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Where to Celebrate National Grilled Cheese Day in Westchester

Adobe Stock / George Dolgikh

If you’re looking for the top-shelf gooey goodness of grilled cheese, these eight Westchester eateries are sure to impress.

If the phrase ‘there’s beauty in simplicity,’ had a posterchild, it would be the humble, delicious grilled cheese. Despite being one of the easiest meals to make with the most basic of ingredients — so easy and basic, in fact, that even those who lack kitchen cred can cook one up in a jiffy — it’s been one of America’s favorite sandwiches for nearly 100 years.

Conceived during the Great Depression, these gooey sandwiches are a surefire way to put a smile on your face. Whether you’re looking to celebrate that history of cheesy goodness, or you’re just longing to reconnect with one of your favorite childhood craves, these eight Westchester restaurants are sure to hit the spot and impress even the most choosey of cheese connoisseurs.

105 Ten Bar & Grill

127 Woodside Ave, Briarcliff Manor; 914.236.3651

The first and flagship location of Westchester’s impressive 105 restaurant group, this Briarcliff Manor bar and grill has two separate grilled cheese options, both of which are sure to please guests of all ages. The first is a lobster grilled cheese, comprising a mix of cheddar, brie, and Swiss cheeses served on Texas toast with truffle oil and a side salad. The second option is a short rib grilled cheese, which includes cheddar, Swiss, and pepper jack cheeses on Texas toast with a tangy beer barbecue sauce.


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The Beehive

30 Old Route 22, Armonk; 914.765.0688

The Beehive has created quite the buzz around Armonk in its almost 18 years of operation, garnering acclaim for its balance of adherence to tradition and pursuit of a menu with contemporary flair. In the dinner lineup, The Beehive has two options for those looking to take their grilled cheese to the next level. The first is a more classic option named the “Ooey Gooey Grilled Cheese,” which is served on Greenleaf panini bread. The second is called the “Ultimate Grilled Cheese Bacado,” which includes applewood smoked bacon, avocado, and Cabot Monterey. Pro Tip: If you’re looking to add a healthy side to your grilled cheese (but abhor slaw or greens), be sure to ask about upgrading your fries to sweet potato wedges. You’ll be glad you did.

Mason Sandwich Co.

33 Mill Rd, Eastchester; 914.776.2766

This Eastchester mainstay is the final word in any discussion on where to find great craft sandwiches. Mason’s grilled cheese is made from a blend of Comte and Vermont white cheddar, served with creamy tomato soup on the side — long considered an inseparable companion to any great grilled cheese. For families who want to celebrate National Grilled Cheese Day together, there’s also a kid’s menu version which drops the tomato soup and eschews the aforementioned cheese blend in favor of good old-fashioned American.


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Mt. Kisco Diner

252 E Main St, Mount Kisco; 914.666.5676

For fans of the classic, no-nonsense grilled cheese, the Diner offers four different choices of cheeses (American, Swiss, mozzarella, or cheddar). For those who consider themselves too cool for old-school grilled cheeses, consider the “Grown-Up Grilled Cheeses” section of the menu. These monstrous creations run the gamut from the health-conscious Very Veggie (portobello mushrooms, fire-roasted potatoes, tomato, spinach, zucchini, Monterey, and aged cheddar on sourdough bread) to the wickedly gooey Loaded Grilled Cheese (aged cheddar, Monterey, Swiss, American, bacon, and tomato on thick country white bread).


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Put Some Meat on Your Bones

650 Lee Blvd, Jefferson Valley; 914.391.5527

If it’s wheely good grilled cheeses you’re after, then you’d do well to head to the Jefferson Valley mall to check out this popular food truck (which offers a sweet “pay what you can” deal). Put Some Meat on Your Bones has a distinct passion for grilled cheeses that rivals even the greatest. With 12 different flavors to choose from, there is truly something for everyone. Foodies who like it hot would find the turkey chipotle chili grilled cheese option perfect, while others who like it a la Italiana should check out the Mother Cabrini (mozzarella, sun-dried tomatoes, and basil).


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Second Mouse Cheese Shop

57 Manville Rd, Pleasantville; 914.579.2909

The go-to stop for discerning cheese addicts, Second Mouse is a unique eatery that is seriously and solely devoted to all things cheese — and the selection of grilled cheese sandwiches reflects this. The daily menu has three separate grilled cheeses, including: The Classic (a blend of cheddar and Alpine cheeses, served with mustard or bacon marmalade), The Hipster (Havarti melted atop roasted poblano peppers, green salsa, and arugula), and The Alpine (nutty and fragrant Alpine cheeses, organic kimchi, and sesame oil). All options are available on either organic French sourdough or local gluten-free bread.

Village Social

67 Purchase St, Rye; 914.612.4267

For a sandwich that eats like a meal, make haste to this local favorite for the luscious, satisfying short-rib grilled cheese, made with cheddar and slow-cooked beef sandwiched between slices of crisp sourdough bread.

The Wooden Spoon

16 Division St, New Rochelle; 914.278.9432

For a little help getting festive on National Grilled Cheese Day, The Wooden Spoon has a three-cheese grilled cheese offering that’s made with a mix of pepper jack, mozzarella, and cheddar cheeses on buttered Texas toast. Pro Tip: If you plan on bringing your kids with you, fear not: The Wooden Spoon also has a kids’ menu version which should bring a smile to their faces.


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Related: The Cheesiest Dishes in Westchester and Where to Find Them


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