Grilled Pimento Cheese, Ham, and Homemade Pickles Sandwich Recipe

Savory piquillo-studded sharp cheddar spread, slices of ham, and scratch-made dill pickle chips make for a memorable grilled cheese.

By
María del Mar Cuadra
A headshot of Maria del Mar Cuadra, a contributing writer at Serious Eats.
María del Mar Cuadra is a food stylist, recipe developer, and art director. She has written three cookbooks and worked for America's Test Kitchen.
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Updated February 02, 2024
Closeup side view of a halved Grilled Pimento Cheese, Ham, and Homemade Pickles Sandwich.

Serious Eats / Maria del Mar Cuadra

Why It Works

  • Briefly warming grated onion, ground mustard, and Cayenne in a portion of the mayonnaise tempers the onion's harshness and blooms the spices for a savory, full-flavored pimento cheese.
  • Substituting bold and tart piquillo peppers for the usual pimento adds extra pepper flavor and balances the richness of the cheeses and mayonnaise.
  • Crisp, flavorful dill pickle chips are made in a fraction of the time by salting and draining sliced cucumber, briefly cooking the slices in vinegar, and then rapidly cooling them with ice cubes.

Pimento cheese is as Southern as that region's languid drawl, but oddly, it is not as well-recognized a food as some other tabletop offerings such as mint juleps. I say oddly because the vibrant cheese spread, flecked with finely chopped pieces of red pimento peppers is not only delightful, but a point of much secrecy, pride, and contention in the South.

Everyone acquainted with pimento (properly pronounced "pi-meh-nnah") cheese spread knows that its basic components are orange cheddar cheese, mayonnaise, and jarred or canned pimento peppers, but ratios, stir-ins, seasonings, and methods of making are particular to individual households and cooks who jealously guard their recipes. Cream cheese, hot sauce, cayenne pepper, grated onions, dry mustard, Worcestershire sauce, minced green olives, garlic powder—like the number of licks it takes to get to the center of a Tootsie pop, the world may never know what lies in one woman's (or man's) pimento cheese spread.

I find this type of secrecy funny and quaint, but come on now, let's play nice and share, shall we?

My pimento cheese spread has a solid foundation of orange cheddar, cream cheese, and... this is where the quirks and particularities begin. Judge me at will, but I opt for canned piquillo peppers rather than the spread's namesake pimentos. Too often, tinned pimentos are water-logged, bland, and flabby, and I suspect them of being roasted red peppers. Piquillos are smaller red peppers, packaged just the same, but somehow their flavor remains brighter, bolder, sweeter, and more tart: important attributes as they will be folded into a rich and fatty spread that needs to be cut through.

Self-confessed condiment fanatic that I am, I opt for as many of those optional additions as I can pack in. I've tasted raw onion and dry mustard in some pimento cheese spreads, and they need mellowing. Since the spread has mayonnaise for easier spreading, I melt a couple of tablespoons and cook the onion and mustard to soften and bloom them. This simple step gives the spread a distinctive, but not overwhelming, boost. Worcestershire, cayenne, and hot sauce provide backbone and enough heat to give your brow just the slightest hint of perspiration.

Pimento cheese is commonly served with crackers or celery sticks—you can make a batch of this and serve it at your next dinner party—but one of my favorite ways to eat it is in grilled cheese form. Crisp and buttery bread, gushing cheese, ham, and homemade pickles that are crunchy, sour, and fresh with chopped dill. If you're not acquainted with pimento cheese, you'll experience love at first bite, and, if it's old hat, you know exactly what I'm talking about.

April 2012

Recipe Details

Grilled Pimento Cheese, Ham, and Homemade Pickles Sandwich Recipe

Prep 15 mins
Cook 30 mins
Active 45 mins
Salting Time 60 mins
Total 105 mins
Serves 4 sandwiches
Cook Mode (Keep screen awake)

Ingredients

For the Pickles:

  • 4 Kirby (pickling) cucumbers, sliced crosswise into 1/4-inch thick slices

  • 1 tablespoon kosher salt

  • 1 cup fresh dill, chopped

  • 1 tablespoon black peppercorns

  • 1 tablespoon dill seeds

  • 1 tablespoon mustard seeds

  • 1 1/2 cups distilled white vinegar

  • 2 tablespoons sugar

  • 4 garlic cloves, peeled and smashed

  • 1/2 cup ice cubes

For the Pimento Cheese:

  • 4 tablespoons mayonnaise

  • 1 tablespoon finely grated yellow or white onion

  • 2 teaspoons dry mustard

  • 1/8 teaspoon cayenne pepper

  • 2 cups (8 ounces) extra-sharp orange cheddar cheese, finely grated

  • 4 ounces cream cheese, softened

  • 2/3 cup drained jarred or canned piquillo peppers, finely chopped (see note)

  • 1 tablespoon Worcestershire sauce

  • Salt and pepper

  • Hot sauce (optional)

For the Assembly:

  • 8 slices sturdy white sandwich bread (see note)

  • 6 tablespoons unsalted butter, melted

  • 12 slices deli ham

Directions

  1. For the Pickles: Toss cucumbers with salt in colander set over bowl. Allow to stand at room temperature for 1 hour. Discard all liquid released by cucumbers.

  2. Place 1/2 cup fresh dill, peppercorns, dill seeds, and mustard seeds in square of cheesecloth and tie together. Place spice bag in a medium saucepan along with vinegar, sugar, and garlic and bring to boil over medium-high heat. Add cucumbers and reduce heat to medium-low.

  3. Cook until cucumbers turn dark green, about 5 minutes. Transfer cucumbers and cooking liquid to bowl, add ice, and stir until melted. Chill, uncovered, at least 1 hour before serving. Discard spice bag and garlic and stir in remaining 1/2 cup fresh dill.

  4. For the Pimento Cheese: Melt 2 tablespoons mayonnaise in a small skillet over medium heat. Add onion, dry mustard, and cayenne and cook, stirring often, until onion is softened, about 3 minutes. Transfer to a large bowl and cool to room temperature, about 5 minutes.

  5. Add cheddar cheese, cream cheese, peppers, Worcestershire, and remaining 2 tablespoons mayonnaise to bowl and stir to thoroughly combine. Season to taste with salt, pepper, and optional hot sauce (see note).

  6. For the Assembly: Brush one side of each slice of bread with melted butter, then flip so that un-buttered side is facing up.

  7. Spread 1/4 cup pimento cheese on each slice of bread. Arrange 3 slices ham on 4 slices bread. Top ham with enough pickles to cover. Press remaining cheese-spread slices (cheese side down) over pickles.

  8. Heat large skillet or griddle over medium heat. Cook sandwiches until golden and beginning to ooze cheese, 2 to 3 minutes per side. Transfer sandwiches to cooling rack and allow to rest 2 minutes before cutting in half. Serve with additional pickles.

Special Equipment

Colander, medium saucepan, cheesecloth, pastry brush, large skillet or griddle, cooling rack

Notes

I prefer to use piquillo peppers because they are sharper, sweeter, and more flavorful than canned or jarred pimento peppers, but if you prefer pimentos, substitute them here.

For best results, use a sturdy loaf of bread, such as Pullman, and slice 3/4-inch thick.

Pimento cheese yields 2 cups, should you want to serve it on its own.

Make-Ahead and Storage

Pickles may be made up to 2 weeks ahead and stored, refrigerated, in a covered container.

Pimento cheese may be made up to 1 week ahead and stored, refrigerated, in a covered container. Bring the spread to room temperature prior to using or serving.

Read More

Nutrition Facts (per serving)
720Calories
46gFat
56gCarbs
23gProtein
×
Nutrition Facts
Servings: 4
Amount per serving
Calories720
% Daily Value*
Total Fat 46g58%
Saturated Fat 21g103%
Cholesterol 110mg37%
Sodium 1803mg78%
Total Carbohydrate 56g20%
Dietary Fiber 4g13%
Total Sugars 9g
Protein 23g
Vitamin C 30mg149%
Calcium 249mg19%
Iron 5mg28%
Potassium 613mg13%
*The % Daily Value (DV) tells you how much a nutrient in a food serving contributes to a daily diet. 2,000 calories a day is used for general nutrition advice.
(Nutrition information is calculated using an ingredient database and should be considered an estimate.)

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