Entering Massachusetts, an ode to a complicated state

Saturday morning the car chugged up some state route in New York until, out of nowhere, a wide white sign with a state seal and bold, black typography reading “Welcome to Egremont.”

For those who don’t know, that wide white sign is a sign you see all over Massachusetts, which is where I was over the weekend as part of my Appalachian Trail Road Trip book (spring 2019, Hachette Book Group). The sign shows up at the border of whatever town you’re crossing into, a hefty, steel-footed welcome to whatever chunk of the Bay State you happen to be visiting at that time. They look old-fashioned and kitschy, yet oddly comforting, especially when standing on leaf-covered grass in front of a delicious mountain painting of reds, oranges and yellows. The signs immediately put you in Massachusetts. No other place in America has signs like these, signs that forcibly tell you all the time exactly where you are.

That, to me, is quintessential Massachusetts.

I first visited in September 1999, when my oldest brother took me to Boston to see a game at Fenway Park. This was during the ill-conceived “Turn Ahead the Clock” promotion, in which every team was supposed to wear “futuristic” uniforms during one home date of that season. My game? That was the Red Sox’ “Turn Ahead the Clock” game. Luckily the uniforms didn’t arrive at the park in time, or at least that’s the story the Sox gave the league. The Sox were allowed to wear their home whites. I sat behind a pole. It was incredible.

On that day I fell in love. I fell in love with Fenway Park, with the Red Sox, with Boston and with Massachusetts. My brother and I stayed with one of his co-workers out in Foxboro, and all I remember of the guy was he was part disheveled, maybe had curly hair, absolutely was Irish, and definitely spoke with one of the most incredible, jarring accents I’d ever heard in my life. The guy was cool.

I shrieked when I saw Fenway. My brother pointed out a Boston University building and predicted I’d go to college there. Not only did I go there, but I lived for two years and worked for four in that very building he pointed out. My brother literally correctly predicted where I’d live one day.

After graduating from Boston University I lived in eastern Connecticut, spending the first year out of college dashing back and forth to the South Shore, as I was dating someone living there at the time. So in those five years in and around Massachusetts I also fell hard for Marylou’s Coffee (their Twix iced coffee was my first iced coffee love), Shaw’s supermarket, pronouncing words incorrectly, the entire Sam Adams line of beer (Cherry Wheat especially), the CambridgeSide Galleria and candlepin bowling.

Massachusetts has a weird energy. Out east, especially, it’s full of tough people, guys and ladies with conviction, people looking shiftily one way or another. The Berkshires is funky – everyone is nice because I have to believe they’re trained to be nice (especially to the autumn leaf peepers who bus up to town to eat at their three-dollar-bill restaurants and sleep in their renovated Colonial inns) – but behind the tourism is an air of “can I just go hike for a little while?” So if there’s one word that aptly describes what Massachusetts seems to me (and this is coming from someone who had a Massachusetts address for four years) it’s “wary.” Everyone and everything is wary.

It’s not a bad thing, necessarily. It’s hard work living up to being the quintessential New England state, a place where the uber-rich can hunt for books and slurp ice cream by the sea, while the other uber-rich can walk outside a glamorous boutique hotel and point at a tree. It’s hard work living up to having one real city (come on, Springfield?) that tries hard to be cosmopolitan, but let’s be honest, the racial strife not too far under the surface is just too strong to deny (my own home city of Philadelphia has the same problem, of which I’ve been a part).

The point is Massachusetts is a tiny state that packs in a lot of things all the time. Pennsylvania is more than four times the size of Massachusetts and in no way packs in everything the Bay State can do. Massachusetts works overtime.

It was in full view during my trip up Route 7 this weekend. On a stretch of about 50 miles of road I experienced tourists glancing at colorful leaves and tour buses chugging through sleepy towns, the uber-rich in freshly pressed pants and crisp button-down shirts prancing to dinner at the newest James Beard-approved kitchen, the regular folk enjoying a beer and a ballgame, the hikers coming off the trail for a burger and some history, the truck drivers, the white-hairs in the convertibles, and the progressives with their stickers up in North Adams.

This is just one sliver of the state, a sliver defined mostly by the towering Taconic ridge to the west and the Berkshires to the east. The biggest mountain of all of these, Mount Greylock, stands in the middle of it like some omnipresent creature, keeping the clouds and shadows close by.

But that’s just this piece of Massachusetts. Go east and the land flattens, and the towns have their own little characters until you hit Boston, which is its own complicated thing. The shore towns are all a little different, with their own distinct people and customs and histories. The Cape and its islands? Same.

But there’s one thing that all of these towns have, no matter how weird or different or distinct: they all have those white signs. Entering (whatever you want to call us and however you want to define us). That’s Massachusetts.

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