Dear Annie specializes in wine and small plates. (Photo: Brian Samuels via Dear Annie on Instagram)

What do you do if you run a successful locally sourced restaurant or a specialty wine bar in Somerville and are champing for a second act? The tasty, happy answer is to unite and invade Cambridge. That’s the story behind the wine bar and eatery Dear Annie, which set up shop just a few weeks ago on Massachusetts Avenue between Harvard and Porter squares in the digs that used to house the Nomad specialty clothes, decor and home goods store – now just 50 yards up the street. In short, the folks behind Rebel Rebel Wine Bar in Bow Market and Field & Vine, around the corner in Union Square, have created in Dear Annie a uniquely homey community space to nosh, talk and interact while sipping some very fine wine. It’s a cozy space, bohemian in ambiance, that’s essentially one large room with a community table at center and, sprinkled around the perimeter, some smaller drink tables with built-in bench seating with throw pillows and poufs. Given the uptick in Covid cases, that arrangement might give you pause, but Dear Annie is on it: No proof of vax, no sit-down. There is a decent street-side dining patio well equipped with heaters if that makes you more comfortable, but really the indoor closeness is no more an issue than at any other bustling restaurant or sports pub when the red-hot Pats are playing.

Onto the important stuff: the food and the wine. You get a seat and a menu; go up to the bar counter that fronts the open kitchen and place a food order; for your wine, you don’t make your own choice – you just tell the folks behind the counter your color and your yen and let them work their magic for you, peppering you with questions and offering tastes to get it right. Most of the wines sold (and you can pop in to get wine to go) are from organic, women-run wineries, and reasonably priced, given the niche. One thing I love about Rebel Rebel and Dear Annie is their fairly robust orange wine selection, an option that lacks at most Boston area restaurants and liquor stores. Everything orange I have had at both places has been beyond pleasing. 

The bohemian vibe at Dear Annie centers around a communal table. (Photo: Tom Meek)

Dear Annie is a tapas bar by default, with an accent on fish. Nothing on the menu is over $20. What pops are the deviled eggs with caviar, Arctic char tartare (one of my favorite esoteric fish, along with butterfish), Jonah crab toast and the “not tinned” house-cured fish selections (just do it; they’re seaworthy palate pleasers) that include salmon, bluefish and cod with crostini, pickled veggies and accented dipping arrangements (chili oil, mustards, herbs, etc). There are salads and cheese plates, as well as sandwiches such as a smoked mozzarella with anchovy that grabbed my eye. On a recent visit I had the mushroom panini, a hot pressed sandwich filled with an assortment of what tastes like just-picked fungi cooked al dente so you can taste their fresh, feral nature. They’re peppered with a mix of fresh seasonings, garlic and herbs and cheese that was so lightly used – and rightly so – that I could not detect if it was smoked mozzarella or Gruyere. Near the ends, the bread suffocated the grandeur of those marvelous mushrooms. If I had one druther, it would be to fill it up more, or maybe use less dough.

I honestly can’t wait to go back. There’s nothing listed that doesn’t appeal to my flexitarian desires, and I have the urge to run the menu top to bottom. Did I mention desert? It’s just apple, sweet potato or miso pie slices – catches the eye and makes your mouth water a bit, right? Dear Annie is open only Thursdays through Sundays and fills up fast. Can’t get a table? Get a taste-selected bottle of wine and show up earlier next time.

Dear Annie (1741 Massachusetts Ave., Baldwin near Porter Square)


Cambridge writer Tom Meek’s reviews, essays, short stories and articles have appeared in WBUR’s The ARTery, The Boston Phoenix, The Boston Globe, The Rumpus, The Charleston City Paper and SLAB literary journal. Tom is a member of the Boston Society of Film Critics and rides his bike everywhere.

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