I've been to Upstairs on the Square countless times. I've gone for Restaurant Week, Mother's Day and for a bridal shower, yet somehow my visits never made it on to the blog!
When one of my favorite girls asked if I'd like to help her spend her $100 gift certificate at Upstairs on the Square, I jumped at the chance! We made a reservation for tonight at 6:45pm.
I arrived a few minutes early and waited outside in the sunshine. Upstairs on the Square is located right in the heart of Harvard Square in Cambridge, next door to Peet's Coffee and above Grendel's Den.
In the summer time there is an outdoor patio, shaded with bright, yellow and blue umbrellas.
Everything in Upstairs on the Square is pink, purple, gold or animal print. That design starts on the sign over the door.
Then you walk up a leopard print set of stairs to the main dining floor.
There are two sections to the first floor - the front room which also houses the bar, and a second room which is basically a sun room and has beautiful views of the square.
Check out the zebra carpet in the sun room!
We were seated in the sun room at a cozy table for two. Our table was right next to the most fun piece of decor, a gold tree!
We hadn't had a sip or bite yet and I was already in love.
Our waitress came over and delivered four menus! The cocktail menu, the dinner menu and two special menus. One paper menu was the "Last of the Lot" bottles of wine, and the other was two drinks options, both to support fundraising for breast cancer research.
We ordered our drinks and I picked an option from the breast cancer research offerings. I chose the flight of roses, which was three glasses of rose wine - one Italian, one German and one from California. Not only were they delicious hues of pink, but they all tasted sweet and refreshing!
My dinner date ordered the dark and stormy cocktail. She said she thinks they make the best rendition. Apparently they make their own ginger beer! Look at the cool design they cut into the lime wedge!
While looking over the dinner menu, we were delivered a basket of bread with a bowl of dip that was olive oil, pesto and crushed red pepper. I really should put crushed red pepper on everything.
We were already having a tough time deciding what to get, when our waitress shared with us the specials for the evening. We immediately jumped on one of the appetizer specials - fried green tomatoes over smashed avocado, served with a lobster and blue fish salad. The fried tomatoes were fantastic and the panko breading was sublime!
Since we had cash to burn, we each ordered two plates for dinner.
My friend ordered two pasta dishes. First, the gorgonzola ravioli with braised short ribs and brussel sprout chips.
She also selected the gnocchi with ham, peas and spinach. The gnocchi (which I also tasted) was so light and creamy! This was absolutely the winning dish!
I ordered the asparagus with maple sugar custard. One side of the dish had three spears of asparagus topped with a light, butter based sauce and parmesan chips. The other side of the plate had a maple sugar custard which basically tasted like pure butter. In the best way. The custard was so good it felt like it should be illegal.
I also ordered the cauliflower strozzapreti which was superb. Vegetarian entrees can be lackluster, but this dish sang. Not only was the pasta itself delicious, the cauliflower was yummy and the lemon based sauce was a refreshing coating. I couldn't believe how scrumptious this dish was!
Though we were already bursting at the seams, we had to see the dessert menu. My friend selected the affogato - vanilla ice cream topped with chocolate sauce and served with espresso. You pour the espresso over the ice cream to create coffee ice cream. The plate was also garnished with two amaretto cookies, which tasted like macaroons. So good!
I chose one of the dessert specials, churros. The friend I was dining with is a friend from my time studying abroad in Spain where churros are common place. We were excited to taste this version.
I will say, the churros tasted more like fried dough than anything else. However, they were served with a cinnamon ice cream that tasted like Cinnamon Toast Crunch cereal! It was amazing! I could eat that ice cream every single day.
In addition to our stupendous meal, we also had the best waitress. She was friendly, high energy and extremely knowledgeable about literally every single dish on the menu. A server can make or break a dining out experience. I was so happy, I tipped her 25%.
Upstairs on the Square is a wonderful restaurant for a night out or a celebratory occasion. The location is tremendous, the design and decor are unique, the food is stellar and the service is excellent.
Visit Upstairs on the Square at 91 Winthrop Street in Harvard Square in Cambridge.
