In 2021, neighborhood historian Doug Decker, used pictures and maps to show the early days of Sullivan’s Gulch - both the neighborhood and and place itself. See the video, History of Sullivan's Gulch, at this the link.

Doug has now written up the information for a 4 part series on his website AlamedaHistory.org. He's included some new information and the old photographs and maps are available in higher resolution than on the video.  

Sullivan’s Gulch: A look back in four parts
(+ bonus)
Chapter 1: Homesteads and railroads
Chapter 2: Manufacturing comes to the Gulch
Chapter 3: Old Lloyd Golf Course + Shantytown
Chapter 4: The highway nobody wanted (coming)
Bonus: What’s a Gulch and where is it exactly?

The panoramic photograph above is of NE Portland in 1903.  It was taken just before the Sullivan's Gulch and Irvington were developed.  The view is east-northeast.    It's part of a bigger panorama of Portland taken by courtesy of local historian Doug Decker.

First a little orientation: 
​

• Point 1 is Rocky Butte
• Point 2 is on the Alameda Ridge, with just a few structures on it — probably farms
• Point 3. This open area is farm land that was on a trajectory to be part of the broader Irvinginton development, but not yet subdivided on the ground. Doug Decker says,  it's bordered by today’s NE Thompson-Fremont between 7th and 15th.  This may have been used by the Multnomah Fair Association for various activities.

A higher resolution version of the image, without the circles, can be found here.  Smaller images of the full panorama are here.

The earliest span over mid-Sullivan’s Gulch was the “28th Street Trestle.” Originally built by a streetcar company, the line continued from Couch, across the bridge and ended at Halsey, where the jog in the road is now.

https://alamedahistory.org/2025/03/12/earliest-span-over-mid-sullivans-gulch-the-28th-street-trestle/

https://www.oregonlive.com/hg/2025/01/a-forgotten-formula-determined-portlands-addresses-heres-how-it-works.html?gift=07172d17-f1c7-4bc6-9850-af81fd52228e

Excerpt from the article by Fran Gardner:
"Nearly every address in town was changed during the process known as the Great Renumbering, which was completed in 1933. Every house was given a set of black-and-white tiles with its new number. You can still find these on houses throughout the city.

The Great Renumbering was the time when the city instituted the “quadrant” system, with addresses assigned to Northwest, Northeast, Southeast or Southwest. Burnside Street and the Willamette River became the dividers.
A fifth quadrant, North, was added to take into account the bulge of land west of Northeast First Avenue, where the river meanders westward. The dividing line is Williams Avenue.
The Great Renumbering was a time when all the north-south streets became numbered avenues (except in North and a few enclaves, like Southeast Portland’s Ladd’s Addition)."

I’ve always wondered about the Irvington sign at 14th and Broadway and now I know - it really was a theater.