The Eight Best Places to Find Delicious Cookies in Boston
Load up on classic chocolate chip, local spins like Green Monster Mint, one giant cookie sandwich, and many more creative confections.
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We’re not going to sugarcoat it: Sometimes you just need a cookie—or twelve. Others might serve a dessert guide like this with a side of guilt, encouraging you to enjoy treats in “moderation” or whatever. Not us: We’re here to tell you to go all in. So have a cookie for breakfast, a cookie for bed, and in between, a cookie with a side salad for a sensible lunch. Then start all over again.
Blackbird is famous, of course, for high-flying doughnut flavors like its luscious Boston cream, filled with silky vanilla bean custard. One of the surprise stars of the menu, though, is actually a cookie: the Cookie Dough-nut, naturally, which is (you guessed it!) a chocolate chip cookie in the shape of a doughnut. Some might call it an identity crisis, but we call it delicious—especially since its ring shape imparts extra crispy edges that are perfect for dunking in milk. Find the goodie at Blackbird’s locations in Beacon Hill, Fenway, the South End, Brighton, and Newton; the Harvard Square nesting spot is temporarily closed.
Multiple locations, blackbirddoughnuts.com.
In the North End’s sea of cannoli, Bova’s begs the question: What about Italian cookies? Answer: They’ll make you forget all about ricotta-filled shells at this 1926-founded, family-owned bakery, where the colossal collection of cookies includes stellar anise snowballs—drizzled with icing, topped with sprinkles, and with a licorice-y bite. There are other standouts: say, the chocolate almond meringue cookies, as well as those filled with zingy Amaretto orange cream. And don’t miss the traditional pizzelle waffle cookies, their doily-like appearance almost as beautiful as their delicate flavor.
134 Salem St., Boston, 617-523-5601, bovabakeryboston.net.
“Maca” is short for “macaron,” which is French for “merengue-based cookie sandwiches from heaven.” Praise be to baker Tamy Chung, who turned a pop-up operation into a brick-and-mortar business at Bow Market in 2018; there, she delights with playful flavor combinations like the cereal-invoking Fruity Pebbles, elegant lavender honey, slightly nutty pandan, and spirited Baileys Irish Cream, among others. Beautifully shaped and decorated to look like smiling rabbits, cute corgis, and other whimsical creatures, these cookie sandwiches are almost too pretty to eat—almost!—so be sure to snap a few pics before you gobble them up.
1 Bow Market Way, Somerville, 617-539-6227, macaboston.com.
Oakleaf Cakes Bake Shop
Yes, Oakleaf’s titular cakes are both gourmet (decadent yellow, chocolate and red velvet bases, all with vegan alternatives) and gorgeous, available for grab-and-go or ornate custom decoration. But the same could be said for the cookies: In fact, here, the humble sugar cookie is a delicious canvas for adorning with Oakleaf’s DIY cookie decorating kit, which includes all the royal icing and sprinkles you need to spruce up eight baked treats in seasonal shapes. Want the work done for you? You can still swing to pick up chocolate chunk and checkboard cookies, among other fresh-baked flavors.
12 Westland Ave., Boston, 617-299-1504, oakleafcakes.com.
Sweet Cheeks Q
We’ve already tipped you off to the sublime giant nutter butter cookie whipped up by Best of Boston-winning pastry chef Dee Steffen Chinn at Sweet Cheeks Q, but it’s well worth a second sugary shout-out. Although any visit to Tiffani Faison’s Fenway barbecue temple inevitably includes gorging on several pounds of sauce-slathered meat, leave a little room—because this peanut butter-filled cookie sandwich is gigantic enough to be a meal in itself. Oh, and while you’re in the neighborhood, be sure to check out Chinn’s other sweets at neighbor-sibling Fool’s Errand. During the pandemic, Faison’s intimate adult snack bar has transformed into a takeout window on weekends, with Chinn and Big Heart Hospitality’s wine director, Charlie Gaeta, most recently teaming up to provide creative cake and wine pairings.
1381 Boylston St., Boston, 617-266-1300, sweetcheeksq.com.
You can’t go wrong with any of the treats that stock the treasure trove-like glass cases at this snug Southie spot, from the sumptuous cheesecake to the lovely truffles (particularly boozy bites of orange liqueur-imbued chocolate). The cookies, though, are truly things of beauty: Each is a half-pound of scratch-made decadence with a slightly crunchy outside and a chewy inside. Signature oatmeal cookies feature dried cranberries with coconut and walnuts for a pleasant interplay of texture, while other standouts include peanut butter cookies studded with cashews and white chocolate. Plus, Sweet Tooth offers cookie dough pre-portioned in little balls to toss right in the oven, as well as cookie decorating kits that might actually make Zoom-based, work-from-home teambuilding exercises way more bearable.
371 W Broadway, Boston, 617-268-2555, sweettoothboston.com.
Sugar Baking Co.
Bring a big appetite, because this West Roxbury shop sells cookies by the pound. Take note from the regulars and stock up on the favorite brambles cookie, which is a raspberry-filled delight similar to a European tea cookie (though it pairs just as well with an extra-large Dunkin’ iced coffee as it does with an afternoon cup of Earl Grey). Don’t skip the stellar snickerdoodle either, or the gingersnaps that come with just the right bite of spice. The bakery offers free delivery within West Roxbury, though if you’re driving there from elsewhere in town, try not to polish off all the pecan shortbread (another must-try) before you get home.
1884 Centre St., Boston, 617-327-8427, sugarbakery.net.
Top Shelf Cookies
The first brick-and-mortar location of baker Heather Yunger’s Top Shelf Cookies is just about to ding done! in Dorchester’s Adam’s Village. Ahead of the spot’s imminent opening, though, you can already pick up her inspired cookie creations flavors at American Provisions markets in Dorchester and Southie—or just order online and have the morsels shipped to your door. The flavors are enough to make you homesick for the city you’re still living in, from the Fenway-inspired Green Monster Mint, a dark chocolate cookie spotted with green mint chips, to a molasses spice cookie named for the North End’s famous Flood. There are even beer-with-cookie combos, like Boston Lager Chocolate Chip and Winter LagerLand cookies, infused with Boston-born Sam Adams brews. If you’re too lazy to leave the house (who isn’t?) or want to send a gift to a Hub expat in your life, sign up for the Cookie of the Month Club, which sends a dozen delights to your door every month.