Courtesy of Hamid Shibata Bennett 

The charming town of Milwaukie, less than a 10-minute drive from southeast Portland’s Sellwood-Moreland neighborhood, is an ideal location for families looking for more space, lower home prices, a quaint downtown, and the proximity of Portland, without being directly in the city. 

What is now known as Milwaukie was home to the Clackamas Indians. (Fur traders, missionaries and settlers would later introduce deadly diseases that decimated the Clackamas population.) In 1847, settler Lot Whitcomb established the area’s first post-contact settlement, naming it after his hometown of Milwaukee, Wisconsin. At the time, the Midwestern town was often misspelled, hence the “ie” spelling variation here.

What Neighbors Say

Courtesy of Deana Tennant

Deana Andersen-Tennant grew up in Milwaukie, so when she and her husband of 25 years, Randy Tennant, were starting a family, they knew that’s where they wanted to live. Deana and Randy bought their home in 2001 and have lived in the area since. The two have four children: Alex, age 25, Cooper, age 21 and twins Asher and Janelle, age 11. 

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“While Milwaukie is growing, it continues to hold on to its small town appeal of local parades, such as the Umbrella Parade and the tree lighting festival,” says Deana. “It has a weekly farmers market that runs May through October, a beautiful waterfront park that encourages family usage … and plans for a new children’s play area.”

The family sees new releases and plays arcade games at the Milwaukie Cinema, which also includes Electric Castle’s Wunderland arcade. “It’s the same theater I grew up going to,” says Deana.

She says the only downside of living in Milwaukie is that the town has gone from being relatively unknown, to skyrocketing to one of the most sought-after communities in the Portland area (which has also increased home prices). “But the majority of changes to Milwaukie since we moved here have all been positive, especially the influx of new families that have helped grow Milwaukie into a more culturally diverse community.”

Eat Here

Courtesy of Bob’s Red Mill

The red building of Bob’s Red Mill, visible from the Milwaukie Expressway, is an iconic landmark of the city. And while the employee-owned mill is best known for its variety of flours and mixes, the Bob’s Red Mill Whole Grain Store, Restaurant & Bakery is a great, family-friendly restaurant. The restaurant serves breakfast all day, so it’s the perfect place for families who can eat pancakes, omelets and hash browns any time of day. But the restaurant also has hot and cold sandwiches, grain bowls and salads, plus seasonal pastries, cookies and more fresh from the bakery.

Generations of Milwaukie kids have celebrated birthdays with pies and arcade games at Pietro’s Pizza. Neighbors hankering for a classic hamburger, crispy fries (or tots) and silky milkshakes know that Mike’s Drive-In is the place to go. For choose-your-own dining, visit the Milwaukie Station Food Cart Pod in downtown Milwaukie. There you’ll find Thai, gyros, sandwiches, BBQ, fried chicken and more. Grown-ups needing their daily caffeine fix head to the homey Milwaukie Cafe and Bottle Shop for coffee and lattes. The whole family will love the cafe’s house-made biscuits, breakfast sandwiches and baked goods. Another bonus: You can pick up a bottle of wine here, too. 

Play Here

Courtesy of North Clackamas Parks and Recreation District

Neighbors say one of the best perks about living in Milwaukie is the easy access along the Willamette River. For walking paths, waterfront vistas, a boat ramp for fishing and more, families flock to Milwaukie Bay Park; the equally scenic Kellogg Creek Park is also nearby. And for those who want to get in some exercise while outdoors, there’s the 6-mile Trolley Trail. This multi-use trail is a mix of paved and gravel pathways, great for those walking, strolling or rolling. 

For old-fashioned family fun indoors, neighbors head to Milwaukie Bowl to knock down some pins. First opened in 1957, the bowling alley has retained much of its mid-century character, including 16 wood lanes, beer on tap, and pizza and soda for the kiddos. And for avid bowlers, there’s youth and adult leagues. For families looking to make a splash, there’s the North Clackamas Aquatic Center (pictured above). The waterpark has swimming pools, a wave pool, water slides and a 29-foot-tall rock climbing wall. For littles, there’s an interactive kiddie pool; and adults can relax in the hot tub. 

Live Here

Courtesy of Walk Score

$499,900: Median home price

$2,280: Median rent for a 2-bedroom apartment

To read about more fun neighborhoods like this one, check out the rest of our Neighborhood Guide.

Tiffany Hill
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