Searching for small-town charm just minutes from Portland? Head to Milwaukie! I’ve always loved how Milwaukie feels like a peaceful pocket right outside the city. Nestled along the Willamette River, it’s the kind of place where you can sip a locally brewed beer, take a walk through a riverside park, and hop on the MAX to downtown Portland—all in one afternoon. Whether you're looking for relaxed vibes or easy access to city life, Milwaukie makes a great base for exploring the region.
Best Time to Visit
For me, late spring through early fall is the sweet spot. From May to October, the weather is just right—mild, sunny days perfect for wandering the farmers market or catching a local festival. I’ve had some of my favorite riverside walks and outdoor meals during these months, and the town really comes to life without ever feeling crowded.
How to Get There
- By Car: I usually drive in along OR-99E—it’s a quick trip just south of Portland, and you can also get here easily from I-205 or I-5. It’s a nice drive with plenty of greenery along the way.
- By Light Rail: One of the things I love about Milwaukie is how connected it is. The MAX Orange Line gets you to downtown Portland in under 30 minutes—it’s a smooth, scenic ride and great if you’d rather skip parking downtown.
- By Air: If you’re flying in, Portland International Airport (PDX) is only about 25 minutes away. I’ve done that drive a few times, and it’s a breeze with rideshare or rental options.
Where to Stay
- Milwaukie Inn Portland South – I stayed here on a quick visit, and it was clean, comfortable, and super convenient if you’re traveling on a budget. It’s right off Highway 99E, so you can get around easily.
- Lakeshore Inn – If you don’t mind being a few minutes away in Lake Oswego, this inn is a lovely option. I loved waking up to waterfront views and being close enough to explore Milwaukie and the surrounding area.
- Airbnbs & Guesthouses – I’ve seen some great options in town, from cozy riverside cottages to modern lofts. If you want a local feel or a more private space, this is a great way to stay in Milwaukie like a resident.
Top Attractions
Shop Fresh and Local at the Milwaukie Farmers Market - Explore fresh produce, local crafts, and enjoy a lively community atmosphere.
Step Into the Past at the Milwaukie Museum - Discover local history and admire fascinating exhibits and artifacts.
Tour, Taste, and Stock Up at Bob’s Red Mill - Explore a working mill and savor wholesome, freshly ground grains.
Catch a Flick and Play Games at Wunderland Milwaukie Cinemas - Enjoy affordable movies and family-friendly arcade fun.
Browse Comics, Collectibles, and More at Things From Another World - Browse comic books, collectibles, and unique pop culture finds.
Grab a Classic Dog or Burger at Roake's - Savor classic hot dogs and fries in a nostalgic, casual setting.
Cruise Through for Shakes and Comfort Food at Mike’s Drive-In - Enjoy juicy burgers and creamy milkshakes at this retro eatery.
If You’re Hungry for Slow-Smoked Flavor, Feast at Buster’s Texas-Style Barbecue - Savor slow-smoked meats and enjoy bold, authentic barbecue flavors.
In Summary...
(and if you want to revisit my photo journey)- • Shop Fresh and Local at the Milwaukie Farmers Market
- • Step Into the Past at the Milwaukie Museum
- • Tour, Taste, and Stock Up at Bob’s Red Mill
- • Catch a Flick and Play Games at Wunderland Milwaukie Cinemas
- • Browse Comics, Collectibles, and More at Things From Another World
- • Grab a Classic Dog or Burger at Roake's
- • Cruise Through for Shakes and Comfort Food at Mike’s Drive-In
- • If You’re Hungry for Slow-Smoked Flavor, Feast at Buster’s Texas-Style Barbecue