A Beantown Birthday Bash: My 29th in Boston
Turning 29 is...a lot. It’s the age where you start checking your hairline a little more nervously and Googling “is 29 still young?” (It is, by the way—don’t come for me.) Naturally, I decided the best way to embrace this milestone was to distract myself with pizza, beer, and a city that oozes historic charm—Boston.
My fiancée and I flew in for a quick weekend getaway. Our base of operations? The Moxy Hotel near Tufts Medical Center. If you haven’t stayed at a Moxy, imagine what would happen if Instagram designed a hotel. Neon lights, funky decor, and a welcome cocktail at check-in? Yes, please. It was steps away from the action—or just a short Orange Line ride to downtown, which felt like cheating since Boston is such a walkable city.
The first stop on every Boston trip of mine is Regina’s Pizza in the North End. This place is an institution—like the Harvard of pizza. Between the perfectly crispy crust, the bubbling cheese, and the decades-old brick oven, it’s the kind of pizza that makes you rethink all your life choices that didn’t involve eating it sooner. We wandered the North End afterward, debating whether it’s humanly possible to fit a slice of Mike’s Pastry cannoli in after pizza. (Spoiler: it is.)
Bates Hall
The next day was all about playing tourist. Boston’s winding streets and gorgeous old architecture make even the most casual stroll feel like you’ve been transported back to colonial times, minus the powdered wigs. Our main stop was the Boston Public Library—a place so beautiful it makes you want to read books you know you’ll never finish. My fiancée spent time in Bates Hall, a majestic, cathedral-like reading room, studying away like a modern-day Hermione. Meanwhile, I wandered around pretending I was cultured and snapping way too many photos.
The evening was dedicated to Boston’s unofficial specialty—Irish pubs. The Green Dragon, The Black Rose, and JJ Donovan’s were our top picks. It turns out our “one drink” plan at each bar wasn’t entirely realistic. Each pub had its own vibe, great beer, and locals who were more than happy to share a laugh.
Day three was the main event: a Red Sox game at Fenway Park. Not just any seats, though—we were perched atop the iconic Green Monstah (cue your best Boston accent). Seeing the game from up there was surreal. Feeling the buzz of the crowd. When the game-winning home run landed just three rows in front of us, it was like the city was throwing me a personal birthday party. I knew I could never top this birthday. Well, maybe if I’d caught the ball...but hey, you can’t have everything.
We wrapped up our whirlwind weekend with a stroll along Boston Harbor, where we stumbled upon a bagpiper playing under Rowes Wharf’s grand archway. The sound carried across the water in a way that was both haunting and magical. It was one of those unexpected moments that makes traveling so special—and yes, it made turning 29 feel just a little less scary.
Boston, as always, delivered. Great food, great people, and an absolutely unforgettable birthday. Now if you’ll excuse me, I have to Google “things to look forward to in your 30s.”
