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Award-Winning Tomato Sandwich

By August 22, 2023No Comments

The classic southern tomato sandwich gets a few additions to make this a sandwich you'll want to enjoy on a weekly —if not daily— basis.

The Botetourt Farmers Market hosted their first annual Tomato Festival in 2021. Below you’ll find the recipe for my award-winning* specialty tomato sandwich. This recipe is fantastic for using up a bumper crop of cherry tomatoes. As an added bonus, you’ll have plenty of leftover confit and aioli to use on all of your favorite summer dishes!

My father, the self-dubbed “Tomato King,” taught me early on how to make the perfect tomato sandwich. This manifested in my gold medal in the “Classic” category, in which the only accepted ingredients are bread, tomato, salt and pepper, and mayo (Duke’s is supreme, talk to the gold medal if you disagree…). I also entered into the “Freestyle category”, where my creation was described as “the taste equivalent of when someone else cancels plans that you didn’t want to go through with.” This remains one of the greatest culinary compliments I may ever receive. Make this sandwich and be the judge yourself!

*2nd place

Recipe by Jesse Feldberg, Roanoke



2 pints cherry tomatoes of your choice

5 cloves garlic, peeled and lightly smashed

2 medium shallots, peeled and quartered

1 tablespoon fresh oregano leaves (or ½ that amount dried)

½ tablespoon fresh thyme leaves (or ½ that amount dried)

½ tablespoon fresh rosemary leaves (or ½ that amount dried)

¼ cup olive oil

Salt and pepper


1 cup mayonnaise

1 tablespoon lemon juice

1 clove garlic, microplaned

1 tablespoon fresh oregano, finely chopped

½ teaspoon smoked paprika


2 slices rich white bread, lightly toasted (I recommend the pain de mie from Breadcraft Bakery) 

Thick-cut local bacon 

Spicy greens ((arugula, mizuna, tatsoi, etc. )

Fresh slicing tomato (I like to use a nice yellow tomato)

Fresh herbs to taste


Preheat your oven to 325℉. Arrange the tomatoes, garlic, and shallots on a baking sheet. Distribute the herbs throughout the sheet and drizzle with olive oil. Roast in the oven for 45 minutes, turning the sheet and lightly shaking it halfway. Once cooled, transfer to a food processor or blender, add salt and pepper to taste and blend to desired smoothness. I leave mine a bit on the chunkier side. Blend it further to make a great salad dressing base! 

While the confit roasts, prepare the aioli: whisk oregano, garlic, paprika and lemon juice into the mayonnaise and set aside. Cook the bacon to your liking. Once the confit is ready, it’s time to build your sandwich. Slather a nice layer of aioli on the lightly toasted bread, then add your bacon, fresh tomato slices, a healthy portion of confit, and top with spicy greens. Serve with an extra side of confit for dipping!

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