Those nice sweeping bends leading north from Knott Street between NE 29th and 31st in the Alameda neighborhood are not there by accident: they were put there on purpose to solve a very specific problem.
But there was a slow-moving accident that made them necessary and it involved bad the absence of planning, perhaps a measure of greed and too little communication, plus the passage of time. Figuring out this back story has been a bit of a puzzle, which is fine because it represented an historic puzzle on a scale never attempted back in the day, more than 100 years ago.
You know the bends we’re talking about. Take a look:

Google Earth image showing the area bounded by Siskiyou, 29th, 33rd and Knott which posed major challenges to developers in the 19-teens until the city came up with a simple idea but hard-to-achieve plan. Toward the bottom of the photo, note the curved streets leading north off Knott at NE 29th, NE 30th and NE 31st.
Understanding Plats and Subdivisions
To understand what happened here, it helps to know about plats and subdivisions, which are different than actual neighborhood names. Portland is made up of more than 900 plats. A plat is a localized engineering plan and legal survey for development of a subdivision that shows the precise location of streets and lots. Back in the day developers gave these plats names that would catch a prospective home buyer’s eye, or that meant something to the developer.
Today’s Alameda neighborhood, for instance, is made up of 23 separate plats, all filed at different times by different developers who were competing with each other and speculating on market conditions when they bought chunks of what had been old homesteads and farms claimed in the 1850s and 1860s. There was indeed an Alameda Park plat (filed in 1909 by the Alameda Land Company), but it’s only one piece of what the City of Portland today refers to as the Alameda neighborhood. 22 other subdivision plats—with names now lost to time except on property legal descriptions—make up today’s neighborhood.
Here in today’s Alameda we’re made up of the following plats: Alameda Park, Olmsted Park, Meadow Park, Linlithgow Park, Homedale, Irvington, Irvingdale, Irvingwood, Edgemont, Charleston’s Addition, Pearson’s Addition, Stanton Street Addition, Hudson’s Addition, Gile Addition, Town of Wayne, Town of Wayne Replat, Quinn’s addition to Town of Wayne, Waynewood, Dunsmeade, Hillside, George Place, Bowering Donation Land Claim Tract, Norton’s Subdivision, and Gleneyrie. Phew. All filed by different owners/developers with the county surveyor in the 40 years between 1882-1922.
Remembering the deep history of these lands
Going back in time, it’s important to remember that before these lands were claimed as homesteads by the first white Euro-American arrivals, the federal government forcibly dispossessed the area’s indigenous people from these lands. All of us in the Portland area live today on lands ceded to the U.S. by Chinookan tribes and bands; their former home lands since time immemorial. Read more about this deep history here.
This area was part of the City of East Portland until 1891
The east side wasn’t actually Portland until after 1891, it was East Portland, a separate city. Prior to that, we were three separate cities sharing some limited common infrastructure, but with different character and focus: Portland (on the west side of the river), East Portland and Albina.
In 1891—in an attempt to roll together the greater Portland area population into one number that would intimidate rival Seattle which was growing fast—the three towns consolidated into one (46,385 people in Portland + 10,000 people in East Portland + 5,000 people in Albina = 61,385 people total in the Portland “metropolitan” area). Take that, Seattle (total 1890 population: 42,837).
There had been a boomlet of development about the time the transcontinental railroad arrived in Portland in the spring of 1882, when some plats were filed in East Portland including “The Town of Wayne” plat in the heart of today’s Alameda. After the Lewis and Clark Centennial Exposition in 1905, which put Portland on the map, a bunch more plats were filed, and then again during the 1920s, after the pandemic.
But let’s get back to the bends.
Too many disconnected plats – a real estate collision
Think of this accident of time as a kind of real estate development collision. The helter-skelter nature of platting before we became part of Portland—fueled in part by spikes in the real estate market which drove owners to create small, disconnected parcels on paper that were never actually developed—resulted in plats with different types of street and lot layouts. As larger, newer and better-planned subdivisions spread out to divide up more territory, the patchwork northwest corner of 33rd and Knott became a vortex of confusion. The city coined a perfect term for it at the time: misfit platting.
Some plats had alleys, some didn’t. Some had many narrow lots. Some had fewer larger lots. There was only one through street and it had varying widths. Corners didn’t line up. There was no street naming protocol. In short, it was a mess.
But the area was still just multiple hopeful plans on paper—these were open fields well into the late 19-teens, even though more than 45 owners had already bought in—and people continued buying, holding and even trading lots as a speculative investment. Here’s what it looked like by about 1915:

This diagram from the Oregon Journal on May 20, 1918 shows the jumble of plats that used to occupy the area bounded today by NE Siskiyou on the north, Knott on the south, 33rd on the east and 29th on the west. The plats include: Town of Wayne, (1882); Quinn’s Addition to the Town of Wayne, (1886); Hudson’s Addition, (1892); Fairview Addition, (1889); Meadow Park (1890); and Charleston’s Addition, (1895). A careful examination shows that each plat is organized differently. Note that the Fairview Addition even had alleys.
In the early 1910s, with construction and sales well underway in nearby Irvington, Alameda, Beaumont and Rose City Park, developers turned to the next nearby open lands in the pipeline for development and found this total mess.
There was only one real solution that came to mind: Go back to the drawing board and replat the whole area, something never done on this scale (and perhaps never since). But how you do that with specific lots already owned by dozens of hopeful investors in planned subdivisions that had been legally filed and on the books for as long as 30 years?
You see the problem now.
It first surfaced in the newspaper in February 1915:

From The Oregonian, February 12, 1915
The problem percolated among the property owners and the city engineering office for a while until they developed an ambitious plan about how to proceed:

From the Oregon Journal, June 20, 1915
Fisher’s meeting with the property owners went well and all but one got on board. A petition was signed a few months later to send a message of good faith to the city. The last line of the article summed up the problem nicely: the addition is said to be a perfect labyrinth.

From the Oregon Journal, January 9, 1916
The city engineers worked with the Title and Trust Company to do the necessary temporary title transfers to a holding trust that would allow a clean slate and then started drawing different lines, keeping everyone whole, eliminating the labyrinth, adding those curves, and retitling every single lot back out of the temporary trust. The result was a brand-new subdivision called Waynewood, a tip of the hat we suppose to the old Town of Wayne plat and the Irvingwood subdivision just to the north.

The official plat of Waynewood filed with the Multnomah County Surveyor on February 2, 1918 containing the brand-new retitled lots and redrawn streets. In addition to understanding how the curves came to be, the replatting process also explains the misaligned corner at NE 29th and Siskiyou.
A story in the Oregon Journal on May 30, 1920 explained the process and the benefits:
Today all of the energy and consternation that went into that process is completely invisible to us here in their imagined future (at least until now), our only clues the graceful curved streets that lead north from Knott Street. Those curves are reflected south of Knott as well, but they came later when the subdivision known as Dolph Park was platted in 1924, and that’s another story.
If you like neighborhood history puzzles like this as much as we do, check out the Prescott Jog, the Ainsworth Long Block, the Ghost of Crane Street and remembering Laura Hamblet.