Is tomato season over? It is. But is it too late to make Tomato Cheddar Pie? It is not! I have figured out how to hack tomatoes and turn spare grocery store tomatoes into the superstars they’ve always dreamed of becoming…which means any season is Tomato Cheddar Pie season!

I find this news very exciting, and I hope you do as well.

My Tomato Cheddar Pie begins with a biscuit-like crust made with cold butter and tangy buttermilk, which builds a tasty base for all the tomato-cheesy goodness we are going to pile on top of it.

Inside the buttery biscuit crust, we are going to layer slices of enhanced tomatoes (more on this in a minute), slight slathers of an herby sauce, and a shower of shredded cheddar cheese (the sharper the better in my opinion).

Then, we are going to bake this concoction until the juices are bubbling and thick, the cheese is charring on top, and the biscuit crust is golden brown and begging for you to snap off a craggy corner as a before-dinner snack. It’s dang good.

Now for the tomato magic.

When we slice fresh tomatoes, even perfectly ripe ones, there is an abundance of water. This is fine, except not in pie. In a pie, water creates a soggy mess. In order to reduce the water, you could slice and salt the tomato slices, draining them on top of paper towels until they give off some of their moisture. This plan works great when you are given home-grown tomatoes, sweet off the vine and ready to eat. But for most of the year, we are faced with sub-par gas-ripened grocery store tomatoes that will never be awesome. If we take the mealy tomatoes, slice them and gently dry them out in the oven, not only do they emerge less water-logged, but also concentrated in flavor. They taste completely different, worthy of being piled into a pie and baked for dinner.

This is the trick, the hack. Slice and roast your tomatoes. It will take the same amount of time as it will take you to throw together the crust, and the results will change your opinion of the viability of out-of-season tomatoes.

Ingredients

for the tomatoes…

2 pounds plum tomatoes, cut into 1/2-inch slices (each tomato should yield 4-5 slices)
2 tablespoons olive oil
2 teaspoons Kosher salt
1 teaspoon freshly ground black pepper

for the crust…

2 cups all-purpose flour
1 1/2 teaspoon baking powder
1/2 teaspoon baking soda
1/2 teaspoon Kosher salt
6 tablespoon chilled unsalted butter, cut into cubes
1 cup buttermilk

for the filling…

1/2 cup mayonnaise
1 green onion, chopped
1 tablespoon chopped fresh dill
2 tablespoon chopped fresh basil
1 tablespoon apple cider vinegar
2 teaspoons sugar
3/4 teaspoon Kosher salt
1/2 teaspoon freshly ground black pepper
8 ounces grated sharp cheddar cheese
2 ounces finely grated Parmesan cheese

Instructions

Preheat the oven to 400 degrees. Place the sliced tomatoes in a single layer on a sheet tray. Drizzle with the olive oil, Kosher salt, and pepper. Roast for 45 minutes. They should be shrunken, a bit shriveled, and there will be some liquid on the sheet tray. This is perfect!
While the tomatoes roast, make the crust. In a medium-sized bowl, whisk the flour, baking powder, baking soda, and salt until combined. Add the cold, cubed butter and use your hands to smash each cube and rub it with flour. Continue doing this until the butter is incorporated and the mixture has a crumbly consistency. Add the buttermilk and combine (either with your hands or a strong wooden spatula) until a shaggy dough forms. It will be a bit sticky. Place the bowl in the fridge while you mix up the filling to keep the butter cold.
In a small bowl, combine the mayonnaise, green onion, dill, basil, vinegar, sugar, salt, and pepper.
In another small bowl, combine the cheddar and parmesan cheese.
Once the tomatoes have come out of the oven, and everything else is made, you are ready to assemble the tomato pie. Change the oven temperature to 425.
Dump the dough out onto a floured board and knead it a few times with your hands until it comes together. Gently pat or roll it out into an 11-inch round. Carefully transfer the dough to a glass or ceramic pie dish. You should have some dough hanging over the edge of the pie plate. I like to use a deep-dish pie plate for this recipe, but a standard pie plate will work too.
Before you begin to assemble, reserve about 1/4 cup of the cheese mixture to sprinkle on top.
Layer the pie as follows: 1 cup of the cheddar parmesan mixture, one third of the tomato slices, half of the mayonnaise mixture, 1 cup of the cheddar parmesan mixture, another third of the tomato slices, the remaining mayonnaise mixture, 1 cup of the cheddar parmesan mixture, the remaining third of the tomato slices, and the reserved 1/4 cup of the cheddar parmesan mixture.
Fold the overhanging crust up and over the edges of the tomato slices. Bake the pie until the crust is golden and the cheese is browned on top, approximately 30 to 45 minutes. Allow the pie to cool for at least 1 hour, or up to 3 hours, before slicing and serving.

Notes

If you happen to find yourself with delicious, vine-ripened tomatoes in the height of tomato season, skip the roasting step of this recipe. Instead, line a sheet tray with a double layer of paper towels, slice the tomatoes, place them on the paper towels, and allow them to drain for about 30 minutes. Proceed with the rest of the recipe as written.

Tomato Cheddar Pie