Dear Annie is a cozy gem with excellent vibes, a fantastic wine selection, and friendly staff, making it perfect for casual catch-ups or special celebrations.
"The menu at Dear Annie doubles as a zine with a grainy cover photo of Tina Turner and David Bowie sharing a swig from a bottle of wine. It’s a fitting image for a New American restaurant that encourages mingling both with people you know and those you don’t. At the massive 16-seat communal table in the center of the room, taper candles flicker on faces and someone is always just a glass of trousseau away from swiping the deck of Tarot cards on the table and reading your future. Inside that zine, bottles from small, low-intervention producers line up next to brief bios about the winemakers alongside a short menu of seasonal vegetarian and pescetarian dishes. You wouldn’t know it from the striped bass crudo coming out of the kitchen or the overall rich louche aesthetic—that table looks like “The Last Supper” styled by Bode—but this is a counter service spot. Order something to drink you’ve never heard of before and a couple of small plates, grab a seat at the table, and maybe make like Turner and Bowie and take some swigs straight from the bottle. Food Rundown photo credit: Jonathan Smith Smoked Mackerel Deviled Eggs The sliver of salty mackerel on these eggs is the perfect substitute for the sea salt often sprinkled on deviled eggs. Pop the whole thing in your mouth at once. It’s like eating an egg pulled from the bottom of the Harbor (complimentary). photo credit: Jonathan Smith Veg Out These roasted carrots come stacked like kindling in a teepee fire lay that would make an Eagle Scout proud. Doused in hot honey, salsa verde, and queso fresco, they’re soft but still have the echo of a crunch. Served with hazelnuts sprinkled on top, if it’s on the menu this dish is a must-order. photo credit: Jonathan Smith Sea Dog Advertised as a “Dear Annie classic,” the Sea Dog is essentially a fish cake smushed into the shape of a ballpark dog and stuffed inside a grilled split-top bun. Crumble up some of the house-made chips and throw them on top of the dog's calabrian chili aioli and cornichon relish for a taste of summer." - Jonathan Smith
"The (mostly) no-reservation policy at Dear Annie is part of the casual, communal charm that makes it one of the best wine bars in the Boston area. The team puts a few seats up on Resy each night, but the majority of the space is reserved for walk-ins. Besides great wine, expect a locally sourced pescatarian menu that adapts to the season." - Erika Adams, Karen Wilber
"Serving an extensive list of natural wines from small producers, Dear Annie is a collaboration between the people behind two Somerville establishments, Field and Vine and Rebel Rebel (another excellent wine bar in Bow Market). Serving an extensive list of natural wine from small producers and a smattering of small plates, this wine bar has attracted national media attention after it was named one of the new best restaurants in America by the New York Times and Bon Appetit." - Erika Adams, Valerie Li Stack, Rachel Leah Blumenthal
"The (mostly) no-reservation policy at Dear Annie is part of the casual, communal charm that makes it one of the best wine bars in the Boston area. The team puts a few seats up on Resy each night, but the majority of the space is reserved for walk-ins. Besides great wine, expect freshly baked bread, a menu that adapts to the season, and pizza night on Mondays." - Erika Adams, Karen Wilber
"One of Boston’s hottest restaurant openings of 2022, Dear Annie made appearances on multiple national best-of restaurant lists that year. It’s for good reason: From the spicy seafood fumet to the grilled cheese with pickled poblano peppers, the small-yet-mighty menu at this laid-back wine bar isn’t messing around. The crispy, Sicilian-style pizza on Monday nights is worth a special trip." - Julian Cohen, Eater Staff