Super Square Boston: 5 Brilliantly Uncool Hangouts

Discover Boston nirvana in the opposite of hip

In modern-day Boston, you can eat a meal that consists only of vapor and be served by a state-of-the-art robo-chef; you can drink unique craft beers made by men with unique craft beards, or chance upon a guerilla pop-up food cart in a back-alley basement; and you can buy a limited edition pair of sneakers in a cult apparel store disguised as a mini-market.

However, not everything fascinating in town is rooted in data science, ironic tattoos or the approval of teenage influencers. Here are five ways to spend a day in Boston that will give your grumpy, defiantly untrendy Gen-X uncle the impression that culture has not been completely hijacked by hipsters, tech-nerds and what he insists on calling the “insta-twit conspiracy.”

Boston Public Library

We all know that we’re supposed to slow mankind’s inevitable descent towards idiocracy by championing—and maybe even reading—books made from paper. But modern reality is a life measured out in thumb-scrolls, to the rhythm of driving directions announced by the robot lady in our cell phones. Pretend it all ain’t so by hanging out in the splendid Boston Public Library where attention spans are measured in hours, not seconds, space is divided by the light from gorgeous green reading lamps, and delightfully grouchy oldies debate civic politics on live public radio broadcasts. Paradise.

Joe Perry's axe at Hard Rock Cafe Boston

Hard Rock Cafe Boston

Nothing says “I’ve seen the world” like a medium-well burger and soda from the Hard Rock Cafe. Here your eyes and ears are opened up to the olden rock universe in its entirety, as if the glory days of MTV never ended and the last word in sonic excellence was power-screeched by local rock hero Steven Tyler. On display is a pinstriped jump-suit in which Tyler used to strut, a guitar Joe Perry used to fret, not to mention Madonna’s Blonde Ambition Tour bustier and other artifacts from an era that’s no less alien than a mullet on 21st-century Newbury Street. Naturally, the sound system really rocks.

Superior reading materials at North Station

North Station Bar

On TD Garden game days and concert nights you can’t get a seat here, and during the regular commuter grind it’s a real-life version of Billy Joel’s classic boozer’s lament, “Piano Man,” minus the ivory-tinkling jollity. All of which makes it, in our estimation, one of the city’s greatest hangouts, and a fine place to make love to your tonic and gin. Eavesdrop on a never-ending series of Bostonian brief encounters, pick up a copy of Where Boston at the information window, plug directly into the nervous system of the Celtics/Bruins fanbase, and order another shot safe in the knowledge that you can’t miss the last train home (because your boutique hotel is only five minutes’ walk away).



Too much of the world, Boston is no bigger than a barroom that was once broadcast on primetime TV for twenty minutes at a time, and at Cheers just off the Public Garden, you can go one better than merely watching re-runs. Though a local has never set foot inside, hop in line and join the throngs of tourists eager to block out anything else this city has to offer. Originally called the Bull & Finch, this Beacon Hill location was the actual bar on which the series was based—the name-change happened in a genuine life-art-life mutual imitation kind of way. Barman, a warm glass of nostalgia, please.

Swan Boats

Swan Boats

While half the city zooms into the future on ride-share electric scooters, there’s a niche in Boston transportation that practically predates the horseless carriage and belongs exclusively to the foot-powered catamaran. The creation story of the Public Garden Swan Boat requires passing knowledge of Wagner’s “Lohengrin” in which a knight crosses a river on a swan-drawn pontoon—try impressing that on a generation less attuned to 19th-century romantic opera than to “Gangnam Style” and “Poker Face.” These floating park benches, which move at a pace that can only be described as geriatric, may not seem cutting-edge, but they’re eco-friendly and, in their own gentle way, rather epic.

Mike Hodgkinson
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