Contessa [Boston]

Some families have milestone birthdays; others have milestone literature accomplishments. My younger sprout just finished To Kill a Mockingbird and in true younger-sibling fashion, insisted I bring her to Contessa, because that is where her sister and I ate after seeing the theatre production when she finished Mockingbird…

You may need to see here for context, and while I loved that thread, I decided Contessa deserves its own titled thread.

As seems to be standard there, we were solicitously seated by a charming waiter and ordered drinks- Shirley Temple, but made with seltzer rather than ginger ale to keep the total grams of sugar somewhat reasonable, and a cocktail for me. Something gin-based which looked too over the top, but the waiter assured me it was balanced and he was right- it was fantastic. As usual, big chunks of Parm with olives and a balsamic drizzle come to each table, and they additionally supply gluten free toast points for those of us who now with the march of time require them.

My sprout had the fusilli pasta with pesto for her main, and I decided to do a salad and app combo instead of a main, which turned out to be a fabulous choice as the artichoke salad may be my new favorite craveable dish. (It’s right up there with Branchline’s pea salad!) The tangle of mandoline-thin Jerusalem artichokes, tossed with roasted artichoke hearts, generously dressed and with mounds of Parm and almonds, hit every savory, tangy note I knew of and then some. My appetizer portion of calamari (gluten free owing to the use of rice flour) was also top notch. Truly, it was enough for a full entree, and I talked my sprout into helping me finish it and taking home half her pasta which I figured would reheat better. The calamari was crisp yet tender, and served with some indulgent butter-based sauce which those of us with mere mortal metabolisms should not be allowed to consume. If you’re used to “calamari” meaning fried-from-frozen rubber bands served with red sauce, this will blow your mind.

I know I’m being effusive, but we really did enjoy our meals that much. A gorgeous sunset with view out over the Common capped off the experience. We were too full for dessert (and at $16 with no gluten free options I felt we could do better elsewhere), so we hopped back on the green line and treated ourselves to some chocolate and caramels from Ball Square Fine Wines to eat on the walk home. Total dinner cost was about $120, (cuz the sprout is still free on the T) and no, it’s not earth shattering new cool cuisine, but it’s about the experience and the feel of luxury and a rare outing alone with one parent for a sprout. Throw in some actual delicious food, and we’ll be back.

Mission accomplished; onwards to some Steinbeck for the sprout. Do we eat at Cannery Row next??!



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Beautiful description and beautiful photos! I’m all in favor of celebrating literary accomplishments!

Ball Square Fine Wines has some great ice creams!

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We have a shortage of that. Bring it on!

I love your post and your Sprout.

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Wow, I have only experienced that in Italy.

Thank you for sharing your happiness with us here. We could all use more joy in our lives. Appreciated!

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Lovely, thanks for this. I just had lunch at Contessa with my daughter and we had a similarly lovely, if expensive experience. And I’m writing this from a meeting near Monterey, a stones throw from Cannery Row.

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Lovely report, thank you!

What a great write up! Makes us sound like sourpuss’ after our dining out experiences. :laughing:
So glad you all had a wonderful time.