Let’s face it, everyone thinks Milwaukie is the least hip Portland suburb, but the myth doesn’t match up with reality. Okay, it’s true that the stretch along Southeast McLoughlin is a strip-mall nightmare. But Downtown Milwaukie is another story. Hop off SE McLoughlin before it gets ugly and meet with a host of eclectic little shops, surprisingly good restaurants and a killer farmer’s market. We’ve got three kid-friendly stops for you to make a day of it on Main Street in Milwaukie.

Farmer’s Market Fun
Start your exploration on a Sunday morning at the Milwaukie Farmer’s Market (10723 SE Main Street). It rivals any you’ll find in Portland proper with grass-fed this and organic-small-batch that. Bring your cloth grocery bags to avoid shifty looks from local merchants when you need to use a plastic bag. Think eco-friendly!

The market opens at 9:30 am and you’ll want to get there early to avoid a parking hassle — or take the bus, the market is just a block from the Milwaukie transit center.

If you arrive later, park by the Portland Waldorf School (2300 SE Harrison Street) and stop and play at the super awesome playground (or don’t let your kids see it!). Bring stroller so the little ones won’t get worn out walking a few blocks.

Your first stop at the market should be the face painting stand. The guy does some stellar cheek work for just $3. Sometimes there’s a line, but while you’re waiting you can snag a cup of local brew from St. John’s Coffee Roasters, and even grab a bag of beans to help you through the week to come.

Now grab a snack (so many to choose from: pastries, cheesecake, sausage, breakfast burritos, falafel and more) and snag a seat to listen to some terrific live music. It’s tradition for a gaggle of wobblers to assemble just in front of the band and dance. Your cheeks will hurt from smiling at them.

Once your groove has been thoroughly got on, you can make your way through the market buying items you may actually need, like tomatoes and carrots. Or get your holiday shopping out of the way insanely early, there’s plenty of handmade jewelry, pottery and original artwork to be had.

Chill Out
If it’s getting a bit hot, you can walk to the next block and head in to the air conditioned Main Street Collector’s Mall (10909 SE Main Street). Steer the young ones away from the glass cases and towards the soda fountain or to the rear of the store with its oodles of cheap collectible toys. The wall of plastic lunch boxes is particularly enchanting to the preschool set.

Last Stop
You’ll need to pry them away from the vintage My Little Ponies and Easy Bake Ovens eventually, because there is one more stop you don’t want to miss. French Chef Pascal Sauton (formerly of Carafe) has opened the best kept secret of this quiet little ‘burb: Milwaukie Kitchen & Wine. And yes, it’s kid friendly.

You may be stuffed from the farmer’s market, but don’t worry, the food here is phenomenal — and portable. There’s a sandwich menu, a number of deli items, and a well curated selection of high-end groceries and wine. More importantly, they sell handcrafted frozen entrees that you can bring home and throw in your freezer, to be used on those harried nights when you wish there was a super chill french dude around to cook you an awesome meal. Stock up and then head for home. Nap time awaits after your morning adventures.

Milwaukie Farmer’s Market
Every Sunday from 9:30 am to 2:00 pm
May – October
10723 SE Main Street
Milwaukie, Or 97222
Online: milwaukiefarmersmarket.com

Main Street Collector’s Mall and Soda Fountain
Open everyday from 10:00 am to 6:00 pm
10909 SE Main Street
Milwaukie, Or 97222
Online: mainstreetcollectorsmallandsodafountain.com

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Milwaukie Kitchen & Wine
Open everyday from 8:00 am to 6:00 pm
10610 SE Main Street
Milwaukie, Or 97222
Online: milwaukiekitchen.com

What are your favorite attractions in Milwaukie? Got a favorite spot that you want to share? Let us know in the comments below. 

— Sue Campbell