Category: Planes & Trains

DetourLake Shore Drive, Chicago, IL

Chicago sketch by Chandler O'Leary

For as disorienting as being awoken before dawn by owls can be, it’s nothing compared to how it feels when you suddenly find yourself on the opposite end of the country than you planned to be. When you’re expecting to land in Houston, and what you get is a hurricane in your path, a sudden… More

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T-timeBoston, MA

Boston commuter train sketch by Chandler O'Leary

Twice in my life (about 15 years apart) I’ve lived within an hour of Boston; and a couple of years ago I got to show the Tailor around my old stomping grounds. The city’s undergone a lot of transformations in recent years (Big Dig, I’m looking at you), but I love that the trip in… More

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Dusky deltaPuget Sound and Nisqually River Delta, WA

Nisqually River Delta sketch by Chandler O'Leary

As much as I love road trips, my hands-down favorite way to get between Tacoma, WA and Portland, OR is by train. Especially along the Puget Sound—where the tracks run literally inches from the shore—the views are absolutely gobsmacking. On this day, I was lucky enough to have a flawlessly sunny afternoon (in April that’s… More

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