Boston Birthday Weekend: A Whimsical Urban Adventure
In my ongoing quest to collect birthday memories instead of things, I whisked myself away to Boston for a weekend of baseball, country music, and wandering the unfamiliar streets of Boston.
*This adventure was from my 40th birthday
Salem: The Accidental Appetizer
Landing at 10am with hours to kill before a 4pm check-in, we made the executive decision to start our adventure in Salem. We did rent a vehicle and traffic was not pleasant. We weren’t craving the touristy witch hunt extravaganza—did that when I was 15—but for a taste of coastal charm before diving into Boston proper.
For lunch, we claimed a spot at Finz Seafood & Grill (76 Wharf St) with a prime view of the harbor. Let me tell you—watching boats bob on the water while demolishing a lobster roll and clam chowder is basically therapy without the co-pay.
Boston Back Bay
Our home base: the CitizenM in Back Bay (370 Congress St). It was super cute and had window overlooking the street.
Morning Runs: Communing with Commonwealth
Each morning, I laced up my running shoes and hit Commonwealth Ave like I was being chased by my own birthday cake. There’s something magical about running through a sleeping city with the sun rising and crisp air, dodging squirrels plotting world domination and nodding to fellow morning masochists. The tree-lined boulevard with its stately brownstones set the mood while I listened to my podcasts. I grabbed smoothies or loaded up bagels on the way back to the hotel, waking my boyfriend up with breakfast.
The Sacred Pilgrimage to Fenway
Fenway Park (4 Jersey St)—where even I, with my limited sports knowledge, could feel the weight of tradition in every hot dog eaten and beer spilled. The crowd’s synchronized cheering made me wonder if there’s a secret Boston handbook they distribute at birth with all the proper responses and when to yell “SWEET CAROLINE!” Everyone seated next to us became this temporary baseball family. In all the baseball games I have been to, this was had a special charm.
Literary Libations at Bukowski Tavern
Bukowski Tavern (50 Dalton St): Despite not drinking alcohol, I have an inexplicable attraction to dive bars. The Bukowski vibe was perfectly disheveled. I sipped my non-alcoholic hoppy refresher by Lagunitas while mentally composing terrible poetry in Bukowski’s honor.
Culinary Adventures of the Highest Order
At Piattini (226 Newbury St), we dove into Italian food in our date night attire. The food was fucking delicious.
The Boston cream pie from its birthplace, the Omni Parker House (60 School St). Listen, I don’t make the rules, but when visiting a city, you MUST eat its namesake foods. It’s like a cultural handshake, but with more calories and significantly more joy. This custard-filled, chocolate-topped wonder has been making people happy since 1856, which is longer than most governments.
Literary Landmarks: Boston Public Library
The Boston Public Library (700 Boylston St) is basically Hogwarts without the moving staircases. Its grand staircase and reading room have starred in more movies than some actual actors—including “The Departed” where it briefly class-upped all the mobster shenanigans, and “Pink Panther 2,” a movie that exists despite all evidence suggesting it shouldn’t. Walking through those hallowed halls, I felt compelled to whisper and look thoughtful, as if great literary thoughts might be contagious through proximity.
Suburban Excursion: Megan Moroney at Gillette Stadium
We ventured to Gillette Stadium (1 Patriot Pl, Foxborough). Since we had rented a vehicle, we were able to park at a local shop down the road for $20. I can’t imagine an Uber fee for that night. The car rental was cheaper than what Uber would have charged. We even spent one day with the car parked in the garage, taking the local subway into downtown. It was a blast and also cheaper than parking our rental all over downtown when we could scoot like locals.
I have such a girl crush on Megan Maroney. It was the final show of the tour.
Conclusion: Boston, You Quirky Gem
Boston exists in that perfect sweet spot between historical reverence and modern chaos—rather like my approach to birthdays. The city packs so much character into its winding streets that even getting lost feels intentional, like you’ve stumbled into a secret Boston side quest.
As birthday adventures go, this one hit all the right notes: good food, cultural immersion, physical activity, and enough memories to tide me over until the next journey.
Next stop: Wherever the birthday gods and discount airlines take me.
