If swapping out your t-shirts for sweaters and flip flops for boots has got you feeling bummed out, there’s one seasonal switch you can look forward to. Your favorite eateries around town are trading light and zesty flavors for warm, savory treats that will keep you feeling cozy all season long despite the chill in the air.  

Georgetown Cupcake

83 Newbury St.

Back Bay


Some might say Georgetown is a bit of a hub for tourists, especially on weekends, but the hotspot draws traffic because its moist fluffy cakes are tough to beat. After wandering along Newbury street on a crisp fall day, there’s no better way to unwind than by setting down those shopping bags and picking up one of their seasonal treats. Throughout October they’re offering a pumpkin spice cupcake topped with maple-cream cheese frosting and a shimmering fondant maple leaf, and a pumpkin cheesecake cupcake, which is a cheesecake cupcake infused with pumpkin and covered in maple-cream cheese frosting.

Cookie Monstah

Check site for truck location


This cookie sandwich truck is adding some spice to its thick, soft cookies and rich ice creams. For cookies, they’ve got ginger molasses, snickerdoodle, pumpkin chocolate chip and “cinnabon,” an oatmeal, cinnamon chip and white chocolate chunk cookie. Plus, you can choose from new ice cream flavors, such as pumpkin or apple crisp. For the full Cookie Monstah experience, inundate your taste buds with autumnal flavor by trying their Cinnabomb cookie sandwich (apple crisp ice cream tucked between two “cinnabon” cookies) or the Pumpkin Patch (pumpkin ice cream sandwiched between two snickerdoodle cookies).

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Union Square Donuts

20 Bow St.


& Boston Public Market


The much-hyped artisanal donut shop is known for its creative flavors, and you can expect nothing less from its fall menu. Union Square has chosen to go with apple as their big fall flavor rather than its fierce fall competitor, pumpkin, and is offering an apple cider cake donut, an apple crisp donut dipped in an apple cider glaze and topped with oats and a vegan apple spice donut infused with clove, nutmeg and cinnamon. For a change of pace, also try the “FluffaNutta,” a donut filled with homemade peanut butter cream, topped with a hefty blob of marshmallow Fluff and sprinkled with crushed peanuts.


481 Cambridge St.


& 617 Centre St.

Jamaica Plain


Fomu is known for its homemade small-batch vegan ice cream, but whether you’re dairy adverse or an ice cream traditionalist, you’ll leave satisfied. Since Fomu sources many of its ingredients locally, seasonal flavors are in no short supply here. They have pumpkin caramel ice cream, apple cider donut ice cream and mulled cider sorbet. For those who would rather save the ice cream for warmer months, Fomu has all its bases covered with a pumpkin white chocolate layer cake, pumpkin dulce cupcakes, caramel apple cake, and pumpkin spice whoopie pies. The drink menu has been revamped too—we’re talking pumpkin chai lattes, pumpkin pie frappes, apple pie frappes, and spiced hot cider.


134 Hampshire St.



If you’re looking to take your relationship with fall fare to the next level, incorporate some autumnal flavor into your main course too at Oleana, a Middle Eastern restaurant that sources produce from its farm in Sudbury. This season, they’re pairing seafood dishes with warming seasonal vegetables. Try the Acadian redfish with honeynut squash dolma, jeweled rice and orange blossom or the scallops with pumpkin guvec, leeks, tomato and pomegranate. Then if you’ve got room for dessert, go all out with the candied pumpkin with chestnut creme and milk chocolate sorbet, topped walnuts.