The Best Grilled Cheese Sandwiches in Boston

By Jacqueline Cain
MIKE AND PATTY'S - The Best Grilled Cheese Sandwiches in Boston
Mike & Patty's / Credit: Brian Samuels Photography

The grilled cheese is one of the easiest sandwiches to prepare, yet we still find ourselves ordering these versions around town. Because when we’re craving something crispy and absolutely oozing with hot cheese, we trust the culinary pros at these Boston restaurants and kitchens to take this classic sandwich to the next level. Next time you need a toasted taste of nostalgic comfort food, check out the best grilled cheese sandwiches in Boston.

Roxy's Grilled Cheese food truck
Brian Samuels Photography

This pick won’t surprise anyone—but it will satisfy all. More than a half-dozen grilled cheese options at Roxy’s Grilled Cheese run the gamut from a Classic Three Cheese—fontina, muenster, and Vermont cheddar—between slices of Iggy’s pain de mie (aka our favorite white bread ever), to the beloved Green Muenster, which ups the ante with bacon and house-made guacamole. Roxy’s, which has a food truck and brick-and-mortar locations in Allston and Central Square, also serves a trio of vegan grilled cheese sandwiches made with plant-based alts.

Exterior of Cutty's Boston
Credit: Brian Samuels Photography

Brookline lunch counter Cutty’s is more or less dedicated to sandwich perfection, and the Grilled Cheese is no exception. In this instance, you’ll be treated to your choice of well-buttered white or wheat bread stuffed with creamy, mild havarti and add-ons like ham, bacon, and fried shallots. Other options for grilled cheese enthusiasts include a pimento cheese version with a zesty house-made spread; and the Rabe T.J., which is a panini-style press of melty mozzarella, sharp provolone, tomato jam, and bitter, nutty broccoli rabe.

MIKE AND PATTY'S grilled cheese sandwich
Credit: Brian Samuels Photography

Grilled cheese sandwiches aren’t just for lunch (or dinner). The breakfast-friendly Grilled Crack from Mike & Patty’s piles fried eggs and two strips of bacon on buttered-up sourdough bread along with melty cheddar, Swiss, and Gruyère. Is it a grilled cheese? Is it a breakfast sandwich? Frankly, we don’t care what team it belongs to: It’s hot, cheesy, and delicious, and that’s what really counts. It’s available at Mike & Patty’s original Bay Village café, outposts at Bow Market and High Street Place, plus the growing company’s new Flourhouse Bakery in Newton.

Formaggio Kitchen - Boston's Best Cheese Shops
Formaggio / Credit: Brian Samuels Photography

Local gem Formaggio Kitchen curates a singular selection of cheese and meats at its three local locations. On weekdays, the cheese-loving team also puts together some delicious prepared lunch to go—including charcuterie sandwiches and a top-shelf grilled cheese on locally baked breads. Sandwiches are available at Formaggio Cambridge, Kendall, and South End Monday through Friday on a first-come, first-served basis, but you can always call in an order ahead of time at your preferred location.

Curds & Co. - The Best Grilled Cheese Sandwiches in Boston

This Brookline Village spot may describe itself as a “21st century cheese shop,” but Curds & Co. is not too fancy for grilled cheese. That being said, this is quite a special grilled cheese: Fresh slices of a locally baked Iggy’s French Pullman loaf are slathered in Cabot butter and filled with a blend of Jasper Hill Farm cheeses. You can further upgrade with onion jam, prosciutto, Serrano ham, pikliz, or other add-ons. Keep an eye on Instagram for a monthly sandwich special, too: Recent rotations have featured PB&J-inspired tahini and a fig-orange reduction; fresh goat cheese with a fiery combo of hot peppers, sriracha spices, and hot honey; and smoked gouda with harissa and a touch of fresh chèvre.

State Park

Interior of State Park
Credit: Brian Samuels Photography

Despite its delightfully divey vibes, this bar serves up some of the best food in Kendall Square. From pickle-brined Fried Chicken to whatever’s on the dessert menu, State Park deals in nostalgia and never takes itself too seriously, reimagining hangover-helping cuisine using high-quality ingredients. The Grilled Goat Cheese Sandwich is a fall- and winter-seasonal favorite, which fills toasted sourdough with tangy, fresh cheese, crunchy slices of apple, spicy hot maple, and crispy fried sage.

Dear Annie

Dear Annie Grilled Cheese Sandwich
Credit: Chris McIntosh

Dear Annie, an award-winning Porter Square wine bar from the founder of Rebel Rebel and the owners of Field & Vine, reimagines the community-centered idea of “pub culture” with natural wines and pescatarian fare. So, you won’t ever find slices of porky bacon on the grilled cheese offerings—instead, how about plump, sweet kernels of corn and strips of roasted poblano melting into sharp cheddar; or salty, fatty anchovies with a bracing, garlicky gremolata and smoked mozzarella? Chef Andrew Brady crafts oft-changing grilled cheese sandwiches on house-baked sourdough bread (the same thick slices that accompany the must-try Not Tinned Fish), using local cheeses.

Interior of Flour Bakery + Cafe
Credit: Brian Samuels Photography

One of our absolute favorite bakeries doubles as a top sandwich shop: Flour Bakery + Cafe is a lunchtime go-to in eight neighborhoods, from the South End to Central Square, thanks to stacks like a toasted-focaccia BLT, an Anchiote Chicken Sandwich with mashed avocado, and of course, a baller grilled cheese. The Grilled Mushroom Melt. Relatively new to the menu, this gooey delight features focaccia slathered in smoked gouda spread with roasted mushrooms, sherry caramelized onions, and fragrant fresh rosemary. It’s filling, sure, but you try walking out of Flour without a sweet treat for dessert. We’re picking the TCHO Chocolate Chip Cookie.

Eric Twardzik contributed reporting.

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