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How long would it take to walk every street in Woodlawn?

At least
25days
walking 5 km a day·about 4 weeks
Start colouring in Woodlawn
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Street map of Woodlawn

How many streets does Woodlawn have?

Woodlawn has 124 km of walkable streets and paths, across 58 named streets. Walking 5 km a day, it would take at least 25 days (about 4 weeks) to walk every one of them.

Covers the area inside the official Woodlawn boundary on OpenStreetMap, not the rest of Chicago. Last updated 5 October 2026.

124km of streets
58named streets
9landmark stamps to collect

Every street walked once, 5 km a day. Real walks double back, so the true number is a little higher.

Woodlawn is the 50th biggest of Chicago’s 77 community areas by length of streets. About 22% of it is paths, footways and steps, close to the 19% of a typical city. Along the way there are 9 landmarks to collect as stamps.

Your pace

The same streets at a different speed.

25days
at 5 km a day · about 4 weeks
1 km a day15 km a day
30 min a dayabout 2.5 km50 days
1 hour a dayabout 5 km25 days
2 hours a dayabout 10 km13 days
Weekends only2 hours each day7 weeks

What’s the longest street in Woodlawn?

Longest streetEast 67th Street

2.7 km inside Woodlawn

Next longestSouth Stony Island Avenue

2.6 km, then East 63rd Street at 2.5 km

Paths and footways28 km

Park paths, footways and steps, all walkable

Street mix
Residential streets 60%74 km
Paths and footways 22%28 km
Main roads 18%22 km

Landmarks to collect

9 stamps in Woodlawn. Each one is added to your map when you walk past.

4churches
2historic buildings
1park
1museum
Cosmopolitan Church Of PrayerChurch
Midway StudiosHistoric building
Jackson ParkPark

Put it in perspective

About 3 marathons
Roughly 161,000.0 steps
About 1% of the way around the Earth

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. Woodlawn’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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<iframe src="https://untrod.app/embed/chicago-9884779?theme=light" width="400" height="220" style="border:0" title="25 days to walk every street in Woodlawn"></iframe> <p style="margin:4px 0 0;font:13px/1.4 sans-serif"><a href="https://untrod.app/streets/chicago/woodlawn">25 days to walk every street in Woodlawn</a> · Untrod</p>