The Nine Best Places to Find Delicious Cookies in Boston
Load up on classic chocolate chip, local spins like Green Monster Mint, ice cream-filled cookie sandwiches, and more.
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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.
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.
Do you like cookies? (Yes, you nod.) Do you like ice cream? (Love it, you coo.) In that case, how do you feel about local-baked cookies sandwiching massive scoops of Massachusetts-made Richardsons ice cream? (SIGN ME UP, you scream.) Cookie Monstah, a Boston-area food truck turned multi-location bakeshop, is the operation to thank for these heavenly pairings, which run the gamut of combos: There’s the PB&J sandwich, for instance, which sidles strawberry ice cream between peanut butter cookies, and the Candy Shoppe sandwich of M&M cookies with Milky Way ice cream. Can you get the cookies on their own, as well? Absolutely. But why break up such a beautiful couple?
Multiple locations, thecookiemonstah.com.
This first Levain Bakery opened in Manhattan in 1995—the cult-favorite cookie maker has blown up in a big way, though, in just the last couple years. Besides selling into grocery stores, Levain has finally expanded its storefronts outside NYC, and that includes last month’s debut of a location in Boston’s Back Bay. Now it’s easier than ever to get our hands on its famous six-ounce cookies, offered in five different flavors: chocolate chip walnut, dark chocolate peanut butter chip, and oatmeal raisin, to name a few. And guess what? Expansion hasn’t diminished the quality of the cookies one bit: They’ve still got the perfect formula of crunchy outsides and warm, gooey centers.
180 Newbury St., Boston, levainbakery.com.
“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.
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
After years of selling her cookies to restaurants and retailers, in 2021 baker Heather Yunger finally opened a brick-and-mortar shop for her aptly named Top Shelf Cookies. It’s always a treat to swing by the Dorchester store and pick up standby-favorite flavors such as Green Monster Mint, a Fenway-inspired dark chocolate cookie spotted with green mint chips, or the Boston Lager Chocolate Chip infused with Boston-born Sam Adams brews. If you’re the type to appreciate a pleasant surprise, though, sign up for the Cookie of the Month Club, which sends a dozen unexpected delights to your door every month.