Boston | A Day of Beacon Hill, John Hodgman, and Vacationland

Iconic Acorn Street, and nearly just as iconic dog, in Beacon Hill

Forgive me in advance if I overly gush, become melodramatic, or fan-out. Trust me, this will be weird for me too. Living in Park City, Utah for a few years, I routinely ran into celebrities at Sundance or on their ski vacations. And I never approached them; not even when I was seated only a couple feet from Tracey Ullman at an exclusive, Norwegian restaurant. It didn't occur to me to burden her with my anecdotes of breaking bedtime every Sunday night, as a little girl, to watch her on tv. That would have been undignified and possibly awkward (obviously, I spent a past life in Victorian England amongst the etiquette-obsessed elite). And when I was only inches from Conan O'Brien - a teenage crush - backstage at his tv show in New York? No, didn't open my mouth then either. But dignity and Victorian sensibilities be damned, I'm going to gush a little over John Hodgman! Not only is he one of my favorite funny people and, yes, I'll say it, my favorite Yalie, but he's also a New Englander. Due to the misfortune of my birth in California, I'll always be considered "from away." No matter how many years I live here, I cannot be called a New Englander. Hodgman, however, gets to claim native status. Something my weird, little heart envies. He's a child of the Commonwealth, raised in Brookline, Massachusetts, and I recently had the pleasure of seeing him perform his new, comedy show, Vacationland, in Boston.

First of all, have you heard of the Judge John Hodgman podcast? I listen to a lot of podcasts, and his remains my favorite. He's witty and quick, and though the disputes on his show are low stakes (e.g., the time one spouse attempted to temporarily ban her spouse from wearing crocs), there's a natural storyteller quality to Hodgman's presentation that is utterly charming and entertaining. His observations are insightful, intelligent, and most important, hilarious. And I never fail to be amused at his oft-used words "monster"and "gross."*

Before the show, I spent some time with another object of my affection - historic architecture. I am frequently in the city, and more often than not, my feet point me to the paths, streets, and cobblestones of Beacon Hill. Unlike some west-coasters, who grumble at New England's weird, little roads and non-sensical city layouts and street signage, after a decade here, I'm still charmed by it all. The appeal of the efficient wide, open roads and tidy, easily-accessed strip malls of the west has evidently gone over my head. (And really, doesn't the ill-logic of preferring the difficult drives and tight, centuries old construction simply because that's the way it's always been done, make me an honorary New Englander?)

(On my favorite street) Shirt: Anthropologie | Jeans: AG Jeans | Shoes: Jack Rogers

But honestly, who cares about efficiency when you're walking through the streets of Beacon Hill. Even if I twist an ankle on those cobblestones (hasn't happened yet) or stub a toe on an upheaved brick (happened more times than I can count), I will never stop visiting it nearly every time I'm in the city.

Hidden gardens are a big thing in Beacon Hill. So big, in fact, there is tour of them every May.

Not far from Beacon Hill, a walk through the common was all that was required to get to The Wilbur Theater. Luckily, I was there in plenty of time to purchase a couple posters, a Canadian House of Pizza and Garbage t-shirt**, and sit down with a glass of wine in the theater before the show started.

If the man on the side of The Wilbur looks familiar, you may know him as the Deranged Millionaire and resident expert on The Daily Show or as a PC personified in the old Apple Mac commercials (you may even recognize his voice as the dad in Coraline), and I've enjoyed all of it, but what I love the most is John Hodgman just being himself on his podcast. And that's who he was in his show, Vacationland. Just himself. His wry, witty, intelligent, morbid self. And I say morbid with great affection, as I am one who is also touched with a bit of the melancholy.

Taking its name from Maine's state motto, Vacationland is a journey through Hodgman's life. It begins with his childhood outside of Boston where, due to his status as an only child, he became part of the "super smart, afraid of conflict, narcissists club." (It's a club to which I feel I also belong. Though growing up in a Mormon family of six kids, I'm not sure how I got my membership card. Clearly, I am a monster.***) He takes us through each stage of his life with his own brand of honest, perceptive, humorous storytelling. The anchor story throughout centers on his recent summers spent in Maine, where he and his wife purchased a vacation home. Maine, with its harsh climate and jagged rocks, becomes a metaphor for mortality, as his time there coincides with reaching middle-age and facing thoughts of death. I know that sounds depressing, but it wasn't. Each observation was witty, his honesty and self-deprecation was endearing, and he had the audience laughing all night.

It is Hodgman's unique way of acknowledging the often disconcerting realities and ambiguities of life in a light-hearted, humorous way that helped me through a difficult time recently. Dealing with some past childhood issues and leaving behind my lifelong belief system, I was sent into an existential tailspin. I mourned the certainty with which I used to view life. On the days I wanted to escape my own dark thoughts, I would listen to the Judge John Hodgman podcast. Even though the cases brought to the podcast are trivial, his funny and perceptive remarks about the universal human condition, even in small things, helped pull me out of my funk and laugh about it. He helped me realize that we're all just going through the same thing, no one really knows what's going on, and really, it's kind of funny.

When I met John Hodgman after the show, I wanted to tell him that bringing levity to the ambiguities I had wrestled with brought me invaluable moments of reprieve during that struggle. But did I? Well, you remember Tracey Ullmen and Conan, right?

So, I'll say it now. Thank you, John Hodgman, and to repay you I made you take a picture.****

*Inside podcast references. I apologize for leaving out those who are unaquainted. Gross. I'm a monster.
**Another podcast reference. Episode 38 - Pepperoni Pauper. Listen to it, guys. Trust me.
***Did you catch that Hodgman oft-used word reference? Good for you! Now you're getting it.
****A reference to Hodgman's thoughts on picture taking. Just go listen to the podcast already!


  1. Great post Alyson! You aren't alone in your obsession with Beacon Hill :-) I love that golden retriever by the way - I have him in one of my snaps too!

    1. Thank you, Deb! Isn't that golden retriever the best?!

  2. Hello,

    Wow, beautiful pics ! :D

    Sarah, http://sarahmodeee.blogspot.fr/

  3. Excellent post! For sure I'll listen to his podcast.
    I feel the same way about celebrities. I might gasp, get wide eyed, and let a giggle escape, but approach them is a no. I prefer to respect their free time.
    I grew within a huff and puff walking distance of Boston. I only remember being around Beacon Hill once. You've been there more times than this native to the area. Therefore, I'm good with your being an honorary New Englander. Your body may have been born elsewhere, but your soul is born in New England. :)

    1. Thanks so much!! And I'm thrilled to be named an honorary New Englander! ;)

  4. I enjoy your Instagram so much, that I keep forgetting to go to your blog! I am fortunate enough to work in the city and spend many happy hours tromping around Beacon Hill.

    I saw Al Franken once, while waiting to be seated at SNL, and managed a totally lame, "hey, you're Al Franken!" and he said, "Yes, yes I am". Cured me of hailing celebs.

    I will be adding John Hodgman to my podcast list.