Tag Archives: MA

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.



Muffler Man sketch by Chandler O'Leary

Kings of the road

Well, if I’m going to spend all this time talking about roadside attractions, I would be remiss if I didn’t include the legendary Muffler Men—guardians of gas stations, presidents of photo ops. If you’ve ever taken a road trip, you’ve probably seen at least one of these guys along the way.

These behemoths started appearing in the early 1960s (the very first one was on Route 66), to promote the brand new International Fiberglass Company in California. For whatever reason, they usually ended up in front of gas stations, holding giant mufflers—hence the nickname.

Muffler Man sketch by Chandler O'Leary

By 1970 there were thousands of them around the country, but the 1973 oil crisis forced the decline and eventual demise of International Fiberglass. These days the muffler men are an endangered species, down to just a few hundred stalwart lads (and a handful of lasses, too!).

Saloon Cowboy (Muffler Man) sketch by Chandler O'Leary

For me, finding them has turned into something of a quest—and not just because I’m a completist (though, of course I am). You see, the most fun thing about these guys is that they’re not identical—there are many, many variations on the original design (and a few knock-offs, to boot).

Paul Bunyan Muffler Man sketch by Chandler O'Leary

Probably the most common variation is the Paul Bunyan—they’re certainly the most recognizable, even when their axes get stolen.

Paul Bunyan Muffler Man sketch by Chandler O'Leary

And when they’re spiffed up to their original glory, they’re unmistakeable. (This one is a mobile muffler man! When he surprised me at the local Daffodil Parade a few years ago, it felt like Christmas had come early.)

Carpet Viking sketch by Chandler O'Leary

Though I’ll never pass up any iteration of Paul Bunyan, I’m most excited about the rare, extreme variants, the roadside sideshow—the Uniroyal Gals, the Happy Halfwits, the Carpet Vikings.

Harvey the Rabbit (Muffler Man) sketch by Chandler O'Leary

And best of all are the mutant modifications that have happened to some of these guys (you should have heard me squeal when I found this one!). Some have been altered so much as to be rendered almost unrecognizable. But you can’t fool me—once a muffler man, always a muffler man.

So tell me: have you found any muffler men in your travels? Do you have one in your neighborhood? I’m always on the look-out for a good one, so if you have any recommendations, I’m all (rabbit) ears.




Modern Pastry sketch by Chandler O'Leary

Holy cannoli

If you want the best cannoli it’s possible to get outside of Italy, you really can’t go wrong in Boston’s North End—there are plenty of places that will deliver the goods (special shout-out to Maria’s!). Probably the most famous are Modern Pastry and it’s rival, Mike’s. I’ve visited both many times over the years, and you know? They’re both wonderful. (Mike’s is especially good if you want something other than a cannoli, for a change—lots and lots of choices there.) To me it’s not worth it to go into the finer points of which ricotta is slightly sweeter, which shell is heavier, etc. Either way, I’m not complaining.

But hey—I’m an illustrator, not a food critic. If it’s going to take something extra to make me choose between two fabulous pasticcerie, I’m goin’ with the place with the best neon sign.

Just sayin’.

Boston sketch by Chandler O'Leary

Boston Strong

I wasn’t there at the time of the Marathon bombings last year—I was here, on the opposite coast. But Boston is my home city, and I remember feeling at the time that I had to do something, no matter how small. So I grabbed the first thing I always think of—my sketchbook—and put together this little tribute while I waited anxiously for news with the rest of the country.

A year later, I’m still far from the scene, but you can bet I’ll be cheering for the marathon runners this year, and for my favorite city. Stay strong, Boston.

Hilltop Steakhouse sketch by Chandler O'Leary

The last roundup

I couldn’t be here in person for this, and I haven’t actually eaten here since I was a kid. But Giuffrida’s has been a familiar (and completely incongruous) landmark on countless drives north of Boston over the years, and this is the first neon sign I ever loved. So when my dad told me it was closing after over fifty years, I dug out a blurry old photograph I had, and whipped up this sketch. It’s not the same as sketching the real thing, but I’m sorry to say it’s too late for that now. Apparently even the shiny fiberglass cows have been rounded up and carted off.

I have no idea what on earth a giant neon saguaro cactus and a ranch-themed restaurant was doing just ten miles from Bunker Hill. But I’m so glad it was there to be one of the first points of interest on my mental map.

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

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 on the T has hardly changed at all.

As we approached the city, I glanced at the system map to decide where to go first. As I read, the name of each stop triggered a flood of memories and images, all arranged by the cardinal directions, rather than by the years. This is probably why I love maps so much. Not only do they describe and organize a particular place—they also catalogue my entire relationship to that place. For unfamiliar cities, I love watching my mental map grow from a blank slate to a rough sketch and beyond. For places like Boston, the grid in my head is chock-a-block with minute, accurate (though sometimes obsolete) details, annotated pictures and pinned moments in time.

How about you? Do you have a place where your memories unfold like a treasure map? Or somewhere you know so well that every subway stop tells a personal story?

Boston T map sketch by Chandler O'Leary