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2025 has already seen some big entrances and exits in Milwaukie. In February, the suburb just southeast of Portland said goodbye to Bob’s Red Mill Whole Grain’s store and restaurant, but welcomed pFriem’s tasting room and Keeper Coffee into the historic City Hall and firehouse building on Main Street in April after an extensive glow-up. The former mill town on the banks of the Willamette River, always more than the hometown of Dark Horse Comics, stays in the headlines with buzzy businesses and family offerings that hit every time.
Sip Twice As Nice
After walking through the front doors of Milwaukie’s former City Hall, customers face a decision: turn right into pFriem Family Brewers (10722 SE Main St., 971-465-6161, pfriembeer.com) or left into Keeper Coffee (503-891-5828, keepercoffee.com). There is no wrong choice. The first expansion of pFriem beyond its Hood River flagship location keeps the fresh IPAs it’s famous for flowing, along with a diverse tap list, including an imperial stout, a Japanese lager, and a doppelbock. Keeper bakes its pastries in house—the marionberry and cream galette ($7.75) is a top seller—and offers brunch until 3 pm.
Float Your Boat
Elk Rock Island is a fun and easy 13.6-acre natural area to explore. People hike on the trails, meditate on the rocks jutting out into the Willamette River, or in late summer, use the island as a launch point for splashing around in inflatable doughnuts. Also fun: ogling Dunthorpe’s riverfront mansions with private docks. Park at the Spring Park trailhead at Southeast 19th Avenue and Sparrow Street, and hike past the playground, through the forest, and across the 40-million-year-old land bridge to access the island.
To Market, To Market
We’re already in the thick of the season at Milwaukie Farmers Market (Southeast Main and Harrison streets, 503-407-0956, milwaukiefarmersmarket.com), which runs 9:30 am–2 pm every Sunday from May through October. In-the-know young families grab provisions from the market then walk to the playground at the Portland Waldorf School (2300 SE Harrison St., 503-654-2200, portlandwaldorf.org) with the enormous spider web climbing structure, and perhaps to the Ledding Library (10660 SE 21st Ave., 503-786-7580, milwaukieoregon.gov/library), which hosts extensive used book sales every weekend to coincide with the market.
Shop ‘til You Drop
The historical downtown of Milwaukie centers on Southeast Main Street. Favorite shops to poke around in include Good Measure Market (10999 SE Main St., 971-206-8905, goodmeasure-pdx.com) for sandwiches and Wine and Weenie Wednesdays; Things From Another World (10977 SE Main St., 503-652-2752, tfaw.com) to stock up on Dark Horse Comics made on the same street; and Enchanté Chocolatier (10883 SE Main St., 503-654-4846, enchantechocolatier.com) for housemade confections, yes, but also just for the smell of the chocolate and popcorn. Finally, the charming Spoke & Word Books (10863 SE Main St., 503-303-4680, spokeandwordbooks.com) opened in 2023 and now features a killer zine rack near the entrance with dozens of titles, many published by North Portland’s Microcosm Publishing.
Hear Here
Decibel Sound & Drink (11380 SE 21st Ave., 503-342-6764, decibel-pdx.com) is a stylish but comfortable bar that puts as much energy into the music and sound system as it does the craft cocktails. The owners get super nerdy about it—the website touts its large-format horn system with a JJ Electronic 323 as the house amplifier, if that means anything to you—but the average bargoer will just notice a great vibe and nicely curated playlist.