Anneliese: Planning A Dinner Out in Boston

My birthday is coming up in two weeks, and with all of this end of the year chaos, I’ve been struggling to plan the perfect night out. I have my list of go-to restaurants, but I want to try something new for my birthday. However, for any of you who are also struggling to plan something special for a springtime birthday or just a final, end-of-the-year hoorah, maybe my list of favorite Boston spots will inspire a fabulous time for you and your friends.


33 Union St, Boston, MA 02108

This tiny, Belgian-themed joint by Faneuil Hall was probably my best Internet find EVER. The menu is scribbled on a chalkboard that wraps around the wall above the chefs’ heads, and features poutine (French fries drowned in gravy and topped with cheese curds), frikandels (not quite sure what they are, but they’re delicious), and, of course, Belgian waffles topped with homemade ice cream and your choice of saus. For those 21+, they have an extensive beer menu of high quality international (but mostly Belgian) brews that you have the option of turning into a beer float. The ambience of the place is great, with French comics covering the walls and indie rock sailing from the speakers. However, it’s quite small inside, so be prepared to lunge for the first open table you see.

The Friendly Toast

1 Hampshire St, Cambridge, MA 02139

(Kendall Square)

The perfect word to describe The Friendly Toast is kitsch (and I mean that in the most unpretentious way possible). The walls are lime green and covered in all kinds of bizarre junk you’d find at a flea market, the plates are mismatched, the seating is straight out of a 1950s diner, and there is a giant, smiling cheeseburger sculpture that watches you as you eat. The experience of eating at The Friendly Toast is enough to draw me back time after time, but the menu itself is beyond amazing. The flavors of their dishes are as mismatched as the décor (fries topped in bleu cheese and provolone, which you dip into a spicy, strawberry habanero sauce), and they serve breakfast all day. The restaurant presumably takes its name from its friendly (and quirky) staff and the multiple kinds of delicious breads that are baked there daily. Fun fact: It’s also conveniently located across the street from Kendall Square Cinema.

Five Napkin Burger

105 Huntington Ave, Boston, MA 02199

I try to avoid chain restaurants, but Five Napkin Burger is so great that I’ve made an exception. I will attempt to lure you in with two words: S’mores milkshake. There, are you convinced yet? If not, to state the obvious, Five Napkin Burger has some of the best (and probably most sophisticated) burgers in Boston. I actually had the fish tacos, not a burger, when I went there the first time, and they were amazing. Fish tacos are tricky and there are so many things that can go wrong in their preparation, so when I find a place that serves them right, it instantly win a spot in my heart. It also just feels really cool inside the restaurant, with subway tiles, dim lighting, and artsy light fixtures.

The Squealing Pig

134 Smith St, Roxbury Crossing, MA 02120

Even though it’s located down the street from the Museum of Fine Arts, The Squealing Pig is kind of hidden down a side street—but thank God I found it! The pub-style menu features a dozen or so sandwiches and toasties (I personally love the grilled salmon BLT) that are made with fresh bread from Iggy’s Bread of the World in Cambridge. They also have awesome pizzas (gorgonzola sirloin steak, fig and prosciutto, grilled asparagus, just to name a few) and a great seafood menu. There is one dessert on the entire menu, a Mars Bar toastie, which is a Mars Bar (essentially a British Milky Way), topped with bananas, grilled between two waffles, and served with homemade whipped cream and strawberries. If the menu isn’t enough to pull you in, they have live music five nights a week, including Folk Off Thursday, featuring Mike Barrett, “World’s most outrageous folk singer.”


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