Tag Archives: North End

Boston sketch by Chandler O'Leary

One if by land, two if by ice

Even though New England was the heart of the original thirteen colonies, in my experience you’re more likely to find this type of flag flying here than this one. For me there’s no real surprise here: Boston is a city that takes its sports seriously, and the Bruins flag is as much a symbol of Beantown as the Old North Church. I can certainly relate—New Englanders are my people and hockey my sport, but even beyond that, I know what it’s like for a winning goal to feel something like a religious experience.

Bruins Madonna sketch by Chandler O'Leary

Don’t believe me? Ask Our Lady of the Slapshot here.

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Boston colonial cemetery sketch by Chandler O'Leary

I see dead people

Okay, you’re going to think I’m a total weirdo for getting so excited over bunch of headstones (and I have many, many more sketches than these…), but since it’s Halloween this week, I figured I could get away with it. I have to tell you, I have a serious, major thing for colonial graveyards. My grandfather loved them, too. As a lifelong, dyed-in-the-wool New England Yankee, he knew where all the good ones were. I used to take the train up from Providence and then drive him around three states (uh, about a thirty mile radius, ’round those parts…) in his car, while he showed me all the best, oldest, and weirdest headstones he could remember, in every little town and village. If you want a whole colony’s worth of specimens in one place, though, you can’t beat Boston. My two favorite burial grounds there are like little cities, in and of themselves.

But I’m not into 300-year-old headstones for any normal reason, like colonial history or possible genealogical discoveries (though I’m not knockin’ that stuff). I love them because they’re literally monuments to early graphic design. Great typography? Check. Graphic symbolism? Heck, yeah. Amazingly inventive, refined and creepy illustration? In spades.

(Sorry. I can’t resist a grave-digging pun—not this close to Halloween.)

Boston colonial cemetery sketch by Chandler O'Leary