How long would it take to walk every street in Oakland?
How many streets does Oakland have?
Oakland has 36 km of walkable streets and paths, across 30 named streets. Walking 5 km a day, it would take at least 8 days (about 1 week) to walk every one of them.
Covers the area inside the official Oakland boundary on OpenStreetMap, not the rest of Chicago. Last updated 5 October 2026.
Every street walked once, 5 km a day. Real walks double back, so the true number is a little higher.
Oakland is the 75th biggest of Chicago’s 77 community areas by length of streets. A lot of it is for walking only: 36% is paths, footways and steps, against 19% in a typical city. Along the way there are 3 landmarks to collect as stamps.
Oakland is part of Chicago: 2,453 days for the whole city.
Your pace
The same streets at a different speed.
What’s the longest street in Oakland?
1.8 km inside Oakland
1.4 km, then South Drexel Boulevard at 1.4 km
Park paths, footways and steps, all walkable
Landmarks to collect
3 stamps in Oakland. Each one is added to your map when you walk past.
Put it in perspective
Questions
What counts as a street?
Every street, lane and path in OpenStreetMap that you’re allowed to walk on, named or not: residential streets, main roads, footways, park paths and steps. Motorways, private roads, driveways and car parks are left out, and so are pavements drawn as separate lines, because walking one already counts for the street beside it.
Why “at least”?
The number assumes you walk each street once, with no doubling back and no walk to get there. Real walks overlap, so it will take a little longer.
Where does the data come from?
From OpenStreetMap, a map of the world made by volunteers. Oakland’s streets were last updated in October 2026.
What if a street is missing?
Anyone can add it to OpenStreetMap. It will appear here, and on your map in Untrod, after the next update.
How does Untrod track it?
Untrod for iPhone records your location during a walk, and only then, and colours in each street you walk along. Your map is only visible to you until you choose to share it.
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<p style="margin:4px 0 0;font:13px/1.4 sans-serif"><a href="https://untrod.app/streets/chicago/oakland">8 days to walk every street in Oakland</a> · Untrod</p>
