Upstairs on the Square

Upstairs on the Square - 91 Winthrop Street, Cambridge (Harvard)

This fall (this post is really old), thanks to Gilt City and my friend Laura, I had an opportunity to try out the 5 course tasting menu with wine at Upstairs on the Square, a pretty swanky place in Harvard Square, with Ann and Laura's friend Dan.  I didn't really know what to expect coming in, other than the excessive amounts of pink and stripes used in the dining room decor were not to my liking.

Upon arrival, my concerns about the decor were found to be mostly true, though not as bad as feared.  However, things became immediately better when we were presented with the menu.

Let's just say it was a very enjoyable meal.  The wine pairings were all good, though I'd say the wine that stood out the most for me was the Sauvignon Blanc.  It was probably the best one I've ever had, though that could have had something to do with the fact that our server told us it was a limited edition run that this guy makes only in certain years.

The Heirloom Salad was good, especially the goat cheese, although sometimes the tomatoes were a bit overpowering for me.  Same for the Spaghetti au Caviar, although it was good just to have a small portion because it was kind of creamy and that would have become too much if we had tried to eat a whole entree of it.  The Salmon was probably the consensus top entree pick out of the group.  Here is a dish we wish they didn't have a small portion for.  The Salmon itself was great and then the root vegetables and apples were a perfect compliment with a kick from the mustard and horseradish.  It was especially nice for fall.  The Chicken was also great, although I would say the portion was even more noticeably undersized.  I was mostly surprised at how much I enjoyed the spaetzle.  At this point in the evening, we were all feeling pretty good from the wine and had been truly enjoying the assortment of fine foods presented to us.  I do not think we were prepared for what happened next.  The Churros y Chocolat is probably the best dessert I have ever had.  Ever.  They were perfectly fried and sugary and cinnamon-y and you could dip them in molten dark chocolate.  Pairing it with cinnamon ice cream just completed the perfection!  Needless to say, we all left on a happy note.


Doing the tasting menu at Upstairs on the Square was certainly an enjoyable experience.  The food was very well conceived and prepared, leading to the results described above.  It was different enough to be exciting, but familiar enough to be enjoyed.  Our server was very friendly and we had a good time, though there were a couple of overly long delays between courses.  My biggest knocks on the place are the prices and the atmosphere.  It's certainly worth the extra cost for a special occasion based on the food, but the dining room was a little off and also had too much of a stuffy, formal feel for me to make it a top choice.