3 Killer DIY Grilled Cheese Sandwiches

Deep in the bleak, bone-chilling days of winter, we adults need a booster of gooey, nostalgic grilled cheese just as much as the kids do.

By Benjamin Tepler January 5, 2015 Published in the January 2015 issue of Portland Monthly

In lieu of American singles on Wonder Bread, we tapped the city’s experts, Nick Dickison and Carina Rumrill, formerly from the food cart Cheese Plate PDX, for their coziest, locally sourced formulas. (Each recipe makes four sandwiches.) The ingredients are all grown up, but the results, we promise, will make you feel like the luckiest kid alive.

Editor's Note: Dickison and Rumrill closed the cart in 2015 to open the Sundays-only vegan pop-up, Of Roots and Bloom. But in its prime, Cheese Plate’s most popular offering featured two cheddars for intense tang, melded with cold-weather comfort flavors. 

Top: The Cheddar Brussels

  • Sourdough levain (Fleur de Lis)
  • Aged cheddar (Face Rock Creamery)
  • Medium cheddar (Tillamook)  
  • Brussels sprouts: Heat 1 tbsp olive oil over high and sauté ½ cup thinly sliced brussels sprouts for 3–4 minutes, or until soft and beginning to brown. Sprinkle with salt and pepper.  
  • Sage Aioli: Combine ¼ cup mayonnaise, 1 tsp finely chopped fresh sage, and 1 clove garlic, finely chopped. Add lemon juice, salt, and pepper to taste. 

Middle: The Whiskey Pear

A decadent smoky-salty-sweet trifecta featuring some of Portland’s top artisans

  • Brioche (Fressen Bakery)
  • Fontina (Willamette Valley Cheese)
  • Goat cheese (Portland Creamery)
  • Whiskey caramel (Alma Chocolate)  
  • Smoked salt (Jacobsen Salt Co)
  • Pear: Heat oven to 350 degrees. Quarter 1 large ripe pear lengthwise and remove core. In an ovenproof skillet, heat 1 tsp olive oil over high heat and sauté the pears with a pinch of salt for about a minute, or until beginning to brown. Add 2 tbsp white wine to the skillet and roast in the oven for 10 minutes. Remove and let cool completely. 

Bottom: The Blue Fig

The classic fig-and-blue-cheese combo gains a sharp nuttiness from aged gouda and an earthy sweetness from caramelized onions.

  • Walnut bread (Gabriel’s Bakery) 
  • Blue cheese (Rogue Creamery) 
  • Boerenkaas (Willamette Valley Cheese)
  • Fresh fig jam (Three Little Figs Balsamic)
  • Caramelized onions: Heat 1 tsp butter and 1 tsp olive oil in a heavy-bottomed pan over high heat. Add 1 yellow onion, diced, with a pinch of salt, and stir frequently until onions begin to brown. Reduce heat to medium-low and cover, stirring occasionally, until caramelized, about 20–30 minutes. 

How to Make the Perfect Grilled Cheese, Every Time

  1. DOUBLE DOWN: At least two cheeses are needed for any great grilled cheese: one melty (cheddar, fontina, havarti), and one textured (goat cheese, gouda, parmesan). For even melting, grate your cheese whenever possible, rather than slice it.
  2. BUTTER UP: Use good-quality, salted butter at room temperature—it’s easier to spread. Butter the bread, not the pan, conservatively to avoid a greasy mess.
  3. LOW AND SLOW: Keep your flame at medium-low. Grill one side in a skillet until golden, flip the sandwich, and put some weight (any small, metal pot lid) on top so the fillings mesh. 
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