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Seattle is sandwiched between two bodies of water east and west: Elliott Bay and Lake Washington. But only one road draws a direct path between saltwater and freshwater — Madison Street.

That curiosity about the layout of Seattle streets recently sent me on a mad sketch-walk exploration of Madison Street. I say mad not just for the pun: There’s really a maddening amount of interesting stuff to see along this route.

The four-mile stretch stitches together an eclectic cross-section of the city including downtown, First Hill, Capitol Hill, the Central District and Madison Valley. Not every building along the way is as eye-catching as the old Federal Building on First Avenue (below), but each neighborhood I walked by offered more to see and sketch than I could possibly fit over several walks.

To understand the genesis of this important thoroughfare, you have to imagine the forest that was most of Seattle back in the 1850s, when the first European settlers began to arrive.

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Seattle Times news artist Gabriel Campanario has been capturing Seattle's places and people in hand-drawn sketches for more than a decade. To see past columns, visit the Seattle Sketcher home page. Prints, notecards and a book of Campanario’s sketches are available for sale through The Seattle Times store. You may also fill out an illustration request to order a specific image.

While modern Seattle was taking shape around Pioneer Square and the Elliott Bay waterfront in the early 1860s, a judge named John J. McGilvra purchased 420 acres on what we know today as Madison Park. The judge then apparently took it upon himself to cut a road through the forest at his own expense to connect his remote property with Seattle’s emerging downtown. He started a daily stagecoach service, rented out cottages and Madison Park soon became a summertime destination. You could call McGilvra one of Seattle’s first developers.

Why no other streets were plotted to link Elliott Bay and Lake Washington remains unclear to me. Maybe Madison, named after U.S. President James Madison, was enough. By the early 1900s it had become an important city corridor. Cable cars ran up and down the steep hills and a cross-lake ferry operated from Madison Park to what would later become Kirkland. (Years ago I sketched guys with metal detectors looking for old jewelry or coins that ferry passengers might have dropped there back in the day.)

More than 100 years later, the pace of change along Madison Street seems to be speeding up again. From Capitol Hill to the Central District, a denser city of bulky residential complexes is taking shape. In Madison Valley, neighbors have recently been fighting a development that is going to displace a beloved gardening store.

Now that summertime is in full swing, an urban hike along Madison gives you a front-row seat to all those changes, not to mention a good dose of exercise!

If you’d like to try it in one go, I recommend setting aside at least three or four hours for the full walk. Start at the Ivar Haglund statue on Alaskan Way early in the morning and you could be at the small-business district on the Lake Washington shoreline in time for lunch. Then a ride on Metro bus 11 will get you back downtown.

Above you have a map and sketches of locations that caught my eye. I can’t wait to find out what parts of Madison may draw your attention.

The old Federal Building at First Avenue and Madison Street.
The old Federal Building at First Avenue and Madison Street.