In 1845 a man named Andrew Fellows, the first to have a permanent residence in the area we know as Milwaukie today, builds a small cabin approximately at the site of today's intersection of McLoughlin and Jefferson. Two years later a man named Lot Whitcomb, a pioneering entrepreneur, arrives and takes over Fellows' abandoned cabin. Around the same time, the Luelling (later spelled Lewelling) family also settled in the area, bringing all of their knowledge of how to cultivate orchards. Fellows disappeared, but both Whitcomb and the Luelling family went on to shape the early history of Milwaukie.
Lot Whitcomb formally claimed Milwaukie in 1848. He named it after the city in Wisconsin–his home state–because he admired the city and the meaning of the name, "gathering place [by the water]," derived from the Algonquin language. Situated at the confluence of the Willamette River, Cold Creek, and Kellogg Creek (now Kellogg Lake), Milwaukie was poised to become a major player in commerce on the Willamette River.
Whitcomb, along with William Torrance and Joseph Kellogg plated Milwaukie in 1849. As the population grew to 500 inhabitants, a post office opened (with Mr. Whitcomb as postmaster), and Hector Campbell (an educator who opened Milwaukie's first school) was elected to represent Clackamas County in the first session of the Oregon Territorial Legislature held at Oregon City.
In 1849 Whitcomb developed a steamship manufacturing company along the Willamette that thrived in the following years because of the California Gold Rush. The ships provided a mechanism for delivering regional timber and white flour from Milwaukie's Old Standard Mill to California's Bay Area. By the 1850's growth and opportunity in Milwaukie was beginning to outpace that of Oregon City.
The first public transportation between Milwaukie and Portland was a steam-powered ferry from the foot of Jefferson Street on Milwaukie Bay to the south end of Macadam Ave in Portland. As Portland's harbor became larger and more available, Milwaukie became less attractive for sea-going commerce. Businesses dependent on river hauling suffered as the economy moved away from river life; the Old Standard Mill went out of business in 1879.
Over the decades the Luelling/Lewelling family had been hard at work in their orchards; they established the first fruit tree nursery in the Western U.S. In 1878 they founded the ever popular Bing Cherry variety. Members of the family went on to contribute to the town and the state, opening Milwaukie's city library in 1889, and spearheading efforts of Oregon's populist movement.
The town's population growth slowed along with the decline of river industry as it was challenging to reach except by boat. In 1892 things changed when the East Side Railway connected Oregon City to Portland via Milwaukie with an electric interurban streetcar. By 1900 there was talk of the town becoming a suburb of Portland because of its dwindling residents, but by 1903 the City of Milwaukie had incorporated and began to grow again.
New industries cropped up like the hand-forged tool manufacturer P&C Tools, a staple in Milwaukie from 1920 through 1990. The development of both the "Superhighway" (Hwy 99E) in 1937 lead to suburban development after the Second World War, and the 1969 Milwaukie Expressway (Hwy 224) improved the city's connection on Portland and highways to the east. The most recent transit expansion was the addition of the Max Orange Line between Milwaukie and Portland.
The success of challenger comic company Dark Horse Comics, founded in 1986, helped put Milwaukie and greater Portland on the comic industry map. Founder Mike Richardson decided to publish comics aimed at a more mature audience and to offer comic creators full ownership of their material–a radical shift in the comic industry. Since the 1990s, Dark Horse has held strong as the number three publisher in comics behind Marvel and DC.
There are two elementary schools in Milwaukie, Milwaukie Elementary and El Puente Bilingual Elementary School. Rowe Middle School is in the adjacent neighborhood, Lake Road. Milwaukie High is the local high school and Milwaukie Academy of Arts–a free charter school focused on visual and performing arts–is embedded in the Milwaukie High campus.
Milwaukie Riverfront Park is a beautiful, aptly named park along the east bank of the Willamette River. Situated directly across Hwy 99E from Milwaukie's downtown, the park provides residents with easy access to one of the neighborhood's greatest assets: river views. The 8.5-acre site boasts a new boat ramp, riverfront walking trails, and restroom facilities.
Dogwood Park located just off Main Street in downtown is a small but lovely park to enjoy an unobstructed view of Kellogg Creek and enjoy a picnic lunch.
Milwaukie is another great neighborhood to explore on foot as most retail shops, eateries, and point of interest are nestled right in the middle of downtown. If you're looking for a light start to your day, head to Rohst cafe, a relatively new addition to the business district just north of the Max station on SE 21st, for a warm beverage and a pastry. Heartier breakfast fare is on SE 21st a few blocks north at Sully's Cafe, a family-owned neighborhood favorite since 2000.
If you're ready for shopping and browsing at this point, walk a block over to SE Main Street and visit Things from Another World for graphic novels, toys, and comics curated by the founders of the legendary Dark Horse Comics. Just down the block is Revolve Vintage with a selection of modern, contemporary, and mid-century home furnishings. The ultimate retail exploration might be the Main Street Collector's Mall & Soda Fountain with over 60 dealers offering collectibles, antiques, memorabilia, jewelry, and furniture. Stop at the soda fountain for a milkshake, float, sundae, or soda. Stretch your legs after snacking by walking over to SE 21st and south a couple of blocks to Molly Muriel Apothecary for ethically and locally made soaps, candles, and essential oils.
Take advantage of downtown Milwaukie's activities, set up an appointment to try your hand at archery at Broken Arrow Archery, on SE Adams between SE Main and SE 21st Streets, where they welcome beginning and seasoned archers. Grab lunch at nearby Milwaukie Station (also the Max station) with a smattering of food carts including Filipina Cuisine, Thai Street, and Le Tap, all conveniently close to Dogwood Park.
Head back up SE Main to the corner of SE Jefferson to the Wunderland Theater where you can catch a movie or play arcade games. Get some fresh air after the movie with an afternoon stroll through the Riverfront Park on Milwaukie Bay. You can catch a small section of the 6.2-mile Trolley Trail that runs from Portland to Oregon City that cuts through the park or explore on one of the park’s other riverside trails.