is also a repeat PDX Parent Reader Favorites Top 5 winner.

Stop No. 2: Musical Monsters & Budding Bookworms

Just across Woodstock from Kids Castle Cuts is a great little bookstore that also offers kids music classes. Find books appropriate for youth of all ages: graphic novels, board books, picture books, middle readers and young adults. The shop’s closed during class time but you can always come back after lunch or check their class calendar beforehand if you’re a Type A planner (respect).

Stop No. 3: The Heist

Find something for everyone at this newish food cart pod in a renovated bank building with plentiful indoor and outdoor seating, highchairs included. They’ve also got several activity easter eggs for kids to enjoy: a bank vault, a fish tank, a stack of board games and a whole room of pinball with a couple of step stools to help littler ones reach. Pro tip: If you need a quieter option with a little less to explore, try Laughing Planet, just above Kids Castle Cuts — they’ve got dinosaur toys and a menu that’s both kid-friendly and healthy.

Stop No. 4: Piccolina

This family-run children’s resale boutique has great stuff with the cutest mushroom décor. Stop in if you’re in need of any gently used gear, clothes, shoes or toys. Pro Tip: Make an appointment to consign a bag of items in good condition that your kiddo’s outgrown for cash or store credit.

Stop No. 5: Woodstock Park

This park is not on Woodstock Boulevard — the entrance is on SE 47th and Steele Street — but there may come a time of day when restless little legs require more range. In that case, journey five blocks north of the library and find a grassy expanse (dogs will find happiness here, too) with play structures including swings, teeter totters and a slide.

Bonus Stop No. 1: Heart Coffee + Thrifting

If your kiddo is a stroller-aged child, they may fall asleep in there. This is what we call “me time.” Get a perfect latte at Heart Coffee and peruse the racks at Goodwill or Red Fox Vintage. And if your kiddo is older, and enjoys the thrill of the hunt, these stops will be fun for them, too. Pro Tip: Bring unwanted items you’ve uncovered during spring cleaning to the drive-up donation site at Goodwill. 

Looking for another family-friendly neighborhood itinerary? We got you! Head to Foster Powell for some tasty bagels, new games and toys, a scoop of ice cream and more.