Craving grilled cheese that goes way beyond bread and cheddar? You are in the right place. These spots layer on wild extras like mac, waffles, hot chicken, and even gourmet truffle mushrooms to make every bite unforgettable. Get ready to map out your next melty adventure across America, plus one Canadian curveball you will brag about later.
The Clevelander Bar & Grill – Cleveland, Ohio
In Cleveland, this neighborhood bar tucks hometown pride into every melty bite. Picture a grilled cheese stuffed with buttery pierogies, caramelized onions, and smoky kielbasa for that extra Cleveland comfort. The bread toasts up golden and crackly, while sharp cheddar and provolone fuse everything together.
You get a satisfying chew, a burst of onion sweetness, and just enough spice from the sausage. Order a side of stadium style fries and you will feel like game day never ended. Pair it with a local lager and you have a perfect Midwest feast.
Tom & Chee – Newport, Kentucky
Tom & Chee made the grilled cheese donut famous, and yes, it is as outrageous as it sounds. Imagine a glazed donut griddled in butter until caramelized, then layered with gooey cheddar or mozzarella for a sweet savory mashup. Dip it in tomato soup and the contrast becomes shockingly comforting.
You can build your own with extras like bacon, jalapeños, or fried pickles for crunch. The menu stays inventive without losing that childhood nostalgia you crave. Bring napkins, because the glaze and cheese combo gets thrillingly messy fast.
Barrel cheese & wine | cocktails | Event Space – Chicago, Illinois
Chicago’s Barrel takes grilled cheese into cocktail hour territory with smart pairings and luxe add ons. Think fontina and aged cheddar melted over truffle mushrooms on thick country bread, finished with a swipe of garlic aioli. Each bite lands earthy, creamy, and gently garlicky.
You can add prosciutto or a drizzle of hot honey for contrast. The staff loves recommending wines that cut through the richness without losing indulgence. Settle in at the marble bar, sip something sparkling, and watch that cheese pull glisten under moody lights.
Tartinery – New York, New York
At Tartinery, the French tartine meets American comfort in an open faced grilled cheese that feels chic and hearty. Raclette or comté pools over thick, crackly bread, with tangy cornichons and Dijon cutting through the richness. Add mushrooms or jammy onions for a deeper, Paris bistro vibe.
You will love the crisp edges and stretchy center that make each bite elegant yet familiar. Pair with a light salad or a glass of chilled white wine. It is proof that grilled cheese can be both simple and incredibly stylish in New York.
Roxy’s Grilled Cheese & Burgers – Central Square, Cambridge – Cambridge, Massachusetts
Roxy’s in Cambridge does grilled cheese with rock concert energy and serious technique. Their short rib packed melt drips with fontina and arugula, touched by hot honey for sweet heat. The bread is butter bombed and perfectly pressed, so every bite crunches.
Try adding a side of truffle fries or a pickle spear to slice through the richness. The staff keeps it upbeat and fast, which makes the lunchtime rush feel fun. You will walk out with a cheese high and plans to come back tomorrow.
The Cheese Shop – Williamsburg, Virginia
This Williamsburg staple nails classic comfort with Virginia character. A grilled cheese gets upgraded with sharp cheddar, local ham, and their iconic house dressing that adds peppery tang. The bread crisps just enough to hold the drippy cheese without losing softness.
Order it with a side of chips and a sweet tea to complete the moment. You will find the vibe unfussy, friendly, and happily nostalgic. It is the kind of place where one sandwich turns into a tradition you keep sharing with friends.
Cheesy Eddie’s – Rochester, New York
Known for desserts, Cheesy Eddie’s surprises with a grilled cheese that leans playful and sweet. Expect sharp cheddar and candied bacon layered with thin tart apple slices on buttery griddled bread. The balance of salty, sweet, and crisp keeps every bite exciting.
Ask for cinnamon swirl bread if you want a bolder contrast that tastes like fall. Pair with a cup of coffee or hot cider and settle into the cozy vibe. It is a sandwich that proves dessert shops can do savory delightfully well.
The Waffle Window – Portland, Oregon
Portland’s Waffle Window rewrites the rules by swapping bread for crisp Belgian waffles. Your grilled cheese becomes a crunchy, pocketed masterpiece filled with cheddar and fried chicken, finished with a light maple drizzle. Sweet, salty, and cheesy collide in the best way.
Vegetarians can sub in roasted veggies and extra cheese for an equally satisfying bite. The window service keeps things quick, but you will want a photo before diving in. It is a handheld festival of textures that makes traditional sandwiches feel tame.
Best In Show Events – Phoenix, Arizona
At Phoenix pop ups from Best In Show Events, the grilled cheese lineup goes full fiesta. Picture pepper jack and Oaxaca melting around roasted green chiles and elote style corn, showered with cilantro and lime. The heat is friendly, the cheese stretch generous.
Catch them at local festivals where the desert sunset makes everything taste brighter. You will smell butter on the griddle long before you see the truck. Grab two, because the first vanishes before you finish saying melted.
Mac Mart – Philadelphia, Pennsylvania
Mac Mart doubles down on comfort by stuffing a grilled cheese with creamy mac, then crowning it with crushed chips. The outside crisps up while the inside stays outrageously silky. Each bite lands like a childhood sleepover leveled up for grown ups.
Add bacon, hot sauce, or scallion sour cream for extra chaos. The line moves fast, so study the board and commit. You will leave with a grin and a carb glow that lasts all afternoon.
S’MAC – New York, New York
S’MAC takes their iconic skillet mac and transforms it into a pressed grilled cheese that is equal parts crunchy and gooey. Breadcrumbs add a toasty top note while cheddar and American melt into nostalgic bliss. It is messy, satisfying, and exactly what late nights require.
Customize with buffalo chicken, garlic, or vegan cheese if that is your lane. The counter crew knows the timing for that ideal crust. Grab extra napkins and a soda, then embrace the glorious cheese avalanche.
Stuff’D Grilled Cheese & Tots – ON M5T 2W6, Canada
Across the border, Stuff’D goes all in with poutine grilled cheese that feels delightfully over the top. Squeaky curds melt with cheddar while hot gravy soaks fries tucked between crisped bread. You get crunch, squeak, and saucy comfort in one handheld package.
Tots on the side push the theme even further. Ask for extra gravy if you live dangerously and do not mind drips. It is the joyful kind of chaos that turns a quick snack into a full Canadian experience.
Cheddar’s Scratch Kitchen – Orlando, Florida
Cheddar’s in Orlando turns the classic into a crunchy crowd pleaser by slipping a crispy chicken tender inside. A blend of melted cheeses binds everything while a honey hot drizzle adds kick. The bread gets griddled to golden perfection that cracks on the first bite.
Order a side of tomato soup or fries for dunking. The portion sizes lean generous, so you might share or proudly conquer it solo. Either way, you will leave satisfied and maybe plotting a repeat visit.
SPREAD & CO. – Austin, Texas
At SPREAD & CO., the Texas twist shines in a jalapeño jam kissed grilled cheese. Sharp local cheddar stretches, while optional smoked brisket lends deep, peppery richness. The sourdough crackles in a way that announces each bite before it lands.
Pair it with a bright side salad or a Topo Chico for sparkle. The vibe is cool and unfussy, perfect for slow mornings or laptop afternoons. You will chase that sweet heat balance long after the plate is clean.
Deli Board – San Francisco, California
Deli Board does everything loud, including a grilled cheese that eats like a deli legend. Imagine melted swiss and cheddar hugging thick pastrami, with pickled peppers for zing and Russian dressing for creaminess. The sandwich is hefty and unapologetic.
You will want a stack of napkins and maybe a friend to split it with. A side of slaw keeps things crisp and bright. This is the grilled cheese you order when you want to feel truly, happily stuffed.
Steuben’s Uptown – Denver, Colorado
Steuben’s brings diner charm to a modern grilled cheese with tomato jam and a whisper of green chile. The jam adds sweet tang while the chile supplies gentle warmth, all sealed in a cast iron sear. Expect a crisp shell and stretchy, molten middle.
Order a milkshake or a boozy float and go full retro. The staff nails timing so your sandwich arrives at peak ooze. It is comfort food with a Rocky Mountain wink that keeps you coming back.