Tomato Dinner at Upstairs on the Square

A couple of years ago, five Boston bloggers who had just started to get to know one another got together for a tomato dinner at Upstairs on the Square in Cambridge. Alicia, Daisy, Megan, Michelle, and I became fast friends over dinner, and tow years later, have had tons of food-related fun together, from a trip to King Arthur Flour, a big potluck, and a bachelorette weekend. Over the last two years, we’ve been through moves, job changes, and lots of wedding planning, and I am definitely glad we all met!

Last week four of us (missing Alicia!) got together for another tomato dinner at Upstairs on the Square, to enjoy some local tomatoes, wine pairings, and most of all, a chance to catch up on our busy lives.

I arrived first and read through the Upstairs on the Square wine and cocktail menus. Both are great, offering lots of variety, including five Champagne cocktails on the cocktail list. Be still, my bubbly loving heart!

Upstairs on the Square is hosting Summer of Riesling with a hilarious kick; they have paired a Riesling with a character from the Golden Girls! I laughed out loud reading about this diverse flight. I love pairing wines with things that aren’t just food, like music, and I thought this was brilliant.

Summer of Riesling

Once we were all at the restaurant, we headed upstairs for dinner. I love, love, love the décor at Upstairs on the Square. Purple and pink and big windows, comfy cushions, and lovely wall sconces all make for a memorable, quirky dining space.

Upstairs on the Square

We all went for dinner with the wine pairings. I love how wine can be paired to enhance food, and I also love a surprise in my glass.

Upstairs on the Square

Our first course, a green tomato gazpacho, was paired with an old favorite, Bonny Doon Ca’del Solo Albarino. We’ve visited Bonny Doon and even tried to become wine club members before remembering how difficult Massachusetts makes some wine deliveries!

The acidity in the wine paired nicely with the cool tomato soup.

green zebra tomato gazpacho


Bonny Doon Albarino

Our second course was definitely my favorite; you can not go wrong with tomato, peach, and lobster salad! Everything about this salad said summer, including the Sybille Kuntz Riesling, with its balance of sweetness and acidity.

brandywine tomato, peach, and lobster salad

Our main course, fire-roasted Berkshire pork, was delicious, but a little too much for me. It came with fresh fennel pollen, and I loved that fennel flavor that coated the meat. The wine pairing, an Occhipinti Frappato from my obsession, Sicily, was perfection. There were some nice strawberry flavors, but the wine had some herbaceous notes as well, which went nicely with the fennel.

fire-roasted Berkshire pork

Finally, we had dessert, tomato sorbet with candied pine nuts. I loved the pine nuts but found the tomato flavor in the sorbet a little overwhelming. A nice sweet South African wine, de Trafford Straw Wine, balanced out some of that tomato-y flavor. Just a sip goes a long way with a wine like this!

tomato sorbet

We had a blast at dinner, and the food and service at Upstairs on the Square, pleased, as always. It’s a gorgeous restaurant, and I am looking forward to a return visit to try out their Champagne bar.

I also look forward to eating tons of tomatoes over the next few weeks. Summer is flying by!

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Tags: cambridge, Dining out, dinner, Food, food and wine pairings, restaurant, tomatoes, Upstairs on the Square

  1. Alicia’s avatar

    Looks terrific!! Wish I could have been there!! Miss you girls like crazy!


  2. Bianca @ Confessions of a Chocoholic’s avatar

    I love the decor at Upstairs on the Square, and it’s so perfect for girls’ night out!


  3. Lindsey @ BeantownEats’s avatar

    I love when restaurants (and chefs) can have a sense of humor, like having a Golden Girls flight, and not take themselves too seriously! Your dinner looks delicious!


  4. Daisy’s avatar

    I am so glad we got to do this dinner again, two years later. I think it will be a tradition for many years to come.


  5. Megan’s avatar

    Just have to say my post is already written and the beginning sounds an awful lot like yours… you’ll have to wait til Wed to read. We must have been on the same wavelength though!

    I love this tradition, and I’m so glad we were able to get together for it this year. Maybe we’ll get Alicia to join in again next year!


  6. Michelle Collins’s avatar

    I have never been to Upstairs on the Square, despite living 7 minutes from it. I really need to check this place out!


  7. Elizabeth’s avatar

    This dinner sounds fantastic! Love the tomato and peach combo


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