Getting off at the Amtrak at South Station, I immediately felt the shift that Boston has its own distinct vibe compared to my home city of New York. It’s not as loud or sprawling as the Big Apple, but it hums with its own character. One that’s charming, has narrow and cleaner streets filled with dogs owners, where shiny towers of a moderate height, sit beside historic landmarks, and the Freedom Trail winds through clusters of tourists and locals alike.
I was in town for a short weekend, and like any other trip, to make it memorable having good eats is a priority. But Boston proper has many options to chose from, which makes finding good eats for the short weekend a bit overwhelming. Luckily, with a little help from the Meet Boston team, I found four restaurants that delivered exactly what I hoped—great food, minimal wait times, and an experience that felt worth the four hour ride.
MIDA
My first stop; MIDA, the brainchild of Chef Douglass Williams, who reimagines Italian American comfort food. Greeted by a sign on the door that read, “Enter—you look great,” the vibe was immediately welcoming. Inside, natural light poured through oversized windows, bouncing off warm wood tables and a striking bottle-lined bar. It felt like the kind of place to celebrate a milestone birthday—lively yet intimate.My friend and I started with the Glazed Duck Wings ($14), sticky-sweet with a Luxardo cherry agrodolce glaze. Not traditionally Italian, but somehow it worked. At our server Erin’s suggestion, we added the Roasted Carrots ($12) from the Sides: tender, bright, plated with sumac yogurt and a cherry-almond drizzle—unexpected but good. 
Though the Eggplant Parmesan ($24) and Roasted Chicken ($29) were tempting, pasta was the obvious choice. I had the Gnocchi Cacio e Pepe ($19)—pillowy gnocchi tossed in Parmesan, olive oil, and cracked black pepper. My friend ordered the Spaccatelli al Pesto ($20), its smoky tomato undercurrent prompting a satisfied “oh this is good” after every bite. A Syrah Grenache paired beautifully with my dish; the Riviera del Garda Classico was perfect with the pesto. We finished with pistachio gelato ($8) and almond cake ($9), the latter topped with a glossy fruit compote that balanced tart and sweet.
75 Chestnut
The next morning, after a stroll through Boston Common, we wandered into Beacon Hill to check out 75 Chestnut. Tucked along a cobblestone street, this cozy spot feels like a slice of old Boston: all warm wood tones, charming art, and rainy-day comfort. Sitting by the window, I overheard regulars debating whether to order the Fried Chicken and Waffles ($24.95)—and once we saw they ordered the golden cakes, and it appeared on the table we followed suit.
Once we got our order, we knew immediately there were no regrets. The chicken was crisp, the waffles airy, and with a drizzle of syrup and hot honey. It’s the perfect brunch dish. We also ordered the restaurant’s namesake omelette: spinach, mushrooms, cheddar, served with brunch potatoes and sausage. A solid dish, but if you have to choose one, go for the chicken and waffles. Coffee is bottomless. Mimosas and Bloody Marys are available, but for a non-alcoholic option, the Spring Break mocktail hits the mark: Seedlip Agave, lime, pomegranate, pineapple, and a splash of sparkling water. Beyond brunch, 75 Chestnut offers breakfast, lunch, and dinner, plus themed nights like Wine Wednesday and Supper Sunday.
Bar Volpe
At Bar Volpe in South Boston, James Beard Award winner Karen Akunowicz brings her love of Southern Italian cooking to life in a large space that she played a hand in transforming. Walk inside and you’ll see floor-to-ceiling windows flooding the restaurant with light, while leather accents, marble floors, and two bars—one for cocktails, one for housemade pasta.
For dinner, we started with the Chopped Salad ($15): sharp caciocavallo, soppressata ribbons, oregano, and puffed white beans that make us forget croutons ever existed. Then tried the Grilled Octopus ($22), smoky and tender, plated over a warm Sicilian chickpea stew—it’s great to share dish or enjoy on its own depending on hunger levels. Another sharable item, the Farro Arancini ($8), a twist on Italy’s iconic street food. Karen swaps rice for farro, adds truffle, orange blossom honey, and fries them golden. For the mains—you’re here for the pasta. Chef Akunowicz is known as the Queen of Pasta in Boston. For any Kelly Clarkson Show fans, during the pandemic you may have seen her on your screens. Chef helped you and millions who were watching ,recreate authentic Italian cuisine in the comfort of your home.
At Bar Volpe we tried her Orecchiette with Lamb Ragu ($25), a dish native to Basilicata. Leftovers of it would be a dream, but odds are you’ll clean your plate, like we did. Other pasta options that caught our attention but unfortunately we did not have the stomach space for were the Ricotta Gnocchi ($32) with caviar, chives and lemon butter. And the Casarecce Al Nero ($40) with lobster, chili crisp and squid ink. However we made some room for dessert, once we saw Pistachio Gelato ($8), we looked no further and was pleased to see it wasn’t bright green.
Rose Town Kitchen & Bar
Rose Town Kitchen & Bar, located above the Canopy by Hilton Boston Downtown, isn’t trying to redefine Boston dining. But it does offer a solid meal and views. It was my final stop before catching the Amtrak back to New York, and brunch was in order. I ordered the Greek Yogurt Parfait ($15), layered with honey, fresh berries, and house-made granola. It is on the lighter side but it hit the spot. A heartier option would be a Build-Your-Own Omelet ($26), where you can fill it with, spinach, and cheese. And on the side; fresh cherry tomatoes, and an English roll. The scene around me said it all: a European couple sharing a sandwich before their walking tour, a family splitting Nutella crepes, and a birthday group posing by the neon sign. No, it’s not the place to try the best classic New England clam chowder or lobster roll, but for a convenient, crowd-pleasing meal close to major sights, it’s worth the short climb up one flight of stairs.
