Grilled Cheese Sandwiches

By Eric Twardzik

The grilled cheese might just be the easiest sandwich to prepare, yet we still find ourselves ordering it from the venues below. Because when we’re looking for hot cheese fix, we trust the culinary pros at these Boston destinations to take the classic sandwich to the next level.

Roxy's Grilled Cheese food truck

This pick won’t surprise anyone—but it will satisfy all. More than a half-dozen grilled cheese selections at Roxy’s Grilled Cheese run the gamut from a Classic Three Cheese with fontina, muenster, and Vermont cheddar between slices of Iggy’s pain de mie, to the Green Muenster, which ups the ante with bacon and house-made guacamole. Roxy’s also serves a trio of vegan grilled cheese sandwiches made with plant-based alts.

The Breakfast Grilled Crack from Mike & Patty’s piles fried eggs and two strips of bacon with melty cheddar, Swiss, and Gruyère on buttered-up sourdough bread. 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.

Allium Market & Cafe

The cheese pros helming Brookline indie food market Allium Market serve a stellar take on a GC that includes a house cheese blend between slices of rustic sourdough. An added dollop of chili jam brings the sweet and the heat.


As a satisfying alcohol sponge, the Grilled Cheese is truly in its element at Drink. But being a Barbara Lynch establishment, the Fort Point cocktail bar’s entry is anything but basic. It gets spruced up by heirloom tomatoes and basil pesto for extra layers of flavors.

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 grilled cheese gets fancy. The base option is a mix of cheddar and Gruyère on Iggy’s pain de mie, which you can further upgrade with onion jam, prosciutto, or Serrano ham.

Exterior of Cutty's

Brookline lunch counter Cutty’s is more or less dedicated to sandwich perfection, the Cutty’s Grilled Cheese included. In this instance, you’ll be treated to your choice of well-buttered white or wheat bread stuffed with Havarti and the option to include add-ons like ham, bacon, and fried shallots.

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